People Ops: Lessons in Culture and Leadership From Building Startups 1484298187, 9781484298183

Citation preview

People Ops Lessons in Culture and Leadership From Building Startups ― Patrick Caldwell

People Ops Lessons in Culture and Leadership From Building Startups

Patrick Caldwell

People Ops: Lessons in Culture and Leadership From Building Startups Patrick Caldwell London, UK ISBN-13 (pbk): 978-1-4842-9818-3 https://doi.org/10.1007/978-1-4842-9819-0

ISBN-13 (electronic): 978-1-4842-9819-0

Copyright © 2023 by Patrick Caldwell This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed. Trademarked names, logos, and images may appear in this book. Rather than use a trademark symbol with every occurrence of a trademarked name, logo, or image we use the names, logos, and images only in an editorial fashion and to the benefit of the trademark owner, with no intention of infringement of the trademark. The use in this publication of trade names, trademarks, service marks, and similar terms, even if they are not identified as such, is not to be taken as an expression of opinion as to whether or not they are subject to proprietary rights. While the advice and information in this book are believed to be true and accurate at the date of publication, neither the authors nor the editors nor the publisher can accept any legal responsibility for any errors or omissions that may be made. The publisher makes no warranty, express or implied, with respect to the material contained herein. Managing Director, Apress Media LLC: Welmoed Spahr Acquisitions Editor: Shivangi Ramachandran Development Editor: James Markham Editorial Project Manager: Shaul Elson Cover designed by eStudioCalamar Distributed to the book trade worldwide by Springer Science+Business Media LLC, 1 New York Plaza, Suite 4600, New York, NY 10004. Phone 1-800-SPRINGER, fax (201) 348-4505, e-mail [email protected], or visit www.springeronline.com. Apress Media, LLC is a California LLC and the sole member (owner) is Springer Science + Business Media Finance Inc (SSBM Finance Inc). SSBM Finance Inc is a Delaware corporation. For information on translations, please e-mail [email protected]; for reprint, paperback, or audio rights, please e-mail [email protected]. Apress titles may be purchased in bulk for academic, corporate, or promotional use. eBook versions and licenses are also available for most titles. For more information, reference our Print and eBook Bulk Sales web page at http://www.apress.com/bulk-sales. Any source code or other supplementary material referenced by the author in this book is available to readers on GitHub (https://github.com/Apress). For more detailed information, please visit https://www.apress.com/gp/services/source-code. Paper in this product is recyclable

Table of Contents About the Author��������������������������������������������������������������������������������vii Preface������������������������������������������������������������������������������������������������ix Chapter 1: Building from Scratch���������������������������������������������������������1 Ground Your Decision-Making�������������������������������������������������������������������������������3 Simple Is Sexy�������������������������������������������������������������������������������������������������������5 Done > Perfect������������������������������������������������������������������������������������������������������6 Self-Service FTW��������������������������������������������������������������������������������������������������8 Decision by Committee Sucks����������������������������������������������������������������������������10 Beware the Magpies�������������������������������������������������������������������������������������������12 Your People Strategy Is Your Business Strategy�������������������������������������������������14 Summary������������������������������������������������������������������������������������������������������������15

Chapter 2: Leadership������������������������������������������������������������������������17 Red Flag 1: Lack of Leadership���������������������������������������������������������������������������18 Red Flag 2: The Wrong Leaders��������������������������������������������������������������������������21 Red Flag 3: Accidental Leaders���������������������������������������������������������������������������22 Not Everyone Wants to, or Should, Be a Leader��������������������������������������������������23 The Psychological Safety of Leaders������������������������������������������������������������������24 If Difficult Conversations Don’t Affect You, You Shouldn’t Be Having Them��������26 Sometimes to Show You Care, You Need to Show Your Teeth�����������������������������28 Summary������������������������������������������������������������������������������������������������������������29

iii

Table of Contents

Chapter 3: Culture�������������������������������������������������������������������������������31 Culture Is Not Free Beer, Fruit, and a PlayStation�����������������������������������������������31 Culture Contribution or Culture Fit����������������������������������������������������������������������32 What Does Autonomy Look Like for You?������������������������������������������������������������35 Process: The Enemy or the Hero?�����������������������������������������������������������������������37 Cut Only When Is Absolutely Necessary to Survive���������������������������������������������39 Find a Common Language����������������������������������������������������������������������������������43 Getting Past the Values Fluff�������������������������������������������������������������������������������45 Summary������������������������������������������������������������������������������������������������������������47

Chapter 4: Inclusion���������������������������������������������������������������������������49 Inclusion > Diversity�������������������������������������������������������������������������������������������50 Pitch at 80%��������������������������������������������������������������������������������������������������������53 Be Judged by Your Actions, Not Your Intentions��������������������������������������������������54 Get Under the Skin of Your Gender Pay Gap��������������������������������������������������������55 The Myth of Removing Bias��������������������������������������������������������������������������������60 Summary������������������������������������������������������������������������������������������������������������61

Chapter 5: Recruitment����������������������������������������������������������������������63 Respond to Every Single Job Applicant As Though Your Brand Depends on It����64 Start with Your Best Offer and Don’t Budge��������������������������������������������������������66 Your Candidate Experience Is As Important As Your Customer Experience���������69 Turn the Tables����������������������������������������������������������������������������������������������������71 Don’t Join This Company If…�����������������������������������������������������������������������������71 The Candidate Was Great! I’d Like to Meet a Few More Though�������������������������72 Summary������������������������������������������������������������������������������������������������������������74

iv

Table of Contents

Chapter 6: Reward������������������������������������������������������������������������������77 Design for the 99%���������������������������������������������������������������������������������������������77 Pay Transparency������������������������������������������������������������������������������������������������82 The “Pay Me More or I’ll Leave” Ultimatum��������������������������������������������������������88 The Law Is the Floor��������������������������������������������������������������������������������������������91 All Benefits Are for Day 1������������������������������������������������������������������������������������92 You Probably Won’t Retire Early Because of Equity��������������������������������������������93 Minimum Leave, Not Unlimited Leave�����������������������������������������������������������������99 Summary����������������������������������������������������������������������������������������������������������100

Chapter 7: Learning��������������������������������������������������������������������������103 Water Your Plants����������������������������������������������������������������������������������������������103 Learning Is About Experiences, Not Just Knowledge����������������������������������������107 The “Best” Career Advice I Ever Received��������������������������������������������������������109 Approach with Planning: Peer Feedback����������������������������������������������������������113 The Perfect Resignation: When the Time Is Simply Right���������������������������������115 Summary����������������������������������������������������������������������������������������������������������116

Chapter 8: Performance��������������������������������������������������������������������117 The Trinity: What, How, Where?�������������������������������������������������������������������������117 I Messed Up OKRs, Twice!���������������������������������������������������������������������������������120 People Outgrow Startups; Startups Outgrow People����������������������������������������122 If I Hear “Hire Slow, Fire Fast” One More Time…���������������������������������������������125 The Death of Performance Reviews?����������������������������������������������������������������127 Summary����������������������������������������������������������������������������������������������������������132

v

Table of Contents

Chapter 9: Remote Working��������������������������������������������������������������135 The Covid-19 Acceleration��������������������������������������������������������������������������������135 Remote Work Is Uncovering Our Dirty Laundry�������������������������������������������������136 Know the Difference Between Flexible and Remote Work��������������������������������139 The Remote Manager����������������������������������������������������������������������������������������141 Burnout Is Our New Thanos������������������������������������������������������������������������������143 Summary����������������������������������������������������������������������������������������������������������144

Chapter 10: Your Career�������������������������������������������������������������������147 Know the Difference Between Who You Are and What You Do��������������������������147 Be Clear on What Your Role Is and What It Isn’t������������������������������������������������149 “I Don’t Know”��������������������������������������������������������������������������������������������������150 Find Your Outlet�������������������������������������������������������������������������������������������������151 Be Ruthless with Your Time������������������������������������������������������������������������������153 Everyone Is a People Expert������������������������������������������������������������������������������156 It’s Great to Experience a Truly Shit Company at Least Once����������������������������158 Scaling Part 1: Keep Your Team As Small As Possible���������������������������������������159 Scaling Part 2: Make Yourself Redundant���������������������������������������������������������163 Summary����������������������������������������������������������������������������������������������������������164

Chapter 11: TL;DR�����������������������������������������������������������������������������167 Too Long; Didn’t Read: A Summary of Text That Was Too Lengthy��������������������167

Index�������������������������������������������������������������������������������������������������179

vi

About the Author Patrick Caldwell is a multi-startup People & Operational leader with experience in leadership teams and boards across Australia, the United States, and Europe. Pat is currently building out the first people and culture strategy as the Chief People Officer at Send, an InsurTech software company in the UK, and also serves as a Non-Executive Director on the board of ImpactEd, an EdTech scale-up helping purpose-driven schools, educational institutions, and partners with high-quality evidence and evaluation to improve outcomes for young people. Hailing from the coal mining industry in Australia, Patrick was formerly the COO at FundApps, an award-winning B Corporation, and the VP People & Operations at Metomic, an innovative cybersecurity technology startup.

vii

Preface “Patrick should consider if HR is right for him. He seems frustrated most of the time.” My first reaction was “pfft, whatever” to this gem from a 360 assessment. I wouldn’t have been so frustrated if I felt like we were actually having a positive impact on people. But I wasn’t. I was churning through spreadsheets, lists of policies, and the odd disciplinary that made up my days in what was jokingly (not really) known by a supervisor as the Human Remains department. Honorable mention to his second favorite name, the Hardly Relevant department. This isn’t an exception. This is still what the vast majority of people experience and come to expect from their HR department. The people you speak to when something is wrong, or better put, the people you hope to not need to speak to. Despite years of incremental change, we haven’t yet shaken the compliance-driven, “on the employer’s side,” back-office shadow that we’ve cast into businesses. And maybe we never will, at least completely. But this isn’t a book to bash HR, as therapeutic as part of me might find that. It’s a book about what HR is becoming and the transformation of how we think about people and culture. We’re part of a generation of teams, leaders, and businesses demanding an entirely new breed of capability around people and culture. We’re becoming People teams, relentlessly focused on how we engage, develop, empower, and recognize people and how our obsession with culture and the people experience can drive businesses to success.

ix

Preface

I fundamentally believe in the coming years we’ll see People functions entirely replacing what we’ve come to associate with traditional HR. Some of that work will still need to be done, but it won’t be the purpose of the People team, or how we add the most value to a business. We’ll no longer be just partners and advisors to a business either. We’ll be in the business and working on the business. We’ll treat our recruitment and onboarding experience with the same focus, care, and attention that we do our sales pipeline. We’ll be fully in sync with our people and looking for ways to increase their success and nurture relationships in the same way our customer success teams do. We’ll be working cross-functionally to design and iterate our work in the same way we expect our Product teams to. And we’ll be armed with the same tools and data insights that we’ve come to expect from our technology teams. My first experience with what is now demanded from People teams came in startups. It’s not exclusive to startups, and they can receive a disproportionate level of recognition around innovation in the people space simply because they’re not the stereotype of a large business (shout out to the People innovators in big businesses too!). Startups are, however, a really insightful test for what will be in the years ahead. In startups, every founding and leadership team experiencing growth will at some point make a decision to introduce a People capability into their team. There’s no baggage with this decision and usually no existing team, processes, or ways of working that influence what a People team can be in their business. Startups allow us to see how leaders answer this question: When you can build it from scratch, what do you aspire for the People team to be? As I transitioned from the world of HR to the world of People, I also met some truly incredible folks in both People roles and elsewhere in the business, who have helped shape my perspectives and work for how we engage, develop, empower, and recognize people. As passionate as I may be about both people and culture, I’ll never be an expert and I don’t think

x

Preface

that’s possible anyway. We’re constantly learning, adapting, and changing how we think about people, and keeping up with that by itself, let alone in high-growth startups, is a thrilling challenge. It also means I’ve had to learn things the right way – by doing them. Sometimes they worked, and a lot of the time they didn’t and I had to iterate my thinking and approach. As quite a reflective person, I also found myself making mental notes along the way. Things I observed, suggested, struggled with, worked on, screwed up, or smashed out of the park all made their way into my mental notes in the hope they might prove useful the next time I was faced with a similar scenario. Over time, these mental notes became written notes, throughout a myriad of notebooks, journals, and eventually a Notion page of stuff I didn’t want to forget. What you’ll find in this book are those mental notes I made along the way. This is not a book bursting with management theory and frameworks, rather a collection of stories, personal principles, and lessons learned. It’s grounded in my experience and the experience of those I’ve been fortunate enough to work with. I wrote these mental notes for me, but I’m sharing with you in the same way I might if we were chatting at the pub. And while every business is different, I hope there is something in here for everyone at whatever stage you are. If you are like me and have a short attention span, or don’t read books cover to cover, I’d highly recommend starting with Chapter 11. —Pat P.S. It turns out HR was not right for me. But I think People Ops might just be.

xi

CHAPTER 1

Building from Scratch If you’ve joined a startup, or even interviewed at one, you’ll likely have been sold the utopia of building on a blank canvas. That we have no processes in place, no playbook to make our success repeatable, no idea what we’re even doing. OK, maybe not that last one, but I’ll come on to that later and why it wouldn’t be such a bad thing to tell people up front. As incredible and liberating as a blank canvas sounds, it’s a myth. Don’t get me wrong, I still get warm fuzzies anytime I think about building things from scratch in a startup. But unless you are a founder starting a company, there is no such thing as a blank canvas. The canvas is already sprawled with paint around culture and leadership – existing beliefs, norms, ways of working, expectations, personalities, conflicts, highs and lows of everything that has happened before you showed up. The paint might not look like a work of art, but it’s already there whether you like it or not. There are an endless number of ways that paint can be sprawled across the canvas, but here’s a selection of some of my favorites from my early days within various startups: •

The hiring engine that takes place through “who do we know who could do this?” rather than “how will we find someone who will be awesome at this?”

•

Having no onboarding process because great people onboard themselves.

© Patrick Caldwell 2023 P. Caldwell, People Ops, https://doi.org/10.1007/978-1-4842-9819-0_1

1

Chapter 1

Building from Scratch

•

The employee who earns half of what they are worth on the market but operates under the belief that in five years the startup will be a unicorn and they can cash out on their equity and retire early.

•

Justifying the lack of job descriptions with the fact people wear lots of hats in a startup.

•

The founder who believes every employee who joins should be as deeply invested and committed to the cause as they are.

•

The promotion of a mid-level individual contributor to CxO after six months because they know the product well.

•

And, my favorite one, believing that they have a learning culture because a few developers went to a conference last year. Sound familiar? At the start of my time with every high-growth startup I’ve joined, there’s a period for several weeks when I try to actively observe the paint on the canvas. This is harder than it sounds, but the benefit of being so new to a company is that you’re viewing that canvas from the perfect angle. You haven’t been involved at all in painting it, so you have that beautiful mix of objectivity and curiosity. In a short while, that objectivity is mostly gone and you’re now also painting the canvas and getting stuff done. For the next few months, the key to surviving a startup is to find the balance on getting stuff done today and keeping one eye on what’s coming next. You need to be tactical enough to stay off the “not right for this stage of our growth” list, but thoughtful and strategic enough to be on

2

Chapter 1

Building from Scratch

the “grow with us” list. And so here seems the logical place to start sharing some of my musings with the hope you might make at least one less mistake than I have.

Ground Your Decision-Making I often wish managing people and building teams was more black and white. Instead, we’re faced with various shades of gray and expected to navigate through that with ease. Good judgment is important, but by itself judgment can be too easily confused with an opinion. What makes this easier is how you anchor your judgment in relevant data and information. One of the frogs I try to eat very early in my time at any startup is compensation. If the startup is bootstrapped, we have to operate within very tight cash restrictions and that means making educated and informed judgments on where we get the most bang for our buck when it comes to compensation. If the startup is backed, the same principle should apply too but with a wee bit more flexibility if the pockets you have are deeper. Compensation is deeply emotional. If you’re in the tech industry, it’s going to be the biggest area of your spend. If you’re in another industry, it’ll be one of the top three areas of spend. So getting it right is critical. But that’s just the company side of compensation. For us as individuals, we don’t really care how much of the P&L is dedicated to compensation. We just care about how much we get and whether it meets a few criteria around right and wrong: •

Expectations: Does it seem right based on what I’m expected to do? I’ve lost track of the number of negotiations where the basis of the ask is their gut feel on whether the package seems like it fits with the role.

3

Chapter 1

Building from Scratch

•

Lifestyle: There are two points to this to be mindful of: What was I earning previously and is this the same or better? And what sort of lifestyle am I trying to live or uphold? A software engineer from a big tech company on $300k per year with a lifestyle around this is going to find your offer of $200k to be unwelcome regardless of how much data exists.

•

Status and sense of worth: Never underestimate this. It’s normal, human, and common to find a sense of worth in our salary. For some people, it’s inconsequential. For others, it’s everything!

•

Fairness: I’ve framed most of the preceding criteria in the context of a new starter considering their compensation, but the fairness criterion is one of the most vital considerations for the existing team. If you’ve been in your role for a year, perhaps you had a small bump recently, and you find out a new team member doing the same role has joined and has a higher pay than you, you’re likely going to be pretty down about that regardless of their background.

I used to believe I could architect a perfect, data-backed model for startup compensation. I’ve tried a few times, and each time I ended up realizing something really important. Everyone supports a data-driven approach to compensation, until the data conflicts with what they want to be paid. Over time, I started to accept that a bit of art in compensation was never a bad thing – 80% science, 20% art. Put principles around how compensation is determined and use data and benchmarks to inform that. Use compa ratios or compensation ranges to build fairness into routines. And, most importantly, communicate transparently with the team and external candidates how compensation is set and reviewed. 4

Chapter 1

Building from Scratch

Not everyone will be a fan of this. Frankly, it’s usually the people who benefited from what the system used to be. But achieving 100% support is not the point here. You’re optimizing for something that creates fair, equitable, and consistent compensation outcomes and sometimes that means some tough reality checks for people. The key here is that having your decision-making grounded in something objective, with a small amount of flexibility to cater for the realities of such an emotional and complex topic.

Simple Is Sexy There is a certain urgency that people challenges tend to instill in a startup. Unfortunately, urgency has a knack for distorting decision-making toward the short term and that often comes back to bite you in the ass. Let’s consider recruitment. You need to grow fast! You feel the pressure from hiring managers. You find an amazing candidate who at the offer stage wants to negotiate some bespoke terms in their contract like a guaranteed bonus or a higher notice period. Maybe a different health insurance package or some nuance in their commission plan. Agreeing to these sorts of changes is often made out to be insignificant. A small price to pay to land a candidate and fill that role you’ve been trying to for ages. Let’s now add double- or triple-digit growth on top of that. Your team of 80 is now 240 and you have the complexity of individual terms and conditions to be administered on a much larger scale. It means the teams and infrastructure needed to administer that complexity grow with it. And don’t forget that people talk. So Joe will find out eventually that he has a less attractive commission structure than Sally, and Sally will learn that Kate has a benefit that you asked for but were told you couldn’t have. You get the point. Simple is sexy. And grossly underrated.

5

Chapter 1

Building from Scratch

When it comes to employment terms in a growing company, there is a lot to be said for simple, consistently applied terms across the broadest remit possible – that includes notice periods, leave entitlements, benefits, commission plans, bonuses, and anything else you might expect to be negotiated into an employment contract. There will always be some variability due to regional differences if the team grows globally, so if you have the luxury to join a company early before a period of hyper-growth, consider what the default offering looks like across as many employment terms as possible and don’t budge.

Done > Perfect Outside of startups, there’s a fairly common way of working in the People space. You table ideas and put together proposals with hope that senior leaders will approve it. You write extensive business cases justifying ROI and book meetings with key stakeholders looking for feedback and ambassadorship. You’ll have a communication strategy in place which in turn will generate communication and implementation plans. And finally, you’ll have a feedback and review cycle on your initiative to remind senior leaders of how well it’s performing. I used to work in this way. For years. I know of a number of people who have built their careers around their ability to thoroughly and methodically plan for every circumstance and they rarely spend time actually executing. Then I ended up in startups where most of that work is more insignificant than I cared to recognize. I’m not suggesting engaging stakeholders and being thoughtful about strategy isn’t important, just that the difference between a good initiative and a near-perfect initiative is of very little consequence in a startup. It’s likely why we’ve ended up with so many “get shit done” company values that prioritize execution and pace.

6

Chapter 1

Building from Scratch

In startups, having something in place that’s about 80% done is of far more value to the company than waiting weeks or months until it’s perfectly complete. The more potent realization for me was that anything you build you’ll likely need to upgrade or replace a number of times anyway as the company grows. After all, if you’re doubling headcount year on year, what you build in year one for 100 people is likely going to need a lot of iterating to still be effective for 400 people in year two. There is undoubtedly a long line of “but what about this?” considerations. The goal of prioritizing done over perfect is not about neglecting some of the key steps to change, in particular around communication, engagement, and influencing leaders. The goal is to get the initiative to a point where it’s solving a problem or delivering value, and then approaching it with a mindset to iterate and improve once it’s in place. Here are a few things to clarify early to set this up for success: 1. Is the initiative aligned with what the company is trying to achieve? There are 10,000 things we probably could be doing. Find the two to three most important ones that help the company achieve its goals. This will speed up how you engage and influence. 2. How will you communicate the initiative in a few different ways? Skip the vanity social media posts and five-slide cascading communication plan. The key here is to answer the question: How will every team know about this? In many startups, a combo of async messaging tools, all-hands and stand-up routines, intranet pages, and a bit of rinsing and repeating will do the trick.

7

Chapter 1

Building from Scratch

3. Do you have a rough idea what success looks like? This needn’t be a set of objectives and a pyramid of key results. What’s the most important thing you’re solving for and how will you know you’ve done that? Focus on that when you’re communicating to leaders and the team. 4. How will you set expectations? In a number of startups, I’ve used the symbol of a naming convention to many of the bigger initiatives. Parental Leave 3.0. Reward 4.0. Leadership Development 2.0. It’s designed to represent iterations and over time becomes a symbol for every initiative being considered as an improvement area in the months and years to come.

Self-Service FTW There’s a small window in the early days of startups where you can get away with highly unscalable solutions. In fact, there’s a lot to be said for why you should embrace unscalable solutions for as long as possible especially if there’s a highly personal and human component to it. When you have 10 or 20 employees in your startup, you might not be too concerned with managing leave in a spreadsheet, recruitment through emails, and processing the odd expense claims when someone in the team sends you a photo of their stand-up desk receipt. I’m not sure exactly where the threshold is, but there’s a point in growing the team when the burden of this administrative work becomes too much of a distraction on people in the company who are likely managing people stuff in addition to their core roles. The most common answer to this is “let’s hire someone to do the work” which, despite the excitement that growing a team involves, is often just managing a symptom of a growing team rather than the problem 8

Chapter 1

Building from Scratch

itself. The question is not “who manages this work” or “how do we cope with increased administrative work” but rather “how do we reduce the administrative overhead our growing company is producing.” Hiring is still a possible solution, but it’s the last possible solution as the goal is ultimately to keep the smallest team for as long as possible. For a lot of the administrative work a growing startup encounters – expenses, leave, payroll, access to systems, etc. – I’ve found a lot of success in using tools to drive self-service. Allowing team members to manage their own administrative workload in a clear and accessible way, supplemented with tools that automate as much of the process as possible. There are cheap, even free, HR tools on the market to administer leave and benefits including payroll inputs. Similarly, automation workflows can help support onboarding and offboarding procedures and distribute actions automatically across the team after a trigger is passed. Central knowledge management tools provide a single source of documentation and process so that the team can self-serve the “know-how” of the company which saves a lot of back and forth communication and even the need to run training sessions sometimes too. The outputs of this work will still exist but only a fraction of the work that originally existed, so this can either still sit as part of someone’s role or can be outsourced to an accountancy, payroll, or virtual assistance company for a few hours per week. There will still come a time where the People, Finance, and Operations areas will need dedicated in-house capability, or at least fractional where more strategic work is needed, but putting in place efficient tooling that automates administrative work and encourages self-service will delay that need which is important. It will also mean that when the time comes to hire into these teams, there is space for a more strategic hire that can focus on the highest value initiatives to the success of the business rather than just consolidating the administrative burden into them.

9

Chapter 1

Building from Scratch

Decision by Committee Sucks We had just concluded a recruitment process for a senior software engineer. The process involved a number of team members who were involved in the various assessment and interview stages. We came together for a quick debrief after compiling our recommendations individually, only to find a rough split across the team. Four people had suggested a yes to hire, and two people had suggested no. We had two attempts at this debrief to come to a decision with the manager clearly looking for a group decision. In the end, the manager decided that as the group couldn’t come to a single decision, that it was a “no” decision for that candidate. This same process happened for a number of candidates. When the recommendations were unanimous, we proceeded quickly. But when it was not unanimous, we defaulted to no. Now, there’s no saying whether each decision was right or wrong but that’s not the point. The point is that a pattern existed of us delegating decision-making authority to a large group of people and setting the expectation for those people that they were operating as a committee. It was probably more like a jury in practice, but let’s keep going with the committee analogy. That decision-making process within the committee was poorly executed and the result was a slow and inefficient process and high risk of a poor-quality decision too. There are several reasons for this: •

10

Recommendations were coming from people involved throughout different stages of a recruitment process. Those who were completing the technical assessment were evaluating on a different set of criteria to those completing the pair programming assessment, and those doing the cultural interview. It meant the recommendations were ultimately apples and oranges, each grounded in different explicit and implicit criteria.

Chapter 1

Building from Scratch

•

We did not distinguish between feedback and recommendations. We sought recommendations from the team when what we actually needed was input to the recommendation. This set poor expectations for the team too, who initially responded positively to the opportunity to play a bigger role in hiring efforts, as they were often investing huge amounts of time into a recruitment process and seeing very few people emerge successful from it.

•

We made a poor assumption that candidates needed to tick every box. If a candidate performed really well in all but one part of the recruitment process, the team member who was in that one part of the process is only looking through a very narrow window into how that candidate may perform in the role.

•

There was a bit too much desire to please and agree from me, and likely the manager too, so if the committee was split, we defaulted to the more conservative option and encouraged the team that next time would be different.

This example is rooted in a recruitment process, but very similar behaviors happen throughout all sorts of team routines too. Picture the leadership team who struggle to agree a way forward because some people aren’t on board. We idealize consensus and agreement which doesn’t lead to high-quality decisions. Or fast ones. We made a lot of changes to our recruitment process to focus on how we were making decisions. Most of these changes apply to broader forums too:

11

Chapter 1

Building from Scratch

•

Clarity: Identify the decision-maker who is solely responsible for making the call. They should be the person who is accountable for the result of that decision.

•

Expectations: Set expectations with other team members for what role they will play. In the recruitment debriefs, we let team members know the debrief will be to share their notes, observations, examples, and any concerns relating to the part of the process they were involved in.

•

Partnership: Establish the People team as a partner to that decision, helping the decision-maker consider the feedback and input and prioritizing what is important.

•

Get it done: Make the damn decision! As you will have just read, done trumps perfect and all decisions carry risk. So make yourself comfortable with that risk and make a call. We won’t get them all correct, but it’s still better than indecision.

•

Communication: Communicate the why behind the decision and genuinely recognize the input, whether it supports the decision or not.

Beware the Magpies If you’re unfamiliar with magpies, they are a beautiful black and white bird with a reputation that precedes them. Magpies are known for their attraction to shiny objects. Whether that’s actually true or not, and how magpies actually perceive shiny objects, is beyond my knowledge. When I was growing up in Australia, we would ride our bikes up and down

12

Chapter 1

Building from Scratch

the street wearing brightly colored and sparkled helmets which would encourage magpies to swoop and attack us. Seems pretty stupid in hindsight. Many years ago in the early days of my HR career I had a colleague who described me as a magpie. I suspect it was meant as a subtle insult but it’s something that has stuck with me for a while, both in terms of the underlying message but also reflective of my behavior at the time. I was an absolute sucker for opening up a magazine or LinkedIn, reading about something I thought was really cool, and coming to work the next day and wanting to implement it. A sales team with no commission structure? LET’S DO IT! An entire company without reporting lines and job titles? LOVE IT! An entire company where you get to set your manager’s, and the CEO’s, pay? WHERE DO I SIGN UP?! It might come as no surprise that once I joined my first startup, my magpie personality started to reemerge. Faced with an environment that was all about moving at pace, iterating, experimenting, and innovating, my ears would prick up at any talk of the next revolutionary working practice or something I heard at a conference or read online. This time around, however, I was a bit more aware of what was happening and needed to find a way to harness the magpie spirit without forgetting there’s a context and thoughtfulness needed to make something work in that specific startup. I started to build mental lists of what was happening within the industry and the major shifts facing employers – from the rise of flat operating structures to increased benefit flexibility, to really innovative learning and performance solutions. I was consciously avoiding copying and pasting the new, shiny ideas I was seeing elsewhere and starting to think about what I could learn from those ideas and in what context there would be value to rethinking our current approach. I remember in the early days of a startup we were discussing learning cultures and how to really ignite the curiosity and passion for learning within the team. We had budgeted for training but the budget was rarely

13

Chapter 1

Building from Scratch

used. There were also some conferences and workshops we paid for but only for a very small number of the team who had put their hand up and really pushed for it. This was also around the same time as we saw the emergence of payments platforms that let you distribute budgets for flexible benefits. Bingo! We put in place a learning budget that allowed people to use virtual payment cards to self-service their own learning resources. We removed the perceived barrier around needing to ask for permission by removing all approvals and trusting that people will do the right thing (98% of people did), and we integrated with a learning Slack channel to automatically share what everybody was investing their budget in. This was also a team accountability step – if you bought an iPhone with your learning budget it would be posted on Slack for everyone to see. What transpired after this was pretty special. People started making recommendations to each other on useful learning resources. Small teams started forming to participate in group workshops and conferences together. We set up a company library of resources and playlists to help folks interested in learning new skills. And it operated itself, with almost no involvement from the People team. Beware the magpies. There are a lot of us, and left unchecked, we are directing energy into things that are not driving genuine value in a startup, or any company for that matter. Help us build context for initiatives and steer us back on course if the excitability is not grounded in what’s actually important in the company.

 our People Strategy Is Your Y Business Strategy I once worked in a team where we presented the People strategy to the company before the business plan was finalized. Which in hindsight feels a bit odd. Where did the people strategy come from exactly? How did we

14

Chapter 1

Building from Scratch

manage to identify where to focus our time, and communicate why that was the case, when we didn’t yet have a broader business plan to guide the direction of the company? While it took a few detours through teams like that one, I’ve come to learn that the people strategy is an enabler of the business strategy rather than a stand-alone strategy itself. There isn’t a single pillar of a startup’s strategy, or a single team within a startup, that doesn’t have a significant component of their success directly related to people. Be it ramping up customer success teams to deliver an exceptional, global experience for customers. Or maturing a reward framework to drive a more predictable cost curve. Or planning the growth forecast for investors to ensure there is adequate, ramped sales capacity to deliver revenue goals. I no longer invest huge portions of my time, even as a Chief People Officer, designing a long-term people strategy. Instead, time is invested in getting under the skin of all parts of the company, understanding the challenges and performance drivers, and considering how people solutions will drive the success in that area. And then we make it happen. This reversal of approach does not dilute the people-first approach in any sense, but rather offers significantly more buy-in around the work that needs to happen when it directly impacts the performance of the company.

Summary •

Ground your decision-making in data and make it transparent. The goal is not to please people. Good decisions sometimes piss people off.

•

Avoid short-term temptations for bespoke employment terms. You’ll build a people debt that comes back to bite you in the ass once you grow.

15

Chapter 1

16

Building from Scratch

•

Perfect work rarely delivers materially more value than good work in a startup, so get it done and trust your ability to iterate it over time.

•

Build automation and self-service into as many administrative processes as possible to delay your need to hire and reduce administrative burden.

•

Be clear on how decisions are made and what inputs are needed. Decision by committee is neither fast nor does it result in a higher-quality decision.

•

Every initiative you work on must be aligned to the priorities of the company. Work your way inside out to understand what people solutions will solve challenges and enable success in each team. And beware magpies!

CHAPTER 2

Leadership In the last chapter, we covered the myth that is the blank canvas we’re building from and the paint that already exists on that canvas. Arguably the biggest source of paint and the state of the business you’ve joined will be in the leaders that are already in place. So in this chapter, I want to get under the skin of startup leadership which, unsurprisingly, appears frequently in my mental notes. I have several shelves of leadership books in my home. Most of them have imparted nuggets of wisdom or know-how into my brain, yet despite having read so many leadership books, I still can’t say with any confidence they actually prepared me at all for the realities of leadership positions. The recognition that leadership is not a position is well understood, but for the purpose of this chapter when I use the word leaders, I am referring to those who are leading a team. An investment in leadership is hard work, but well worth the return. It might take a combination of developing existing leaders, promoting from within and hiring externally. In many small companies, even before people leaders are in place, they are seen as a hierarchy and structure, regardless of the person and their style. Being clear on the “why” helps as does casting a vision forward to how the company will grow over time. Most importantly, it’s a recognition that leaders cast a shadow that runs deep into a company, especially a startup, so it’s vital that shadow is having the best possible impact on the team.

© Patrick Caldwell 2023 P. Caldwell, People Ops, https://doi.org/10.1007/978-1-4842-9819-0_2

17

Chapter 2

Leadership

There are several parts to this chapter that cut across the People remit. So for that reason, I’ve kept the focus on some of the key leadership challenges that exist in a startup, kicking off with my three red flags. These red flags are three things that are constantly sitting on my radar from the moment I start with a company. When you get these right, the value is immeasurable. When you screw it up, like I have a few times, the damage takes a long time to recover from.

Red Flag 1: Lack of Leadership Before you immediately think this is rubbish and startups do not need more leaders, it’s certainly not lost on me that startups need a disproportionate number of driven and capable individual contributors compared to leaders. But let’s cast back to when a startup is 20 or so people. In the initial, scrappy phases, the founder(s) were likely the leader for everyone in the company. Even at 20 people it’s quite normal for most people to be reporting to a founder, or at best there might have been an early leadership hire into a sales, operations, or technical team. As the team grows to 50 or enters the journey after Series A funding, the roles and expectations of leaders fundamentally change. There is now a need for leadership beyond the founder(s) who are also transitioning into operational roles as C-level or senior team members. During this phase, spans of control often balloon. It’s not uncommon for one or many founders to have teams that are 10, 15, sometimes 20 people strong. Temporarily you can cope with a large span of control before you usually see symptoms that it’s time to outgrow that foundercentral leadership structure. Your team will start to demand functional expertise and mentorship. Founders will start to end up with remits that are far too wide and result in ineffective leadership or burnout. Investors will start to look for a transition away from founder-led success to

18

Chapter 2

Leadership

repeatable, consistent success. All of these symptoms point to the need to make a deliberate and thoughtful investment in a leadership structure that can scale the company through the next stage of growth. There’s no exact playbook for this, but if you’re finding yourself in this sort of environment, here are a few tips to start: •

Start at the top: Work with the founders and members of the Board to build clarity on the substantive role each founder will play. By substantive role, I mean the one that’s not called founder. That is a large, heavy, and very important hat to wear, but the founder will also likely be the CEO, CRO, CTO, or some other role. That’s the one I’m referring to. Their substantive role is vital as the company moves from being founder-led to a sustainable business engine.

•

Accountability: Each role on the leadership team should offer a single point of accountability for results in their area. If you have a leadership team where several members all own a revenue goal or the product road map, you’re setting yourself up for conflict, unnecessary meetings and bureaucracy, and a lot of confusion within the team.

•

Completeness: Collectively, the leadership team should offer completeness. This isn’t to suggest you need every functional leadership role immediately on the leadership team, but rather if you consider your challenges over the next 12 months, are there any glaring holes? What areas of your performance and strategy sit between teams or across teams? Is it clear who on the leadership team will own these areas?

19

Chapter 2

Leadership

•

Leveling: Be conscious of titling as the company grows. If you’re 20 people with 8 customers, is the leadership need you’re really describing that of a Chief Customer Officer, or is the best skillset at the Head, Manager, or Lead level. Unless you’re using titles to get you in the room with prospects, strongly consider hiring at the level that role needs in the short and medium term and work hard to help that person grow into the next level leader you might need down the road.

•

Fractional leaders: Consider fractional executive leadership if a full-time role is either out of the budget or premature in terms of workload. A fractional exec, particularly in key growth areas like Finance, GTM, and People, offers a much more practical way to ensure you’re focusing on the right things at the right time.

•

Relevance to now: Consider the job description of every leadership role in the context of taking you from point A, where you currently are, to point B, where you want to be in the next 12–18 months. Most leaders have a sweet spot in a company’s growth journey so be very mindful of hiring in leaders who are exceptional at point D and point E when you’re nowhere near that yet. You’re setting yourself up for difficult conversations about 6–9 months into their tenure.

Make sure you have a passionate, committed, and capable people leadership team before, and as you grow. It's rough ground without it.

20

Chapter 2

Leadership

Red Flag 2: The Wrong Leaders It’s time to call a spade a spade. There are times throughout your growth journey where you will have people in leadership roles who do not embody the leadership behaviors, culture, and performance you’re trying to achieve. You might be trying to strengthen accountability within your team while your sales leader is overstating pipeline and close dates. Or you’ve committed to becoming a more transparent company and your operations leader is not communicating what they’re working on or providing important data to others who rely on that to do their roles. Or perhaps you’re taking on your team’s feedback in an engagement survey around inclusion and having their voice heard and your product leader continuously talks over others or shuts down any idea that isn’t their idea. If you’re recognizing this sort of misalignment within your leadership team, know that you’re not alone. It happens all the time. In most cases, the reasoning behind the misalignment is quite innocent. Leaders have built styles, preferences, and behaviors over their career and in some environments they may be incredibly effective and in other environments they can do a lot of damage. In a small number of instances, the reasoning is less innocent and those leaders have more devious traits. Leaders cast a wide and impactful shadow on those around them. Poor behaviors infect teams and, if not managed, can influence the culture of those teams over time which becomes more difficult to unwind. Act early. Do not trust that the problem will fix itself. It won’t and great talent are rightly impatient when it comes to whether they should stay or go if they are experiencing the symptoms of a poor leader. Once a behavior is called out, you owe it to the leader to help them change the behavior swiftly and consistently. If they aren’t coachable or take the matter seriously, they need to go. The damage a poor leader can do in a small company is profound and it shouldn’t take great people leaving for it to be dealt with.

21

Chapter 2

Leadership

Red Flag 3: Accidental Leaders You’re a software engineer and an early employee at a startup. Initially, your days are spent coding and building your product. The road map of work, combined with greater support requirements and some projects from customers, starts to outnumber you, so you hire someone into your team. Then another person. And another. Then a few more. All of a sudden, you’re now spending a disproportionate amount of your time managing people and processes and not what you joined the startup to do. You’re not complaining about it, but it’s not why you get out of bed on a Monday morning and you might feel you owe it to the startup or the founder to just keep going. I call this accidental leadership. Through a long line of small changes at a company, it’s where a talented individual contributor accidentally ends up managing a team in order to keep up with the pace and delivery of work at the startup. They become an accidental leader. Sometimes it happens in months and sometimes in years, but to no fault of their own they’re now in a leadership role by accident. It happens more often than we might think. If a leader’s description of their perfect role at the company, and what brings them energy and fulfillment, is not a people leadership position, you need to act. I’m not suggesting you let them go but rather you need to find a role that better aligns their strengths and interests with what you need in your company, and appoint someone into the leadership position who really wants to do that. Accidental leaders can go unnoticed for years. It’s usually a combination of factors that let it go unnoticed too. Fear of putting their hand up and suggesting they’d rather be doing something else. A belief that, over time, they’ll learn to enjoy their new role. Feelings of commitment and loyalty to the founder or person who gave them the opportunity. Or they’ve just been so in the weeds of the business that they never really stopped being an individual contributor and they ignore or avoid their role as a leader. 22

Chapter 2

Leadership

Accidental leaders can be inhibitors to growth, but seldom do they carry the same risk or worry as a lack of leaders or the wrong leaders. But they are a reality of a startup and it’s important to not let them go unnoticed and ensure you’re having open and candid conversations with them to create safety for the possibility that they might like to step out of that role and do something else in the business. And that is the key for accidental leaders. You don’t want to lose them and they likely don’t want to leave, but you might need to reconsider the role that will let them contribute their fullest and allow them to explore their passion again.

 ot Everyone Wants to, or Should, N Be a Leader We need to unlearn this idea that in order to develop your career, you need to move into leadership. I cannot think of a more painstaking role in a startup than leading a large team if your heart's not in it. One of my personal lessons was assuming that leadership development was just for leaders and future leaders, rather than it being about building the skills and knowledge relating to leadership. I was reminded of this by a senior individual contributor who had been in a leadership position before, hated it, but was still passionate about building his skillset around leadership knowing it was transferable into many parts of his role. It feels like a rookie mistake from me in hindsight, but based on how many leadership programs I still see that are only designed for those who lead teams, I suspect it’s a pretty common rookie mistake. There are two things I now try and make sure are crystal clear from a leadership progression and development perspective: 1. Progression: Progression frameworks should have a fork in them, where some people progress down the path of leading teams and others progress through

23

Chapter 2

Leadership

more senior individual contributor roles helping to shape strategy, make complex decisions, and take on more senior responsibility. If your progression framework is a single line, those in your team who do not want to be a leader will hit a plateau and likely look for that next experience outside of your company. 2. Development: Leadership development should cater for those in leadership positions and those who are not. There is a safety you will inevitably try and create for those in leadership positions to develop their skills within an environment of peers, so some delineation here is likely important. But those skills you’re trying to develop around resilience, coaching, motivation, feedback, communication, and change are beneficial for lots of people to allow them to progress and arm them to do their role to their fullest potential.

The Psychological Safety of Leaders Leading teams is hard. Reading books (even this one), taking classes, listening to podcasts, and going to conferences all tickle that curiosity and might give you a few tips, but nothing actually prepares you for what it’s like. And once you do experience the highs and lows that come with leadership positions, it can often feel like a lonely place. If you’re reading this right now and feeling like a bit of an imposter, or that you’re not cut out for leadership, or you’re looking around and seeing others who are seemingly more confident and comfortable in their leadership roles, know that you’re not alone. I see you.

24

Chapter 2

Leadership

I’ve been working with, or part of, leadership teams for the last decade. I’ve worked alongside leaders who have had moments where they feel they have conquered a mountain, and moments where they feel completely inadequate. I, too, have felt that way. What is missing from the leadership rhetoric, particularly in growing startups, is the expectation placed upon us to be and act a certain way. To have time for everybody but still have time for ourselves. To be thinking strategically and making long-term decisions, but still be close to the day-to-day work. To be poised, calm, and positive in the face of adversity, but not so much as to be inauthentic. To express vulnerability, but not so much to be seen as weak or incapable. The weight of this expectation can be crippling and I’m convinced that if more people knew how it actually felt being in a leadership position, it might not appear so regularly in career development discussions. This might sound pessimistic, but the rose-tinted facade placed over moving into leadership positions and how great it is to make decisions and earn more money results in nothing more than a leadership honeymoon before the reality of expectation sets in. Some leaders in startups navigate this really well and find balance between the expectation and fulfillment. Other leaders do not, and end up feeling pretty miserable or in some cases doing a lot of damage to the startup cultures they’re operating in. It took me a few years to really feel comfortable, or at least less uncomfortable, in leadership positions. I had to navigate feelings of inadequacy and also show resilience for when things went wrong, which was often. What helped me was deeper than just a great manager and a network of people in similar roles. I leaned heavily, and still do, on a small and trusted set of people who I feel 100% comfortable being myself and having a no-bullshit conversation around what was happening. For you, it might be a mentor, therapist, former colleague, or significant other. I found the safety and candor that existed in these relationships allowed me to understand more about the gap between the leader I was (and am) and the leader I want to be. It’s also helped me realize that I like

25

Chapter 2

Leadership

balance in the role between operational building and leading teams which is why I try and make sure I’m the first People boots on the ground in a startup where I find that balance over the next few years of growth is spot on.

If Difficult Conversations Don’t Affect You, You Shouldn’t Be Having Them Earlier in my career, I found myself a regular member of project teams who were put together to enact restructures and reduction in force. There were always a very small number of people satisfied by the prospect of receiving a severance package as they neared retirement or were considering work elsewhere anyway. For the most part, though, the people on the other side of a conversation with me and their manager were neither expecting it, nor did they want to hear the news. Randy, who had a stay-at-home wife and small child and was now wondering how to make ends meet. Alison, who relocated internationally for the role and would no longer have a working visa to remain in the country. Ashley, who recently took out a mortgage and now faces severe financial pressures. Each of these folks had their lives uprooted because of things well outside of their control and by people who, at best, could only empathize with how that felt rather than actually understand it. During one particular restructure, I was sitting in a meeting room with our project lead. We were discussing some of the conversations that needed to happen and my emotions started bubbling to a point where I couldn’t suppress them. I was feeling a lot of things but one in particular I remember vividly and, even to this day, the feeling hasn’t completely subsided. I felt guilty. That it was my fault that so many of my colleagues were now out of work. That the pain they experienced hearing that their role was going to be removed from the company, and the aftermath of this, was my wrongdoing.

26

Chapter 2

Leadership

It was the first time in my career I’d become quite emotional and, for me at the time, it was a signal that I was no longer the right person for this sort of work. I wasn’t resigning, but I wanted out of the restructuring and all of the difficult conversations that came with that. I was a blubbering mess in a meeting room with the project lead, making my case for why they needed someone more experienced and more resilient than me to take over. I was clearly not fit for the job.

“If you want out, I’ll make it happen. But your empathy is a strength, not a weakness. If difficult conversations don’t affect you, you shouldn’t be having them.” I don’t think they intended those words to have such a profound effect on me. It’s been years since that conversation, but it’s something that I find myself reflecting on and revisiting often, especially in startups where the environment is more volatile and difficult conversations more prevalent. We’re now accustomed in startups to hearing stories of being laid off by a group video call, an email to a personal account, or even when an access card doesn’t work at an office. Behind the scenes, the argument leaders will be making is the need to execute these changes with pace and efficiency. To make the decision, move onward and keep building toward the startup vision. Here’s the thing. Outside of a small group of stakeholders, this replacing of difficult conversations with impersonal behaviors is not seen as efficiency, but rather cowardice. We have to unlearn that it’s acceptable to avoid difficult conversations and remove humanity from difficult decisions. We owe it to our team and those around us to experience those difficult conversations fully. If they make you feel like crap, good. That’s what it means to be human and make difficult decisions relating to people. If you’ve just let someone go or given some really tough feedback, you’re likely only feeling a fraction of the difficult emotions that the other person is feeling. And if you don’t feel anything when making those decisions, maybe you’re not the right person to be making them after all. 27

Chapter 2

Leadership

 ometimes to Show You Care, You Need S to Show Your Teeth I wrote these words down within minutes of a leader saying them. We were working together to deal with a fascinating challenge around performance and attitude. A member of the team found fault in everyone else’s work except their own. They gave feedback to others freely and without second thought and regardless of the impact it had, but when faced with feedback they closed up, externalized, and disagreed. When assigned work or a project, it was met with support if it involved doing things they enjoyed doing, and was met with avoidance or pushback when it didn’t. The reason this was fascinating was because of the polarity of responses. Their work was not of poor quality. Quite the opposite in fact. But the impact they were having on the team environment was terrible, and they had quickly built a reputation both within their team and across teams as being a bit of a brilliant jerk. Other members of the team didn’t want to talk to them, let alone work with them. And so the manager decided to have a conversation with them and provide them some feedback about the impact of their behaviors and to discuss some ways they could start to work on that together. Shortly after, the team member pulled me aside with quite a dramatic monologue about the inappropriateness of their manager, that they wanted the manager to face disciplinary action, and that they wanted to be moved into another team. There were also some pretty wild accusations and assumptions about the manager’s background and their abilities. The manager never knew the details of what the team member shared with me, but they were aware that they were “reporting this to the People team.” In the days ahead, I learned of another conversation the manager had with the team member. This time, they took a different approach. The manager shared clear examples of what was happening, made it crystal clear to the team member what was expected of them, expressed

28

Chapter 2

Leadership

disappointment in how things had progressed, and then laid down clear consequences for their employment if immediate change didn’t happen. The team member was asked to take the rest of the day off to reflect on the conversation, and they could either return the next day committed to working in a new way or they could consider this a formal employment matter. In my chat with the manager, they said it was an overdue conversation that they wished they had done earlier but didn’t want it to be perceived as not believing the team member could get to where they needed to be. But to show you care, sometimes you need to show your teeth. This was not a case of rain one day and sunshine the next. There were challenging moments for months, but the signs of improvement were there and slowly the team member started to get out of their own way and realize the impact they could have with a more constructive way of working. And it made me appreciate the link from the manager between having a truly candid and open conversation with a deep care for getting the most out of a team member. By definition, leadership cuts across all areas of the people and culture remit so this chapter touches on several of the different milestones and stages of the people experience. In the next chapter, we’ll take a more detailed step into Culture, which in the startup space is about as fluid as it gets.

Summary •

Identify areas of the company where there is a lack of leadership capability and accountability, where the wrong leadership behaviors are playing out, or where accidental leaders need safety to move out of their roles.

29

Chapter 2

30

Leadership

•

Leadership is hard and not for everyone. Embed into progression and development programs the option to pursue people and non-people leadership roles. If you are in a people leadership role, find that psychologically safe space to share your highs and lows.

•

We can’t, and shouldn’t, avoid difficult conversations. It’s human for us to be affected by them and that is not a weakness. Sometimes those difficult conversations require us to change tune and show our teeth to get the best outcome for someone.

CHAPTER 3

Culture The link between leadership and culture is undeniable, so it is only logical that after exploring leadership red flags, safety, and capability in the previous chapter, this next chapter will explore the flow-on effects to the shadow that leaders cast. This chapter is all about culture and, as you will see by the first lesson, it starts with having a shared understanding of what that means. Once we have that, I’ll share with you some of my most impactful mental notes from startups around autonomy, process, values, layoffs, and of course, the great culture fit vs. culture contribution debate.

 ulture Is Not Free Beer, Fruit, and a  C PlayStation If you’ve ever visited a career page for a startup and been hit with images of people drinking, sitting on bean bags, and playing table tennis, you’re not alone. After all, what better way to highlight how fun a work environment is than to promote images of people doing anything other than work. Combine this with things like free beer and PlayStation as benefits in the job description, and who wouldn’t want to join, right? There is nothing wrong with this stuff because some people enjoy it. But it’s not your culture. In the world of startups, there’s a history of relying on beer and table tennis as symbols of coolness, culture, and “how we put people first!.” And it worked for a while. But most people have clued on to the vanity and are demanding a lot more transparency around actual culture.

© Patrick Caldwell 2023 P. Caldwell, People Ops, https://doi.org/10.1007/978-1-4842-9819-0_3

31

Chapter 3

Culture

Culture is deep and it pays to get under the skin of a company and really understand how it works. At its simplest level, culture is just a way to describe how stuff happens at a company. How do people communicate? How are decisions made? What happens when shit hits the fan? Does everyone rally together or do people start pointing fingers or working in silos? It may be very possible that several cultures exist within your company. It might be driven by teams. Or the location of your people. Or even the tenure of your people (think “old guard”). Culture is inherently fluid both in how people can influence it and how people perceive it. A small company with little to no hierarchy and decentralized decision-making may be described as being both fast-paced and autonomous by one person and chaotic and stressful by another. Both are valid perceptions of culture that we need to own and work on rather than wasting time trying to convince anyone that table tennis is culture. Culture matters to people. It’s why many join a company, and it’s usually what drives people away. So much so that many job candidates are also suspicious if things seem too good to be true. Because they probably are. If people don’t feel empowered by leaders, have tension and barriers between teams, and don’t feel a sense of accomplishment in their work, the free beer and fruit basket isn’t going to keep them around very long. The best thing we can do is be authentic and transparent around the actual culture of our companies. Highlight the great stuff that our people tell us is meaningful. And then highlight the culture challenges and how we’re approaching them. No workplace is perfect and, in my experience, people value honesty, transparency, and commitment over vain attempts to define culture by what’s in the fridge.

Culture Contribution or Culture Fit When you’re small enough to count everyone on your fingers, your culture is likely more fluid than you think. Sure, you might have extremely strong traits and behaviors from existing team members that anchor the culture. 32

Chapter 3

Culture

But if you’re planning to double or triple in size, your culture is going to change. The question is not whether you can stop the change, but rather whether you’re up for defining and managing that change purposefully and in a way that allows your business to keep both the special sauce that makes you “you,” and evolve in a thoughtful and deliberate way. We’ve been throwing around the term “culture fit” for decades. Sometimes it’s for exactly what I’ve described earlier around evolving a deliberate culture without losing its special sauce. Sometimes it’s for a very different purpose that allows bias to play out freely and, as a result and perhaps unfairly, it’s increasingly seen as something we should be wary of. You’ve probably seen the rhetoric in more recent times around culture add and culture contribution rather than culture fit. Culture fit never stopped being relevant. It was just bastardized over time as a poor excuse for letting our similarity biases play out and hiring in the shadows of existing team members. It’s the equivalent of me building a business, hiring a bunch of folks who look like me, talk like me, think like me, and act like me, and then calling it culture fit. We also see it rear its head throughout recruitment processes as the catch-all reason why someone doesn’t get a job. Candidates spending three, four, or five hours in interviews and being told they aren’t progressing with no more detailed feedback from a hiring manager than not being a culture fit. It’s no wonder that it’s become tarnished. But those examples are simply bad leadership behaviors playing out, not an invalidation of the concept of culture fit. I remain a huge advocate of what culture fit can and should be. Checking the alignment of values and traits of new team members to the company. Ensuring that someone joining or even moving to a new role internally is set up for success and can thrive within that operating environment. If you’re hiring into a 50-person startup to establish the first customer success function, you’ll likely be looking for someone who gets their kicks from creating and building order within unstructured and ambiguous environments. Someone who is comfortable building processes and new ways of working where they likely don’t exist before. That’s a form of culture fit. 33

Chapter 3

Culture

Similarly, if that startup values transparency and there are rituals around transparent learnings, results, successes, and failures, you should be looking for a strong culture fit within interviews around how they have or would demonstrate transparency within their role. Without that culture fit, you’re likely putting someone in a very confronting situation once they start if they aren’t already aligned with your values. Let’s talk about culture add. The rebirth of culture fit to reflect that the last thing we want to be doing is hiring a bunch of mini-me team members. Unsurprisingly, I’m a huge advocate of this too and I don’t believe it’s mutually exclusive with culture fit. Keeping with the customer success example, I remember hiring for a startup’s first customer success leader. The startup already had some bits and pieces in place, but following some team changes and a record-breaking year of new customers, we were in need of a CS leader to wrap their arms around the entire remit and build out an effective and scalable function. The leader we hired was a resounding “yes” at every stage of the recruitment process, and if we were explicitly scoring on culture fit and culture add as part of it, they would have scored highly on both. They demonstrated a strong alignment with our company values and no shortage of examples from their experience to back this up. They also shared, in detail, the specific challenges and solutions they’d faced coming into startups at a similar stage where there was very little in place other than high expectations and demands. We were confident in their ability to excel within our culture and how we operated as a startup. Culture fit. What made us excited though wasn’t this alignment and fit with the startup. It was what they would contribute to our ways of working, values, culture, team, and growth that didn’t already exist within the team. Experience and perspective from incredibly diverse industries. Countless examples of innovative thinking and breaking traditional rules (some we believed in too) to get impressive results. At each interview stage, we left feeling like our thinking and perspective had been stretched. If we hired

34

Chapter 3

Culture

this CS leader, we’d be pushed in an uncomfortable but necessary way in order to build a customer experience that was both incredible and scalable. Culture add. There should never have been a debate around whether culture fit or culture add was the goal, because it’s not an “either or” scenario. When you’re building your team and iterating your culture in a deliberate way, you’re looking for both. A fit within your values, norms, and the stuff that makes you special to make sure someone can be successful in that environment. And an addition and contribution to your culture that brings breadth to your perspective and, hopefully, even makes you feel a wee bit uncomfortable.

What Does Autonomy Look Like for You? “Why do you want to join our business?” “I really want to work for a startup.” “Why’s that?” “I’m looking for more autonomy in my role.” “What does autonomy look like for you?” It’s a common conversation that most startup recruiters will relate to. The candidate who comes out of a large, corporate organization and wants to experience the roller coaster that is a startup environment. During the recruitment process, there’s a word that always pricks my ears up and something that has become synonymous with startups. Autonomy. Autonomy in the workplace has fascinated me for years. We read books about why it’s a must-have in order to achieve engagement from your team. And it’s something that so many people seemingly are striving for in the workplace too. But something has always made me feel a tad uneasy about autonomy, which is that for each person what autonomy means

35

Chapter 3

Culture

can vary quite significantly, and that it’s not automatic that people thrive with autonomy. So I’m always curious when a candidate in a recruitment process talks about autonomy, what do they actually mean. What does autonomy look like for you?

“I want to make decisions.” “I want to have my voice heard and a say in how things are done.” “My manager is a micromanager and I don’t like that.” “I want more flexibility in how and when I do my work.” “Things feel so bureaucratic here and I just want to GSD.” Every one of these among dozens of different responses to what autonomy looks like for candidates, ranging from leadership roles, developers, salespeople, graduates, and even the People team. And every one of these touches on interesting facets of culture and how people perceive autonomy. Autonomy in a startup is a unique thing. The level of responsibility and proactiveness needed can thrill some people, and shock others. Clarity is not a given, nor is direction sometimes, so autonomy can be as extreme as complete self-ownership and governing of our roles and their outputs especially in the early days. In terms of finding culture fit and alignment between how someone best contributes and the culture of the company, I can think of very few more important things to discuss candidly and transparently than that of autonomy. They want to make decisions? What sort of decisions? Can they share more about a time when they wanted to make a decision but couldn’t, and what happened? Are there situations where someone else making a decision would be received poorly by them? What’s their thinking process behind important decisions – do they consult, engage, and inform?

36

Chapter 3

Culture

Your manager is a micromanager? What support and behaviors do you look for from a manager in order to do your best work? What level of autonomy feels right for you in this sort of role? What behaviors does your manager display that make you feel micromanaged? I’ll almost always ask that last question when micromanagement is raised as you might be surprised how often the simple action of being assigned a project or asked for a one-off status update is seen as micromanagement. While the general feeling of having more control and ownership of what you’re doing fits firmly within autonomy, it’s such a critical part of culture fit that it’s worth investing a bit of extra time to discuss and make sure you’re aligned. Otherwise, if they’re looking for a highly autonomous role where they decide what they work on and when, and that’s not the level of autonomy you have within your company, you’re setting them up to walk through a revolving door.

Process: The Enemy or the Hero? I LOVE a good process. The simple art of determining the effective steps in order for something to be completed consistently, repeatedly, at pace, and helping everyone else has clarity at the same time. Right? Right?! At least it should be. If you’ve ever joined a large company, you’ll be met with established, documented processes before you even start on your first day. Preboarding, onboarding, compliance training, policy documents, checklists, and that’s before you’ve even started doing any work. And once your feet are under the table, you’ll have operating processes, SLAs, workflow maps, RACI frameworks, and all of the other process joys designed to achieve what we described earlier. If you’re joining a startup or very small company on the other hand, you’re going to be met with very little process and structure. They’ll likely have some compliance steps along the way but otherwise they’re doing 37

Chapter 3

Culture

well if they have any sort of onboarding or operational processes if they’re still in a scrappy phase. Process, implemented at the right point in time and with the right conditions, can be hugely effective in helping a startup mature how they operate from scrappiness to repeatable and consistent success. We see it in sales teams when playbooks, methodologies, and territories all start to emerge. We see it in product teams when road maps are formed, sprint cycles are put in place, and quality assurance are embedded into how the team operates. And we see it in People teams when hiring and onboarding become a priority, if performance and reward need linking and even for simple things like leave and payroll. There is, unfortunately, a dark side to process. When we prematurely introduce it, or we implement a process that is not reflective of where the company is at in their journey. It’s well intended but dangerous overkill and runs a real risk of both hampering pace and progress and disengaging early-stage employees who thrive in the scrappy and unstructured environment. There is always a time and place for it, and we need to make sure we don’t make process the enemy to our progress. One of the most common process pitfalls happens around approvals. As the company grows, there comes a need for more mature governance practices. Typically, you want approvals to sit at the lowest possible levels in order to keep processes effective but also demonstrate enough governance to avoid risk. Take something like new vendors, something which all startups will eventually have a process in place and something that touches a lot of different teams. Now picture a 100-person startup with this uncomfortably common process. An engineer is working on implementing a new alerting technology and has identified a vendor to deliver this. The engineer needs to submit a proposal to their manager, then to their two-up manager, and then to the Finance team. The Finance team then seeks endorsement from the founder who still wants to be across all new spend decisions. Once the spend is approved, the engineer needs to get IT to approve the implementation, Legal to approve the contract terms, Finance to again 38

Chapter 3

Culture

approve payment terms. And if this process happens for every new vendor, on spend over a low threshold, and with a bunch of internal documents and procedures to match over email, you’re requiring your engineer to spend days of time preparing and trying to get everyone to approve it before they’ve even started implementing a new alert system. If that engineer has been around the company for a little while too, they’ll remember vividly how easy it used to be, “in the good old days” when they and their manager could pump out all of that work for a $5k contract in an hour or two and make it live by end of the week. While process is important at times, overusing it in growthstage companies starts to chip away at the pace and agility that likely differentiate you from bigger players in the market. Things will slow down and become more structured at some point, so best not to force it prematurely.

 ut Only When Is Absolutely C Necessary to Survive I used to be part of a business where restructuring happened so often to cut costs that the HR team started to be viewed as redundancy squads. It’s really hard to achieve anything meaningful in your people strategy when there’s an underlying sense of “Am I next?,” as even once a restructure was complete those who remained remain unsettled without the friends and colleagues that were once part of their team, and wondering not if another restructure will happen, but when. In startups, we face a similar cycle sometimes when a company’s revenue doesn’t keep up with its spend, or when there’s pressure from stakeholders to reduce the burn rate if the startup isn’t profitable yet. It pains me to hear of stories where teams are ripped up while executive bonuses are still paid, folks are still traveling business class to conferences, consultants and vendors are being paid tens of thousands of dollars, and 39

Chapter 3

Culture

no one is really sure what value comes from it, and yet in order to “position the business toward sustainable growth,” there needs to be a reduction in workforce – which, while we’re taking aim at this, disproportionately affects people and talent, marketing, operations, and customer success teams where apparently they are only valued when growing. OK, that felt good to get off my chest! There are times when reducing the size of the team is absolutely necessary, and I get that. But it should never be the first lever you pull. The cultural damage it causes along with the slow rebuilding needed if things pick up are both huge deterrents to leaders and People teams. It should be the last lever you pull, and done in a way that preserves the values of the company and nurtures both those who are leaving and those who remain. Reducing the size of the team is an expensive exercise, both in terms of the financial cost to do it properly and the emotional and well-being cost that will drag for months or years after it happens. If you’re faced with a challenging commercial environment and under pressure to reduce costs, here are a few things I’ve learned from having been through this far too many times.

E xhaust Every Other Option First to Bring Spend Down I cannot restate this enough. Go line by line through where you’re spending money in the last six months and challenge everything. While some of these numbers won’t look big, if the spend is not critical to what you need to do in the next 12 months, set it aside to review options to reduce or remove the spend. Things like travel, entertainment, software, consultancy, facilities, and services are all great places to start and you only need a handful of cost-saving opportunities in these areas to be equivalent to headcount costs. Some benefits can even be reviewed, but be cautious about touching anything relating to people’s sense of security such as health insurance, life insurance, retirement accounts, etc. 40

Chapter 3

Culture

E xplore Staff Cost Reductions That Don’t Eliminate Jobs Cost reduction and elimination are two different things, but when we’re sitting in a room trying to find ways to reduce staff costs, we default to eliminating jobs and going through redundancies. In one startup I’ve been part of, the CEO initiated a series of staff cost reductions that made a significant impact on the burn rate and didn’t require anyone to lose their job. Here’s what they did: •

All members of the leadership team took a pay decrease.

•

No bonuses were paid or budgeted for.

•

All pay increases that year were frozen, except for those below an income threshold.

•

Employees were offered the chance to go part-time temporarily. Some took that option.

•

Some employees were offered to transition and be trained up in new roles when their team workload reduced. All of them took up that offer.

Do It Right and Look After Your People If every other option has been exhausted and the business must reduce the size of the team, I urge you… do it right. Your business is worth nothing without your people, so look after them. There could be an entire chapter on this so I’ll summarize the most pertinent points.

41

Chapter 3

Culture

Communication Your communication plan should be thoughtful, comprehensive, and sensitive. This means, at a minimum, that every single person in your company or the affected teams have several touchpoints of communication, both verbally and in writing. This should include a one-to-­one conversation for both those whose roles are impacted and those who will remain. If you do not have the expertise in house to do this, go and get it. Please, do not attempt a workforce reduction if you’re never done it before. I’m all for learning on the job, but in this case, learn from someone who has done it before and done it well. If you have investors, reach out to them first as they’ll likely have connections and can refer you to someone who can help.

Severance Never forget that the people who are impacted by this decision are exactly that. People. Who might have kids, a mortgage, travel plans, caring responsibilities, health concerns, and all sorts of other things. The statutory redundancy payment in most countries is the minimum payable, not what you should be aiming for unless a meaningful severance is going to compound the financial problems. This may sound a bit counterintuitive, but if you’re laying off 10% of your workforce, you can definitely afford meaningful severance payments.

Benefits In a similar vein to severance, the benefits offering and continuation of these is a must-have. This is not the time to strip away employment from your people, and then leave them high and dry without many benefits and coverage that can be tricky to replace while looking for their next gig. Make sure healthcare coverage is continued as much as you’re able to in their country of employment. Ensure outplacement and mental health support is on hand for at least three months after someone leaves. And if you offer 42

Chapter 3

Culture

equity, don’t put your people in a position where they have to fork out huge amounts of money to exercise their options in a company they’re no longer part of.

Diversity A forgotten step most of the time. We’ve already discussed bias and how it can impact recruitment decisions. The same thing applies here and the same level of calibration is required. Be mindful of your legal obligations too in this space, especially around those on extended leave or who have a protected characteristic.

Redeployment If you’re trying to reduce the team size in one area of the business and continue to grow in another, redeployment needs to be front of mind. While you may feel some or many skills are missing from those who are impacted in one part of the business, don’t forget the knowledge and skills that they do have. The inside know-how, relationships, understanding of your customers and product, and the fact they are already in your business. The cost of training and redeploying will almost always far outweigh the cost of hiring externally.

Find a Common Language When you double (or more) in size, communication becomes just that little bit harder. It takes a bit longer for messages to sink in. It might take several attempts to communicate. You might have to adjust mediums or invest in new mediums to find ways to best connect with a growing team. That’s where a common language is helpful to bridge communication gaps and the conflict that naturally emerges. I’ve found three forms of common language help to add some glue to the culture and support growth of the team. 43

Chapter 3

Culture

Values I’ll come on to values more deeply in the next lesson. Once they’re documented, build them into recruitment steps and performance feedback processes. Talk about them regularly. Recognize others for how they live and role model the values. Deal directly with behaviors that aren’t aligned to the values. They are the strongest glue that exists in a culture and have the power to drive common behaviors across teams and ensure you attract people who are going to excel in your company.

Ambitions and Goals I have a bit of a checkered background with Objectives and Key Results (OKRs) as a company-wide goal methodology. One day I’ll nail it, but having been underwhelmed with how I delivered these in the past, it’s taught me something even more important. The value and importance in every single team member knowing exactly what the company is trying to achieve. This shared understanding helps to keep people pointed in the same direction and fosters good conversation around how we invest our time and resources. Without transparency and symmetry in this information, you create forks in the work people do and end up needing to spend time realigning on priorities. If you’re a CEO reading this, the test for goals in your company, regardless of how you choose to structure these, is that every quarter you should ask a random handful of people across teams and levels to articulate the goals back to you. Make sure they don’t think it’s a test and they know you want to check how well they’re communicated. The aim is that every single person you ask can describe them, whether they’re your VP Sales or a Graduate Software Developer, and understand why they are important.

44

Chapter 3

Culture

Work Styles As teams inevitably grow, tension and conflict becomes normal. It’s nothing to be afraid of. Great teams have conflict and work through it constructively. But one of the most difficult things when conflict exists is being able to understand where other people are coming from and being able to safely describe what is taking place. Typically, we apply judgment language to what we observe. Tim is not being direct, he’s being rude. Alice is not being thoughtful and considered, she’s being slow. Ryan is not being sociable and energetic, he’s annoying me because he doesn’t shut up and let me speak. I’m a big fan of the Insights Discovery tool and framework to help build a common language around what we observe in others and ourselves in the workplace. How we communicate, behave, manage, make decisions, and perceive things. All difficult to describe because we struggle to know what words to use. Instead of being frustrated that someone wasn’t on board for a project we were experimenting with, we could instead become curious as to whether they had a need for more concrete details and data behind the decision, and start a conversation around that. There are lots of tools out there that might help with this, but for me I keep coming back to the simplicity of Insights to help navigate the complexity of human behavior.

Getting Past the Values Fluff You walk into an office to interview for a new job. You’ve spoken to a recruiter and things sound good so far, but you’re still working out if this is the right company and role for you. Culture is important and you’re wanting to look under the hood and check that this is what you’re looking for in your next gig. You approach reception to let them know you arrived. Plastered behind the receptionist you get a glimpse of the company

45

Chapter 3

Culture

values and hope that they give you a bit of insight into the culture: respect, integrity, and professionalism. How helpful. At this point in my career, I have pretty polarizing views of company values. I have seen just how powerful they can be when they articulate specific, unique, and embedded parts of a company culture and just how sticky they can be for teams to encourage mindsets and behaviors. But too often I’m left reading the company values on a website and not knowing much about the company at all afterward. Take something like integrity. Integrity is a minimum requirement and expectation for running a company. While I’m sure some folks adopt practices that lack integrity, it’s a license-to-operate trait of your company, not a value. Great company values help define who you are as a company and what makes you “you”. Every company should have integrity. And respect. And professionalism. So what do you have as part of your culture that makes you “you”? The best way a company value has ever been described to me is through the lens of a trade-off. The trade-offs you make highlight the values you have. You might value transparency, but are you willing to be transparent even when things are uncomfortable, or if the message is a bad one? That’s the trade-off you make when you value transparency. It’s not required of you, but you’ve chosen to behave in a certain way that indicates what you value. I’ve also found questions like “what does a high performer look like here?” and “how do we make decisions?” to be helpful questions to help elicit insights on the values of a startup. Once values are identified, the trade-offs for each will help to inform the next level of detail which is to articulate the specific behaviors that demonstrate that value. This is hugely important as how one person views transparency will differ to the next. The trade-offs help everyone in the company understand how to apply that value to how things get done in the business. This is also the level of detail that will help inform how you hire, manage performance, and recognize people.

46

Chapter 3

Culture

This chapter has covered a handful of traits and implications of the work we do around culture, but you may have noticed it was absent from a lot of what we’re learning about how the work we’re doing to build diversity, equity, inclusion, and belonging can impact on the culture and experience of our people. The next chapter is called Inclusion, a chapter close to my heart and critical to how we build startups.

Summary –– Culture is a fluid fabric of systems and behaviors. It’s how stuff happens, not what’s in the fridge. –– Culture fit and culture contribution are currently fighting for attention, but it’s never been an either/or battle. When you’re building your team in a startup, you need to be looking for both. –– Put a common language around the business and culture as you grow. It helps you work through conflict, focus on culture fit and contribution, and build alignment to goals. –– You can’t be values-led without a significant trade-off to demonstrate it. Narrow in on the trade-offs you make that demonstrate what your values might be. –– While process is important at times, overusing it in growth-stage companies starts to chip away at the pace and agility that likely differentiate you from bigger players in the market. Things will slow down and become more structured at some point, so best not to force it prematurely.

47

Chapter 3

Culture

–– Reducing the size of your team is a last resort, not a first one. Exhaust every other option first to reduce spend, look for ways to reduce staff costs without losing jobs, and if you need to make that difficult decision to let people go, your people deserve for it to be done sensitively and generously.

48

CHAPTER 4

Inclusion Inclusion hits home for me, so it only felt appropriate to have a chapter dedicated to it and some of the lessons I’ve learned both within and outside of startups. With this chapter, we’ll have covered the impact, shaping, and shared understanding of leadership, culture, and inclusion, before we then tackle some of the specific areas in the People lifecycle that influence the experience we’re crafting. I covered my sexuality for years before I felt safe enough to share that part of my identity with those around me. That’s not just a work story. I covered it from everyone, a common experience for the LGBTQ+ community. But I saw the work side of it too. The unease I felt when a supervisor was scared that a gay man would hit on other men in his team or the guilt I felt lying to my teammates when they would ask if I had a woman in my life yet. This has nothing to do with my managers either. I couldn’t have asked for better managers throughout most of my career. I’ve been very fortunate on that front. This relates to embedded, cultural norms for what was accepted, believed, and tolerated in a number of businesses I was part of. There was no way this book would ever be finished without dedicating a chapter to inclusion, and there are a few reasons for that. The first reason is my own experience. This book started as a journal of things I was learning and things I didn’t want to forget, and my own experience and perspective on inclusion features frequently. Another reason is the constant reminder of just how far we have to go before every single workplace is somewhere people feel belonging, safety, and acceptance. © Patrick Caldwell 2023 P. Caldwell, People Ops, https://doi.org/10.1007/978-1-4842-9819-0_4

49

Chapter 4

Inclusion

And the last reason is how integral the work we do in this space is to every other part of people and culture in a business. You can’t convince me you’re serious about culture and leadership which we just covered in the last two chapters, or performance and reward which we’ll cover later, without showing me first how serious you are about inclusion. As a small disclaimer, I’ve called this chapter inclusion and I use that word quite frequently throughout. It’s how I’ve come to understand parts of my own experience. I know the work we’re doing is much broader than that, and captures accessibility, belonging, diversity, equity, and justice. For consistency, I’ll use the acronym DEIB for diversity, equity, inclusion, and belonging as that most accurately describes the experiences and perspectives I share in this chapter.

Inclusion > Diversity Earlier in my career I was given some “advice” by a colleague that I should be mindful of my body language, otherwise people would think I bat for the other team. And one of the first times I told someone in that workplace that I was gay, the response was asking me whether I wanted to be on the company’s LGBTQ+ parade float that year. Not bad for a company who touted their LGBTQ+ awards and credentials. I don’t know about you, but there are very few things I find more misguided than reading a company’s DEIB plan and not seeing anything more substantial than representation targets and broadly stated intentions around equity, inclusion, and belonging. One of my favorites is just how many companies of all sizes believe that by sprinkling some visible diversity into its senior ranks that they’ve solved the rest of the acronym too. A HR leader even tried to convince me that more women on teams would lead to greater inclusion across the company, so the focus needed to be on “only hiring women.” I have no doubt some good intentions are buried in there somewhere, but unfortunately we’ve hit rock bottom 50

Chapter 4

Inclusion

where the average company has stripped back DEIB to nothing more than making sure there is some visible demographic diversity and a few rainbows and cupcakes throughout the year. The obsession with showing people something visible, and perhaps the fear of being seen as not doing anything visible, should never have replaced the need to actually do the work to become a company where everyone, in whatever way you choose to define diversity, can be successful and contribute to the company’s success. A team representing 20 different demographics can be full of conflict, disharmony, and exclusionary behaviors. Similarly, a completely homogeneous team across the same demographics can demonstrate a high level of inclusion and belonging. Let’s apply this to a small and fast-growing company. The value of diversity comes from diversity of thought. It’s critical to a small company looking to innovate or disrupt a market. In my experience, what we call diversity now in terms of demographic diversity is simply a proxy for embedding more diversity of thought and reducing the inequities that have prevented this from being accessible in the past. But aiming for diversity without inclusion, equity, and belonging is just setting the company up for great talent to leave. Each time I’ve come into a startup, I’ve learned to start with inclusion. And there are two pockets in startups that are full of actionable insight and opportunities to build inclusion.

Leadership Calling out behaviors and actions that don’t promote inclusion. Observe team meetings, communication, how decisions are made, and who is involved. There’s no sugarcoating this and I’m starting with it for good reason. It’s hard work and all sorts of uncomfortable, but if you’re a senior people leader or, better yet, a founder, you’re in the best seat to do this. I’ve found a happy ground somewhere between “not trying to make friends” 51

Chapter 4

Inclusion

and “not approaching things with a stick,” which is to use observation feedback models to identify specific behaviors that don’t drive inclusion and suggest an alternative way for a better result. Most people are willing to do this, even if it takes a few goes (yes, change can take some time). If they aren’t willing to try, they shouldn’t be part of your company.

Backyard This is a catch-all for the people systems, policies, and processes which are part of how your company runs. It’s how promotion decisions are made, how recruitment takes place, career development opportunities, pay gaps, and benefits. All of these areas are carriers for exclusion and reinforcing stereotypes which makes a great stomping ground to make genuine impact. Take something like parental leave where, in most countries, it’s designed to support the notion of a childbearing woman taking an extended period of leave to care for a child while a man takes a long weekend and returns to work. Now consider how your parental leave applies to different circumstances and family structures. Adoption. Surrogacy. Same-sex couples. Single parents. Stillborn and miscarriages. Heck, even dads in the stereotype above who were prevented from more time with their new bundle of joy. When you consider the breadth of circumstances relating to parents, most company (and statutory) parental leave structures are highly exclusionary and reinforcing of stereotypes. Not convinced? Reach out to a half dozen parents in your network who don’t fit the stereotype described earlier and ask them to share their experience of parenthood and parental leave. That was how I came to the realization that I needed to rethink everything about parental leave in the companies I work in.

52

Chapter 4

Inclusion

Pitch at 80% This isn’t exclusively for this chapter and it builds upon the “Done > Perfect” learning in Chapter 1, but it originated in my work in this space and I’ve come to accept it as a personal principle in pretty much every part of my work. In fact, it even applies to the publishing proposal my publisher received for this book and, thankfully, that seemed to go OK! While my career in more recent years has been in the startup scene, I used to work in a really large company and corporate environment. Between the number of stakeholders needed to get something over the line and the number of people impacted by the decisions, I found myself making sure something was as perfect as I could make it before I brought anyone into the fold. This isn’t bad behavior, just symptomatic of how I was operating at the time and the environment I was in. On advice of a mentor, I started to push myself to share ideas and push for changes when they were roughly 80% done, either in terms of planning for projects or even 80% baked in my mind for sharing my thinking. The thinking here was twofold: nothing is perfect anyway, so pace of delivery and having impact sooner rather than later outweigh the other 20% of perfecting; and it was important for me to get used to the fact that things fail often in startups and that’s OK, so assuming what I’m proposing is reversible if things don’t work out, I should accept the higher risk of failure and get comfortable with that. Pitch at 80% is the result of this and something that feels more comfortable now than what it used to. When a thought is 80% baked, I’ll share it for others to provide their perspective on. It ensures I never get so hell-bent on having the right solution that I’m not open to others’ ideas and feedback. And when my work is 80% complete and the remaining 20% is just perfecting it, I’ll get it out into the open or, better yet, make it live and trust iteration to fix the rest.

53

Chapter 4

Inclusion

 e Judged by Your Actions, Not B Your Intentions I presented this learning and now principle on a video call with 30 or 40 team members of a company as part of a DEIB presentation. I was asked to speak and share the initiatives and progress we’d made in the startup I was part of. I can’t remember the exact phrasing of how I introduced this, but it was along the lines of “don’t believe anything until it happens.” I probably looked like a bit of a pessimist but I’m not sure that’s ever a bad thing in the DEIB space these days. Optimistic with a healthy dose of caution and skepticism might be a better way to put it. The DEIB space is flooded with good intentions. The company sprawled over social media for injustice telling everyone how much they care about the feedback and experience of employees and how committed they are to change. The company with a 20% gender pay gap reflecting on International Women’s Day about the incredible women who have been integral to their success. And let’s not forget the company pocketing profit after adding a rainbow to their product range for Pride. These are all actions from companies we’ve sadly become accustomed to. In one of the first startups I worked in, we made a deliberate choice to reframe our communication in the DEIB space to being about what we had done, not what we were planning to do. While we knew the areas that required change, the act of sharing plans can sometimes trap us into thinking the work has been done. And when we’re called out on that, we repeat the vicious cycle of making clear our intentions and plans. Intentions are cheap. For progress to be real and impactful, we needed to be accountable for our actions and the results of our actions, not for what we were planning to do. And so that is what we told our people. Judge us by our actions, not by our intentions.

54

Chapter 4

Inclusion

In the years ahead, DEIB in this startup felt different to any other company I’ve been part of. We used data to inform our progress and areas that still needed work. The gender pay gap reduced from some absurd number to near 0%. Policies and people processes were continuously iterated and then tested for feedback in terms of the impact they had. Churn did not disproportionately impact some communities over others. Neither did engagement scores. When we were asked to share our DEIB Strategy or Policy as part of an RFP process or through due diligence, we took pride in saying “We don’t have one, but here’s the impact we’ve had.” And if you needed any more convincing about why Inclusion > Diversity from the start of this chapter, the diversity of our team started to increase on a whole host of different demographics. Not because we set targets and had DEIB plans in place, but because what we had achieved and built was now resonating with a much larger population.

Get Under the Skin of Your Gender Pay Gap It’s hard for this to not be the next logical learning given the focus so far on inclusion and accountability. Time and time again, I find the gender pay gap to be as divisive as it is telling about where a company is at in their DEIB journey. And regardless of the arguments for why and how the gender pay gap emerges in a company, doing nothing or even settling for incremental progress can’t be the solution. “It tells me if I’m valued and how much I can earn here.” These words from a woman I worked with sum up everything that People teams, leaders, and founders need to know about the gender pay gap. It’s also just as relevant to any pay gaps that exist across other demographics and can highlight where inequities exist through other decision-making or people processes which need some love, such as recruitment and promotions.

55

Chapter 4

Inclusion

For the purpose of this mental note though, I’m going to refer only to the gender pay gap with what I’ve learned in startups being applicable almost identically across other demographics too. One of the biggest misconceptions around the gender pay gap is that you fix it by paying the lower-paid gender more. Sure, you could grab some duct tape and make it look better, but this ignores the actual problem. Work in this space needs to look not only at what has happened historically and what the data says, but also what caused it to exist that way in the first place and what changes to company processes can prevent inequity from creating the same problem in the future. There is nothing about the gender pay gap that is accidental. We created it. Depending on where a startup is incorporated and operating will depend on when legislation makes reporting on gender pay gaps mandatory. But the best time to start, whatever stage you’re at, is right now with the data you have available. In a nutshell, there are two types of pay gaps and both are important to analyze as they’ll tell you different things: equal pay gap and gender pay gap. The equal pay gap, in its simplest form, means the same pay for the same work. There are valid reasons why pay might differ within roles such as through a performance process, but the heart of equal pay is really testing the structural and systemic issues that result in a gender pay gap. In many countries, where there are no valid reasons why pay differs, it is considered a breach of law. The gender pay gap is the more nuanced of the two. Compare the average hourly earnings of men to the average hourly earnings of women. The percentage difference between the two is your gender pay gap. Let’s say you have a gender pay gap of 10%, meaning that the average hourly earnings of women are 10% less than that of men. There are lots of reasons this might be the case, but regardless of the reasons, the gender pay gap still exists. The average woman, regardless of role, tenure, and seniority, can expect to earn 10% less than men in your company.

56

Chapter 4

Inclusion

If you have a big enough data set, you can cut this across roles, tenure, and seniority to see if you can pinpoint some insight around what might be causing this. In startups I’ve been part of, we’ve identified a bunch of reasons why a gender pay gap exists: •

A leadership team made up of mostly men

•

A higher proportion of women in part-time roles which had lower average hourly pay than full-time roles (lots to unpack in that one, but more common than we might hope!)

•

Technical teams made up of mostly men where salaries were higher than nontechnical teams

•

A higher proportion of women in entry-level or junior roles, often as a result of trying to increase gender representation and immediately going to the graduate and entry-level roles where recruitment pipelines are more balanced

Each one of these tells a story of something that is relevant to the outcome. They may not be directly related to pay, but they influence the outcome. And back to the misconception around paying the lower-paid gender more, we could indeed do that, but none of the preceding examples are actually changed by that. We’re just re-creating the problem to exist again but with a different baseline. In the previous learning around actions and intentions, I mentioned a startup where we brought the gender pay gap down to almost zero. There were three areas we focused on which over a three-year period demonstrated year-on-year reduction to zero. And just in case you were thinking this, no, it didn’t then create a gender pay gap the other way. It stayed within a couple of percent either way of zero consistently after that. These changes were not designed to increase one gender’s pay, but rather to remove the reasons why one gender’s pay was increasing disproportionately to the other. 57

Chapter 4

Inclusion

Area 1: Recruitment Recruitment is a deep pit of behaviors, systems, and processes that contribute to pay gaps. We started first with reviewing all of our language and job requirements to broaden the pool of candidates who would read our post and be excited by what they could contribute. Narrow salary ranges were added to all advertisements to remove asymmetry of information. We then built a standardized approach to hiring stages and calibration of decisions to avoid any unwanted effects of bias. I’ll come back to this in the next lesson. Our final piece in recruitment was the “best offer first” principle which leveled the negotiation playing field that, historically, disproportionately benefits men.

Area 2: Progression Up until 50-ish people in a startup, progression isn’t much of a thing especially if you’ve grown quickly to get there. The early dozen or two team members don’t usually have progression as one of their top draw cards and, frankly, organizational structures that early are fluid and messy. That’s not an excuse to not care about it. It’s just something that tends to be down the priority list when you’re desperately trying to build and ship a product. Plus, it’s not normally something that will break the organization immediately if you don’t have much in place. Key word there is definitely immediately. In my experience, during periods of intense growth in the early stages, progression decisions are typically made on the trust of the founder(s) or CEO. Add that to unclear leveling and role scopes, lack of internal recruitment processes, and a healthy dose of urgency culture, and it’s not hard to see how progression decisions can perpetuate imbalances in both representation and compensation. We focused on leveling and role definition (i.e., levels of authority, responsibility, influence, and contribution), and paired that with a formal internal recruitment processes 58

Chapter 4

Inclusion

with diverse panels and calibration of decisions. In under two years, the percentage of women promoted increased from roughly 25% to just under 50%, and the percentage of other underrepresented populations also increased but to a lesser extent. We focused on the process that caused the imbalance and allowed it time to demonstrate impact.

Area 3: Compensation Framework OK, I’ll admit that frameworks around compensation can be a bit divisive. I’ve dedicated an entire chapter to it, but in practice, there have been enough lessons throughout my career on compensation to fill a separate book. But for the purpose of this lesson, I want to target one specific element of a compensation framework which is the benchmarking and structure of compensation ranges and levels which form the spine of any good framework. This was single-handedly the most impactful initiative we did to reduce the equal pay gap. We defined and leveled every single role in the organization, sourced multiple, reputable data benchmarking sources, and built a philosophy behind how we set salaries using ranges that were informed by that data. The reason why this is so impactful is twofold. Firstly, it takes most of the guesswork out of it. Sure, you’re not going to impress everyone with this (remember “Ground Your Decision-Making”), but adding a dose of data corrects the imperfections of how humans approach compensation. And the ultimate test should always be if you can easily justify your decisions to an open room of everyone impacted by it. The second reason this creates impact is because it allows a swift rectification of errors and the history of imperfections that have been built up. The first time I built a compensation framework and applied the principles, it reduced the equal pay gap to 0% and the gender pay gap significantly too (not to zero though as that didn’t happen for a couple of years). Fixing the structure meant we could focus on other barriers without the anchor that would be a systemic issue like the compensation framework. 59

Chapter 4

Inclusion

The Myth of Removing Bias I am biased. You are as well. But there’s no need for either of us to be defensive about it as, unlike we are led to believe, bias is unavoidable. As humans we are a collection of experiences, perspectives, norms, beliefs, and products of our environment. These shape everything we do and how we see things. So it should be no surprise that bias comes up so frequently in DEIB conversations. Yet for the last ten years the majority of training sessions and presentations I’ve attended around bias have focused primarily on how you can root out bias and stop it. You can’t. With some deep introspection and a lot of self-awareness, you can be hyperaware of your bias. And over time it’s likely possible that bias can change, as does the lens through which we view the world. But you can’t stop it completely. I remember the first time I did one of those implicit association tests as part of a training session. It showed that I displayed a handful of positive and negative biases toward a whole bunch of different demographics. No doubt incredibly useful to reflect on and I think about it often. But in this training session, we weren’t reflecting on bias or what to do with that information. We were holding up results arguing who was better. Celebrating results that were less strongly weighted than others. And treating bias like something we should be ashamed of and hide from. It was a friend’s perspective during a rant we were having about bias which felt so perfectly articulated and captured the frustration in my mind. It immediately featured in my mental notes. “Don’t be scared of bias. Be scared of letting bias play out in your company”. The fact I have biases built up over my lifetime and influenced by the experiences I’ve had is not something to be ashamed of. It is something to identify. To understand. And to make sure that those biases don’t influence the decisions and choices I make. And as a People Ops leader, it’s my job

60

Chapter 4

Inclusion

to have processes and systems in place that can do this at scale across how the company operates. To calibrate decisions and broaden the input. To enrich conversations with different perspectives. To call out behaviors or gut feelings that people don’t want to elaborate on. And to help others become curious about their own biases and build the awareness to identify how they might play out. This chapter felt personal to write and share, because it is. It’s personal to everyone regardless of their background and something we simply can’t afford to not get right if we’re serious about what we’re building. In the next chapter, we start our exploration of specific parts of the People lifecycle and experience, kicking off with Recruitment.

Summary 1. Representation matters, but it can’t be the sole aim of your DEIB work. Start with inclusion and focus on the pockets of the business at high risk for non-inclusive outcomes (e.g., leadership behaviors, communication and meetings, policies, and processes that impact people directly, such as recruitment, leave, and promotions). Getting this right adds credibility to the other work you will need to do. 2. When something is 80% formed in your mind, start sharing it with others for input and feedback. The remaining 20% will allow for buy-in and prevent perfectionist behaviors from delaying something that can deliver value.

61

Chapter 4

Inclusion

3. The DEIB space is flooded with good intentions, but our actions and results leave a lot to be desired. Intentions are worth nothing. We are accountable for what we deliver and the impact it has, which is the standard we should apply to any DEIB work that we see. 4. The gender pay gap has become a divisive topic but is ultimately a test of so much more in the people space than just compensation. Getting under the skin of what drives it, where inequities exist, and how to right these allows us to tackle the problem at the core, not just try and manage the symptoms. 5. Bias is a normal, unavoidable, and human experience. We shouldn’t be scared of it or try to deny its existence. We should be scared of letting it play out unchecked.

62

CHAPTER 5

Recruitment Now that we’ve looked under the hood at leadership, culture, and inclusion that sit throughout every part of the People space, it’s time we tackle the very start of how our people experience startups: recruitment. This chapter is bittersweet. The state of recruitment has a long way to come, but hopefully after this chapter, you’ll be excited as I am by what is possible if we reframe recruitment in a more people-centric way. In 2022, I decided to run a bit of an experiment and set up an AskHR-­Anything thread on a careers forum. The forum is anonymous so I wondered if it might prompt some radically transparent perspectives on HR. Plus, if it meant I could help a few people out who might be in pickles, then it was probably worth it. About 50,000 views and almost 2,000 responses later, there was enough insight and material to write an entirely separate book. Once I got through the deeply offensive and abusive comments that the keyboard warriors posted, the single most concerning area was hearing about the state of recruitment. From people who were laid off, had applied for hundreds of jobs, and rarely ever heard back. To those who went through ten stages of interviews only to be ghosted and not receive any feedback. To hard-core task rounds where candidates would work for days on end, basically as free labor, to produce presentations and initiatives that would help that company and then be told the role was on hold. There was even someone who traveled hours by car to get into a city, bought new clothes for an interview, turned up at the office, and was told the interviewer was not in today and they needed to reschedule. © Patrick Caldwell 2023 P. Caldwell, People Ops, https://doi.org/10.1007/978-1-4842-9819-0_5

63

Chapter 5

Recruitment

I’m not blind to how much repair work there is to do in HR and how mixed the experience is. But this thread was so hard to read. It doesn’t matter the industry, country, or profession, candidates everywhere are being treated like shit in our hiring processes, and it’s become so consistent that we’ve learned to accept it as normal. One day I might dedicate an entire book to this topic, but for now, here are some of my learnings and musings on recruitment from scaling startups.

 espond to Every Single Job Applicant R As Though Your Brand Depends on It You're scrolling through LinkedIn seeing if your next opportunity might be out there. You stumble across a really interesting role. The company looks great. You meet the requirements they've listed and you start to get excited. You open up your CV and start to mold it for this role, calling out things in your background that are most relevant. You put together a cover letter making it crystal clear why you're excited by the role and what you can bring to the company. You attach the documents to the application, answer some questions about yourself, and click send. Done! And now the waiting game starts. You check your emails in the days afterward hoping for a quick and positive response. Then a few weeks later you still haven't heard back and you start to lose hope. You never hear back. I once shared this scenario at a conference talk in front of a room of recruiters and asked everyone to put their hands up if they've experienced a company never getting back to them after applying for a job. Almost the 64

Chapter 5

Recruitment

entire room put their hand up. I then asked those people who respond to every single job application they receive to put their hand down. A small handful put their hands down. Around three quarters of the room kept it up. The job application process is broken. We've created a norm in companies where candidates are inferior. We then prove it to candidates with disclaimers on the bottom of job advertisements like:

Due to the high volume of applications we receive, we are unable to respond to every application and will only be in touch with those who will progress to the next stage of the recruitment process. As a candidate, this is read as:

Despite me investing 30 minutes of my time putting together a thoughtful application, you can't find 30 seconds of your time sending me an email to say I've been unsuccessful. The irony of this scenario lies in the fact that those companies who receive such a high volume of applications will almost always have an applicant tracking system (ATS) in place that allows for bulk rejection emails, and those who don't have one in place are unlikely to be receiving a high enough volume of applications to justify why they can't respond with a friendly “no” to provide the applicant some certainty. In both cases the reasoning usually lies somewhere between laziness and disrespect for the job application process. As a job candidate the only thing worse than a rejection email is hearing nothing back at all. It's both the sense of rejection and hope combined. As a People profession, we have to change this norm. Instead of telling applicants on the advertisement that they may not receive a response, tell them how long they can expect to wait before receiving a response. And hold your teams and hiring managers accountable for ensuring every single applicant receives a response if they were successful or not.

65

Chapter 5

Recruitment

Start with Your Best Offer and Don’t Budge If it wasn’t bad enough for candidates to navigate a broken job application process, unfortunately the offer and negotiation process isn’t much better. Companies are generally focused on keeping the offer within budget which unfortunately is interpreted by HR and hiring managers as keeping the offer as low as possible. Candidates are, rightly so, focused on getting the best offer they can. And neither side to this equation is particularly motivated to speak transparently first about their expectations. Job searching and recruitment processes are really unforgiving. At the point you’re speaking to a candidate, it’s likely they’ve faced delays, radio silence, and rejection. It also represents something far greater to the candidate than it does the company. For that reason, I’m always of the belief the responsibility to mend this should start with the company and it’s the reason I now, almost religiously, use a set of principles to guide the offer experience: •

66

Transparent salaries: Share the salary range on the job post. There are some roles, despite opinion, where this is actually really tricky in a startup. These are usually roles that carry significant equity or variable packages where the makeup of the package is flexible in order to land the right hire. But for the other 98% of roles, there is zero downside to posting the range on the role in order to manage expectations from the start. If you’re worried about what existing team members will think when they see a salary range that might be higher than what they are on, you need to fix your own backyard first.

Chapter 5

•

Recruitment

Screening: In the initial screening conversation, discuss the salary range again and aim to understand the expectations of the candidate. If you’re up front about the salary range on offer, most candidates will share their expectations with you. Two things to be mindful of here: 1. If you share a range with a candidate, it is human nature for the candidate to share their expectation at the top of that range. Don’t be annoyed, you would do the same in their shoes. I find it’s helpful to also articulate how the salary will be set within that range in order to ensure parity with existing team members and reflect how their capability and skills are assessed in the recruitment process. 2. Some candidates will tell you their expectation is above the range with the hope the range is flexible. Again, don’t be annoyed. There are a lot of reasons why a mismatch of expectations exists. When this happens, I’ll usually reconfirm the range with the candidate and what the upper limit actually is, and ask them, “if you were successful in this process and we offered you [insert upper limit salary], would it be a dealbreaker for you?.” If the answer is no, you’ve set a reasonable expectation for the candidate as to what is coming to avoid surprises. If the answer is yes, you’ve saved time for both you and the candidate for a role that is just not a fit.

67

Chapter 5

•

Recruitment

Best offer first: At the offer stage, I use a “best offer first” principle and I’m explicit about this with candidates. This isn’t some fluffy way of polishing a low ball. If you’re going to use this, it must be genuine; otherwise, there’s zero value in it. Best offer first refers to discussing internally at what point someone could keep negotiating before we eventually say no. Let’s say you’ve set a range of 60–70k. You offer 64k. If they really pushed for more, you realize you would be open to 66k, but any higher would sacrifice parity within the team. You should just offer 66k and don’t negotiate. There are a few things I’ve come to observe and realize from using this approach: 1. You must be explicit about what you’re doing. Share the principle with the candidate. Tell them how you arrived at that number and that it’s the best offer first with no room to negotiate up. And remind them the criteria in your decision is based on where you’ve positioned them within the range and why, and the high-level summary of how that compares with existing team members. If you are not explicit about what you’re doing, they are at risk of just assuming they are being lowballed. Because let’s be honest, this is exactly what happens in most offer situations. 2. I’ve used this principle in three different startups now. In every startup, the offer acceptance rate increases and the time to respond at the offer stage decreases. If you’re genuinely doing good by candidates, they’ll recognize it. And the company benefits from higher and faster conversion rates.

68

Chapter 5

Recruitment

3. Be mindful of cultural differences. I first introduced this in a European setting and the results were immediate. When I introduced it into a US setting, it was more problematic. Candidates would come back a few days later trying to negotiate it up, often above what was shared as the salary range. We discussed this within our US team and one of our sales team members reminded me how ingrained it is for her to never accept the first offer regardless of how good you might think it is, and if you don’t ask you don’t get. I respect that. It just makes the best offer first principle a bit slower. In the US setting the time to respond decreased but immaterially. The offer acceptance rate still increased in line with other regions, but we’d often find ourselves in a negotiation conversation simply saying no and reminding candidates of the best offer first principle.

 our Candidate Experience Is As Important Y As Your Customer Experience If you’re in a company where your candidate is also likely to be a customer, this learning will probably resonate more clearly. After all, you don’t want to piss off a candidate who might already be or is considering becoming a customer of yours. In a “to-business” setting, this link can be easy to forget but I’d argue it’s still just as important. In startups, we think about the customer experience often. Daily. But rarely do we hear conversation of the candidate experience unless you have a well-developed talent acquisition team. In the same way we map out 69

Chapter 5

Recruitment

the customer experience, it can be helpful to do that for the recruitment process too. Identify the purpose and aim for each step of the recruitment process, starting with how a candidate will initially discover the company and experience a showcase of culture in an authentic way. Then, speak to all new hires in the last six months to understand their experience of the recruitment process, in particular what they found was helpful and valuable and where things weren’t as sharp as they could be. Be mindful that your new hires were successful in your recruitment process so they likely only represent a very small percentage of the candidate experience. Consider building feedback mechanisms into various stages of the recruitment process. If you’re setting up templates in your ATS to progress someone from screening stage to interview stage, you can build in pulse check scoring and a focus question to get some real-time input. A focus question like “What is one thing we could have done to make your first stage interview even better?.” Another key part to candidate experience is speed. Gone are the days where it is acceptable for someone to receive an invitation to a screening stage six weeks after they applied. Similarly, waiting weeks after an interview is a surefire way for the candidate to lose excitement in the role. I use three targets and metrics in the recruitment process to provide insight into speed: 1. Time to respond to an application: two weeks 2. Time to hear back after a main stage interview: three days 3. Time to hear back after a final stage interview: one day There are, of course, instances where other interviews need to be conducted before arriving at a decision. When this occurs, we use the same targets but from the end of the last interview. If you don’t have an automated way to collect this data yet, you can still embed a positive candidate experience around speed into your process. At the end of each stage of a recruitment 70

Chapter 5

Recruitment

process, let the candidate know when they’ll hear back from you. It creates some accountability between you and the candidate, and it helps manage expectations so the candidate knows when it’s the right time to follow up.

Turn the Tables To make the best use of this time, I’d like to spend the first half of this interview with us getting to know more about you and what you can bring to this company. Following this, we’ll turn the tables so you can interview us and make sure you have enough information to know if this opportunity is right for you. And for the final few minutes, I’ll cover the next steps in the recruitment process and when you can expect to hear back. It’s easy to forget that a recruitment process is a two-way assessment. Companies are trying to work out if someone is the right hire for the role, and candidates are trying to work out if you are the right company for them. It begs the question as to why so much of the recruitment process is a one-way assessment. In the past when I’ve been hiring into my team, I’ve often used the turn the tables approach as part of a main stage interview to provide space for candidates to get under the skin of the company and understand if it’s the right fit for them. The more a candidate can learn about the role, team, company, challenges, culture, and manager, the more armed they are to self-select in or out of the recruitment process. Both self-selections are valuable outcomes to a recruitment process.

Don’t Join This Company If… One of the questions I was asked by a candidate during a turn the tables interview has stuck with me for years. Amusingly, it’s also a question I make sure to ask any company I am speaking to about a potential role also. 71

Chapter 5

Recruitment

Who shouldn’t join this company? I like this question for a number of reasons. Firstly, you’re reframing a question in a much more pointed way that allows you to get under the skin of the culture of the company. Secondly, it’s really obvious to the candidate when someone is full of it when they answer. You can’t waffle your way through it. You’re forced to think about the circumstances in which someone might not be the right fit at the company. And that’s a really helpful thing to know up front, for both the candidate and the company. As a candidate, I find the answers I’ve received from companies have carried more emotion and authenticity in the response. I’ve learned about previous people who they’d parted ways with. I’ve learned about cultural challenges they have and are working through. I’ve discovered fears and concerns of the hiring manager and also what is going to be important for them. It’s also become a go-to question when briefing new roles with hiring managers. It helps understand specific behaviors or mindsets that can be tested early in the hiring process, and in a similar way to interview situations, it’s often an unexpected question that forces an authentic and emotional response.

T he Candidate Was Great! I’d Like to Meet a Few More Though A pet hate of every talent acquisition professional. You’ve expedited an incredibly talented candidate to an interview with the manager. They might have come through an application process or someone you’ve been proactively nurturing until an opportunity arises. The manager interviews the candidate and it goes really well. And then the dreaded comment… “I’d like to meet a few more candidates in order to compare.” Face palm.

72

Chapter 5

Recruitment

There’s a reframing in hiring that is really helpful to consider this frustration. It’s describing the importance of hiring a great person for the role, rather than hiring the best of the people we meet in the recruitment process. This works in both directions. When an amazing candidate comes along, you have to jump on them and back yourself. And if you’re interviewing lots of candidates and none of them are at the level you need, it’s far better to hire no one rather than the best of the bunch. The comparison effect in hiring also rears its head when there isn’t enough clarity on what makes a great candidate for this role. There are a couple of ways to counter the need from a hiring manager to meet other candidates following an exceptional interview: 1. Current team: If the role is not a new role, and there are already existing team members doing the same or similar roles, ask the hiring manager to compare the candidate against their high performers. If they can see the candidate on par with someone in the team who is excelling, they are more likely to want to avoid any risk the candidate drops out due to delays. Similarly, you can ask them if they’ve hired this sort of role in other companies in the past which can be helpful if it wasn’t too long ago. 2. Grouped interviews: If the role is a new role for the team or company, it’s helpful to group the first couple of interviews together to counter this exact risk. This requires some planning at the shortlisting stage, but it reduces the likelihood you end up with an outlier candidate who is at an opposite end of the process to all other candidates.

73

Chapter 5

Recruitment

3. Role description: If you’re finding yourself in the situation where it isn’t possible to group them together and the interview has happened, it’s worth going back to any notes from the briefing or role description to where the hiring manager described the candidate profile they’re looking for. In this case, you can use these conversations as a quasicomparison of the candidate to the success profile. 4. Keep the ball rolling: If all of the preceding ways fail, tactically, it’s best to keep that candidate moving through the recruitment process rather than delay until other interviews are held. In this case, it’s worth checking with the candidate where they’re at in other processes, and aim to book the next stage a few days or a week out to allow a bit more time for other candidates to reach the interview stage. This doesn’t solve the comparison needed from the hiring manager, but it does help play the cards you’re dealt. In the next chapter, we’re going to tackle a topic that is never short of strong opinions, varied practices, and a whole lot of complexity. So it should come as no surprise that the mental notes I have taken, and continue to take, on this topic are full of mistakes, lessons learned, and a few pointed observations. Let’s talk Reward.

Summary •

74

So many parts of the hiring process are broken. We have an opportunity to do good by people and offer up a candidate experience with care, speed, and respect at its core.

Chapter 5

Recruitment

•

Best offer first principles can drive tangible results and reduce asymmetric information in the offer process.

•

Reframe hiring to be about hiring someone who is a great fit for the role, not hiring the best person from the candidates you’re interviewing.

•

Demonstrate two-way interviews by turning the tables.

75

CHAPTER 6

Reward In this chapter I’m grouping together all things compensation, equity, and benefits into the catch-all that is reward. And, if we’re joining a startup, our first interaction with reward would have happened right at the start of the last chapter on recruitment (hopefully because of pay transparency!). I spend a lot of time thinking about reward, and in companies of all sizes too, not just startups. It’s an area I’ve made a lot of mistakes and felt like I’ve been continuously iterating, and as I alluded to earlier, even after over a decade of working in and around the reward space in companies, I definitely do not feel like an expert. For this chapter, I’ve selected some of the most powerful lessons I’ve had to learn along the way in a startup environment. It’s a topic that is deeply strategic given its financial impact, very difficult to reverse decisions, and is heavily linked to our psychology, emotions, and wellbeing. There is no other part of the People space, or any chapter in this book, that has a greater span of outcomes on the business than reward. When we get it right, it’s a game-changer. When we get it wrong, it’s destructive.

Design for the 99% The saying “don’t design policies for the 1% of people who abuse them” or words to that effect has been floating around People circles for years now. It’s a fundamental mindset shift to what the previous decades of HR

© Patrick Caldwell 2023 P. Caldwell, People Ops, https://doi.org/10.1007/978-1-4842-9819-0_6

77

Chapter 6

Reward

practice have taught us. Protect the business. Manage risk. Mitigate edge case scenarios. And we’ve ended up with policies, contracts, benefits, and programs that have so many restrictions and clauses that the average employee feels like a child. In the benefits space specifically, having too many restrictions in place just in case the odd employee tries to abuse it very quickly discourages others from using the benefits in the way that they could. It’s a careful balancing act as, on one hand, there will always be someone who will be devious and push their luck and you can’t ignore that, but on the other hand, the more trust and freedom you give your people, the more they will value and utilize the offerings in front of them. Here are a couple of ways to build for the 99% and rethink benefits in the workplace.

Learning Budgets We’re making a needed transition from company-provided training to the concept of each person having a learning budget to invest in their development. Learning budgets help us to think more broadly around our development and have flexibility with the type of development too. Not everyone learns by going to a conference. Having implemented learning budgets now a few times, there are a couple of watch-its that can enable or hinder success: •

78

Put the learning budget in the hands of the learner: If the learning budget is a line item on a spreadsheet and I need to submit an expense claim or request for an activity to be paid, I’m putting barriers up for people to use it. Expenses assume I have the funds to pay for something and wait days or sometimes weeks to be reimbursed, which is not the case for a lot of people. Similarly, if I have to request for an item to be paid for

Chapter 6

Reward

by the company, I’m less likely to suggest something that might not fit the expectation for my role (e.g., a customer success representative wanting to complete a coding course). There are dozens of solutions on the market to allocate budgets and payment methods to employees that bypass both of these challenges. •

Use guidelines to help people understand what professional development is: I made the mistake of assuming everyone knew what the learning budget was for. And then I started receiving questions like “can I buy this book on product management even though I’m in sales” and “is it acceptable to use the budget on professional memberships.” So we built guidelines that everyone could see that helped people answer those questions and also think creatively around learning. We included some examples of impactful learning initiatives others had invested in, but also addressed things we wouldn’t accept so people didn’t have to ask what they thought might be a silly question.

•

Remove approvals and process to the absolute minimum you need: This is really about trust. I’ve implemented both zero approval budgets where complete trust is provided and, as I write this, have just implemented a £100 limit for a new learning budget we’ve launched (as a compromise with a view to removing all approvals once we show it’s being used the way we intended). The zero approval budget was designed to build trust with our people. We trust you to identify, invest in, and complete professional development activities without the police watching. Does it mean that someone bought an iPad once as a “learning activity” and we had 79

Chapter 6

Reward

to arrange for a return and refund… admittedly, yes. But it also meant over 5,000 other orders were placed that were completely in line with our guidelines. And that statistic is worth way more to the business than the 1%-er. •

Share share share share share: Learning is infectious, so whether it’s through specific forums or communication channels, or built into a tech platform you’re using for learning budgets, create a space where the team can share what they’re learning, or hoping to learn, and nurture that curiosity and community.

Parental Leave Those who’ve worked with me in the past know this is something I have quite passionate views on. The current state of play will differ by country, but I’ll broadly generalize as statutory leave provisions that do not reflect modern families, and company parental leave policies where parents have to put a few hours aside to work out what they can and can’t do. I’m not a parent and probably won’t be, and admittedly I have worked on my fair share of traditional leave policies and believed the reasons around me why a parent can’t access it in their first 12 months, or if they don’t return for 12 months, they have to pay it back. What changed my perspective were the very people it set out to support. Parents. The more time I spent with parents, the more I realized it was a company policy designed for the company, not for the parents. I would speak with mothers who had delayed a decision to start a family because they weren’t entitled to leave yet. I spoke with fathers who desperately wanted to spend time with their new family addition and were told they get a week off or need to take all of their PTO. And I spoke with same-sex, single parent, and adoption-based families who struggled

80

Chapter 6

Reward

to navigate policies that were never designed with them in mind. An overwhelming pattern I found across all parents, regardless of gender, circumstance, or location, was the need for parental leave to provide meaningful time with their new child. Every company will have a different appetite around parental leave, different statutory requirements by location, and different budget constraints too. The baseline I have found myself coming back to in multiple startups might be a helpful starting place to consider as you look to engage and support your parents and would-be parents. •

Leave: Meaningful and fully paid. I’ve used 12, 16, and 26 weeks of fully paid leave at various companies and also considered additional pro rata pay and the ability to carve up that leave (i.e., 24 weeks at half pay rather than 12 weeks at full pay might be a preference of some parents).

•

Gender-blind: There’s a shift from maternity/paternity/ adoption policies to primary and secondary caregiving policies, and even further to gender-blind. I am in the latter camp and making leave and support available equally to all parents, regardless of both gender and family circumstances.

•

Global: Human beings love to compare and, if you’re a global team, you’ll have folks looking across the fence at what benefits are being offered elsewhere. Unless there’s a really compelling reason why a parental leave policy can’t scale globally, I’d highly encourage one offering globally.

•

Flexible: Not every family needs one or both parents having big lumps of leave the way we think of parental leave. Sometimes it makes sense for extended periods 81

Chapter 6

Reward

at a lesser entitlement, or the flexibility to stop and start it. Being able to take the statutory minimum and then having the flexibility to take chunks of leave within one to two years rather than all at once can be super helpful for people, especially if there are considerations around caring arrangements. •

Accessible: My favorite one so I kept it to last. It’s not easy getting everyone on board with this (I certainly haven’t been successful every time), but I fundamentally believe it’s the right thing to do. Accessibility means removing the tenure requirement and removing clawback provisions. Parents do not need more barriers up against them and these are risk-based policies that play to the 1% of people who abuse the offering, not the 99% of people who do not. Accessibility and autonomy are critical when a family is expanding, and I count on one finger the number of times it’s been taken advantage of (out of 50-ish, which I guess makes it the 2% rule).

Pay Transparency Pay transparency has been one of the most hotly debated issues in the reward space in the last five years. The status quo for too long has been to accept the power dynamic where employers have asymmetric information and advantage to control a pay conversation. Between reward frameworks, market data and benchmarks, budgets, and internal pay knowledge, it’s a steep mountain for a candidate or employee to climb to reach a point where they feel their pay is set with clarity, fairness, and reflective of their experience and performance.

82

Chapter 6

Reward

There is no silver bullet to this, just a long line of candidates and employees hoping for change. For a more level playing field. To start day one confident, they are being recognized for what they bring, rather than feeling a bit weary after a fight. One of my favorite parts of startup life is the ability to experiment, analyze the impact and results, and iterate. The ability to enact change when there’s not a huge amount of embedded structure already isn’t easy, but it’s easier than established organizations without the same freedom to experiment and iterate. And, if the results are poor, the ability to roll back the changes. For this reason, I think startups are a fantastic place to explore the concept of pay transparency and how we take it from a “nice to do” concept for the most progressive organizations, to a “must-have” forming part of every company’s social license to operate. In practice, it’ll probably form part of a legal license to operate in most locations soon anyway. On several occasions, I’ve shifted recruitment processes at startups to include transparent salaries and benefits. For some roles like a People Advisor, it means putting salary ranges like $70,000 to $80,000 on the advertisement so that all candidates have that information before they apply. For roles where variable compensation exists, it means putting the total cash compensation like $60,000 to $65,000 plus $60,000 ontarget commission, or plus 10% bonus. For good measure, I’ll usually ask for salary expectations, if they have them at this stage, as part of the application. Note, this isn’t asking for salary history and there are enough documented reasons now why we shouldn’t ever do that, but in this case asking for expectations back makes the first stage for those who progress a very informed conversation on both sides to check for alignment. Pay transparency discussions bring out the best questions, so for the rest of this lesson (that I’m still learning and implementing!), I wanted to share some of the best questions to help get under the skin of the merits of pay transparency.

83

Chapter 6

Reward

Will I miss out on applicants who don’t fall within that range? Possibly, but it’s likely to be far outweighed by what you’ll receive through transparency and there are ways you can prevent applicant leak at the application stage. If a candidate’s expectations are less than the range you’ve provided, they’ll self-calibrate and likely reset their expectations in line with the range. It’s really hard for candidates to know how to price themselves in the market so consider this a gift. If a candidate’s expectations are higher than the range, you’ll see one of two things happen. They’ll still apply and either make known in their application that their expectations are higher, or just state expectations are at the top end and wait to learn more about the role before sharing their original expectations. Or they’ll choose not to apply because the pay doesn’t meet what they’re looking for. This is OK for some candidates and might show a misalignment between the level of the role and the level of the candidate. A helpful tactic is that below your salary range, you can use a statement like “If your salary expectations are above this range but you think you’re a great fit, we’d love to see your application and discuss with you your alignment to the role and what options we might have available to make it work.” It’s possible there are other levers to pull around benefits, equity, growth opportunities, etc. What if the salaries are more than what we pay the current team members in those roles? This comes up more than I wish. The key here is why the salaries are different. If the role is genuinely positioned higher in terms of the level of experience and skills the expected employee will bring, that’s a very valid reason for paying more than existing team members. The key here is for the manager to be transparent about this before you go out to market and address any questions. In my experience, their future teammates are almost always very understanding of the reasons and just don’t want to miss out on the opportunity to grow and increase their pay too.

84

Chapter 6

Reward

If the salary is higher because the market has moved and your pay range has increased as a result, or if the existing team is below the current market rate regardless of the reason, you have a more fundamental problem than pay transparency. This points to an area of your reward framework or cycle that hasn’t synced salaries with market rates quick enough to catch up to market. It poses a choice. Do you include the pay range and risk upsetting your current team, or do you hide the pay range and disadvantage candidates applying for the role? If those are the only options you are willing to consider, it doesn’t matter which one you choose. Both do damage, although hiding the pay range is probably the less risky business decision to avoid heightened risk of churn. Just know though, once a new person starts, everyone in the team will eventually know the salaries of everyone else. Transparency either happens by design, or by human behavior. There is a third option, which is to tackle the more pressing issue to enable pay transparency. There’s a rough and ready way to tackle it and a more comprehensive way, so if time is a priority and you’re in “that” sort of startup, rough and ready might be worth a look. The rough and ready way is to make market adjustments for just the team or roles directly impacted. If you’re hiring a Front End React Developer, it means all Front End React Developers who are too far below market based on the ranges you have. There is possibly a more systemic problem affecting other teams, but the focus here is on fixing an issue you’ve found and keeping the hiring engine going. Once the market adjustments are in, you have the ability to share the pay transparently on the job ad and continue on. Another way to look at this is this – if you discover your team is paid below market, your competitors are going to be using the higher salaries when they reach out to your team to pitch them opportunities. So even if you hide salaries from the job advertisement, you’re opening up your team to a significant reason why someone would take another opportunity and leave. This is why it’s so important to lock your team in. There’s no point focusing on hiring if there’s a revolving door within the team.

85

Chapter 6

Reward

The more comprehensive issue is to go back to the framework and cadence for reviews to see where it slipped out, and assess possible impacts across other teams too. These sort of things happen all the time throughout reward cycles, so we need to be comfortable with iterating. In the example with the developer earlier, if you’ve rectified that team, the review of other teams can happen simultaneously and should probably start with the highest risk areas of the business (those in hyper-growth mode or those that have skills identified as in shortage in the market). How big of a range can I put on the job advertisement? When pay transparency laws started to be passed through a number of US states after the pandemic, we saw the rise of pointless transparency. Companies, being forced to now comply with pay transparency laws, choose to set the range so large as to be pointless and of no benefit. I remember one infamous one for a software engineer where the range was $500,000 wide. Pointless and a waste of everyone’s time. Admittedly, there are some roles where the range can be difficult to keep narrow especially if you’re setting a total compensation range and including things like variable compensation, commission, and the value of equity grants. If you’re advertising across multiple geographies and set pay based on the local market, including a single range, covering multiple geographies will also usually mean a very wide salary range. As a rule of thumb, if I’m only posting base salary on the advertisement and in a single market, I aim to not exceed a 20% range. A bit of creep isn’t harmful, but when we start seeing advertisements for $60,000 to $120,000 for roles, no candidate is looking at that and feeling informed or impressed. Where advertisements cross multiple markets, make it transparent that this is the reason for the discrepancy, and use a location at either end of the scale to help people understand where they can likely position themselves. Again, without this sort of detail attached to the salary ranges, it’s near impossible for candidates to consider if it meets their expectations. 86

Chapter 6

Reward

And finally, where multiple compensation components are included, don’t just lump it together into a huge range. There’s a huge difference for a sales rep seeing an advertisement saying $120,000 OTE compared to one that says $80,000 base salary plus $40,000 OTE commission. Split out the components so candidates can understand what’s on offer and make an informed decision on whether they are throwing their hat in the ring. What about transparency of the current team’s salaries? This is an area of pay transparency that is truly fascinating, and muddled up in sorts of human behavior and personality too. One approach that some companies have taken is to take pay transparency to the maximum level possible and publish the salaries of their team either internally or externally, or both. The question has come up from the team a few times in startups I’ve been part of, and for me, the reasoning behind it can be really helpful to understand.

“I want to know if I’m fairly paid compared to others?” “If we’re trying to be more transparent, why wouldn’t be just be transparent about this?” “You can’t fix what is hiding in the shadows.” There’s a lot tied up in that sort of reasoning, and all things I’ve heard as part of why you’d take transparency to that level. It was also coupled with counter opinions around people feeling uncomfortable having their own salaries being shared, and people not wanting to know salaries of others too, all of which is also a consideration. I have no doubt there are some businesses who have infused a radical level of transparency into their culture from day one. This level of salary transparency makes a lot more sense when done from the start, as it then represents the business that every future new joiner has chosen to be part of. I’ve never been able to rationalize, on a personal level, how the preference of one person to have public salaries is more or less important than another person’s preference to not have public salaries, unless there’s an opt-in where people can choose to share their own only. 87

Chapter 6

Reward

There aren’t too many lessons in this book where I don’t share a strong opinion, even loosely held ones, but this one fits into the bucket of things I feel conflicted and undecided on. The test I want to now apply the next opportunity I have is if you have a robust salary, role, and leveling framework across the business and make it transparent around what roles exist, what is expected of each role at each level, and the salary ranges the business have set for each role and level, is the rationale for public salaries still there, or has it diluted because transparency of design and decisions has fulfilled some of the original concerns?

The “Pay Me More or I’ll Leave” Ultimatum It’s a people issue we never want to happen, but we’ve all probably had it a few times. A team member asks to speak with you, has an offer on the table at another company, and is using it to negotiate a pay rise. I received an unexpected but very real insight into how we end up in this situation from a friend and former colleague. We’ll call her Sam. Sam’s story isn’t something that happens every time, but sometimes in the People space, we can feel attacked by these ultimatums and feel a bit bitter. I’ve certainly been guilty of that. So I like Sam’s story for a number of reasons, as you’ll soon see. Sam had tried to have a conversation with her manager about pay on the basis of her performance and having not had an increase in almost two years. Sam’s manager had said to her that she needed to back up the request with data to prove why a pay increase was appropriate (I’m not going to tackle this problem, but you’re probably thinking the same thing I am about the manager at this point). Sam pulled together as much as she could around what she had delivered, and also grabbed a few salaries from Glassdoor as a comparison. She went back to her manager, but no luck. This time, the manager said the Glassdoor salaries don’t justify the pay rise but her performance had been strong and she’ll be considered 88

Chapter 6

Reward

for a pay rise at the end of the year which was still over six months away. Sam enquired about bringing forward the pay rise and was told only exceptional cases are considered by the HR team and this wasn’t exceptional. So, Sam started looking elsewhere and ended up with two job offers (Go Sam!). She didn’t really want to leave but she would if she felt her performance wasn’t reflected in her pay. Sam spoke with her manager again, this time referencing two offers and asking for it to be raised as an exceptional case for review. She was then invited to a meeting with the HR Business Partner and was told they don’t respond nicely to ultimatums, that her pay wouldn’t change, and if that meant she will resign, then it would be a shame. There was also some guilt-tripping from the HRBP about how the workload for the rest of the team would increase if she left but I’m parking this under HR behaviors I wish would die quickly. Sam resigned and is now earning more money elsewhere and, last I checked, is really enjoying her role and team too. I really felt for Sam through this process. She kept having barriers put in front of her and ended up using the ultimatum as a last effort to show how serious of an issue it was for her. The going belief in the HR and People profession is to not give in to ultimatums as they’ll probably leave anyway. Some people probably do. But some don’t. And it’s our job to navigate the scenario enough to understand what sort of judgment we apply to this, rather than the blanket approach to not give in. I know I’ve fallen into this trap, and there are a couple of ultimatum conversations in the past that I wish I could replay, and a few tips and lessons I’ve swallowed along the way.

Mitigate the Likelihood of Ultimatums I’m a big believer in the concept of stickiness. Identifying and investing in the reasons for each individual that makes the business a very sticky fit for them. When the stickiness wears off, it opens up the risk that they 89

Chapter 6

Reward

find a stickier fit elsewhere. In the case of ultimatums, our first priority should be to reduce the likelihood someone feels that their pay doesn’t reflect their role and performance. This means regular reviews of roles, performance, and pay, a clear link between someone’s performance and achievements and pay increases, a close eye on external conditions that affect cost of living, and perhaps most importantly, coaching managers to have proactive and candid discussions with their team members about pay.

When We Get Pay Wrong Some ultimatums are because we simply got it wrong. We’ve let our team member down, either through not keeping up with the market or not ensuring their performance, skills, and contribution to the team are reflected in their pay. When these ultimatums happen, there’s an opportunity for us to make it right, but it’s important to do that sensitively too and consider the full picture. If it’s clear that we got it wrong and we’d like to try and make it right, it’s worth asking your team member if there are any other things on their mind that would improve their experience at the company. It could be growth opportunities, relationships within the team, feedback, recognition, training, tools, and the list goes on. The reason why this is important is that if the belief around quick turnover after agreeing to new pay is true, the reason why they leave is less likely to be pay rather than something else. Sure, it’s possible a competitor puts a massive offer on the table and they accept, but that’s an uncontrollable factor. Typically, quick turnover after negotiating a new pay is because something else has prevented stickiness, so you may as well know about it now and work through it than find out later.

90

Chapter 6

Reward

When We Don’t Get Pay Wrong The scenario earlier of a competitor tabling a massive offer is a good example of this. Some ultimatums are simply out of reach, either because the other offer is well outside of the reward framework that there genuinely isn’t a budget available for it, or it risks severe disparity with the rest of the team (i.e., don’t create another problem by solving a problem). When this plays out, the situation can feel more complex and the risk of churn much higher. I’ve had this a couple of times, and it’s not uncommon in tech companies for some mammoth competitor offers to lure away in-demand skills. This is typically where I don’t agree to the ultimatum and accept we’ve lost someone, but it’s not the starting point. In these situations, it’s worth exploring how they’re feeling about other parts of their role, such as the stickiness factors we discussed earlier, and if you were to table something that gets you part of the way there and consider changes in other items raised, whether they’d be open to considering this. I cannot stress this “watch it” enough. Team pay parity is sacred and should be nurtured. It doesn’t mean things need to be equal, because they shouldn’t be, but parity of reward outcomes that are transparent, with clear links to performance, and building a sense of trust and fairness within the team. Team parity should almost always outweigh individual outcomes.

The Law Is the Floor When I was studying for my HR qualification and throughout my first few years in the field, I was under the impression that the laws in each country determined what people received by way of benefits. If we’re only talking about legal entitlement, then indeed they do. But in many countries, the statutory entitlements under law leave a lot to desire. It’s what you have to do, not what you should do.

91

Chapter 6

Reward

If you’re a global startup, it also means you’re keeping an eye on the laws of all countries you’re operating in and navigating the need for compliance and consistency. It wasn’t until I entered a global environment that it became more obvious of the need for us to have a global position on benefits designed for our startup and consistent across the team. Take something like maternity leave. Depending on the country, statutory maternity leave can vary from unpaid leave only to six months’ leave at full pay, to twelve months leave at statutory pay rates. Navigating all of that individually is complexity that your People teams and managers simply don’t need. The way I’ve tried to look at the law is as the bare minimum you must do. The law is the floor. And there are actually very few statutory entitlements that you’d argue are best practices in themselves.

All Benefits Are for Day 1 The hiring manager calls you after a final stage interview and offers you the role. You’re over the moon. They share with you how impressed they are and excited by what you’ll bring to the team. You turn up on day one, pumped to start onboarding, and get stuck in. You finalize all of your payroll forms and start reading up on benefits. You need to work here for three months before you can enroll in retirement benefits. Three months before you can access your learning budget. Six months before life insurance cover kicks in. Your probation period before you’re eligible for a bonus. Twelve months before you can access parental leave benefits. For a company so excited by what I’ll bring to the table, they seem to be hedging a lot of bets if things don’t work out. You sit back in your chair, curious as to why they are confident enough to offer you a job and pay your wage, but not so confident as to give you the full package until you’ve hit a certain timeline.

92

Chapter 6

Reward

The tenure requirements we’ve put in place around benefits are a total misfire. Remember the 99% lesson from earlier in this chapter? This is a prime example with some unfortunate side effects. When new team members come in, they are already eager to impress, and likely a bit anxious and cautious too. We need to be doubling down on our support of, and confidence in, them to succeed and achieve. Trying to mitigate some admin or a bit of cost if things don’t work out sends the opposite symbol. It says we aren’t yet confident in you to receive access to everything. We have to go all in on our new team members, which means all benefits from Day 1.

 ou Probably Won’t Retire Early Because Y of Equity We need to talk about equity. If I do a second edition of this book in the future, we’re going to split out equity into its own chapter as it’s quickly becoming one of the most complex parts of startup compensation to navigate. Some companies nail it. But most I’ve come across struggle to get it right. I’ve seen a fair number of share and option frameworks to date, and I can’t say any of them truly nail it. It’s become a personal endeavor to keep iterating and finding ways for equity to play the role it can in people’s experience. One of my first ever introductions to the world of startup equity was from a friend who told me the plan was to exit in a few years and retire. My first thought was “Hell yeah!”. At the time, he was an employee at a seedstage startup and took a sizable haircut to his previous compensation to take a meaningful equity stake. An all too common story, and a decision I wholeheartedly support and respect from anyone wanting to get stuck into building while the startup is still a garage band.

93

Chapter 6

Reward

It turns out he took a 0.5% equity stake and, in his mind, he would sell it in the future when the company became a unicorn (i.e. worth $1 billion). “I can live off that for the rest of my life.” It didn’t click at the time because I was a novice in the world of startup equity. Like 99.5% of other startup employees, my understanding of equity didn’t extend beyond understanding the general concept of shares and options, and that if the company is sold or listed in the future, I could get a payout. What my friend experienced was equity hype. A combination of the leaders of his startup allowing unrealistic expectations and an excitable recipient who started believing, even planning for, the best possible financial outcome that might just come from an exit. Over the course of several startups and now over a hundred conversations with startup employees about equity, I’ve ended up with a long list of things I’ve had to learn along the way and, in some cases, have a brutal reality check on. Here are some of the most pertinent.

E quity Requires a Framework More Sophisticated Than What We Use for Salaries In the early days of a startup, founders and investors are likely picking and choosing people to receive equity grants. It’s usually a mixture of early-stage employees (very common up until 20 or 30 people given cash constraints) and others they want to recognize and retain. It’s not uncommon for this to be very unstructured. Discretionary decisions, discretionary allocations, sometimes even discretionary terms of the agreement depending on what the relevant equity scheme allows for. As the startup grows, greater consideration is given to the size of the equity pool by shareholders and investors, especially if the startup is investor-backed and likely to go through rounds of funding in the future. The equity pool is an agreed allocation of a percentage of the company for employee grants and can be dilutive to existing shareholders. Over

94

Chapter 6

Reward

time, and as the cap table changes, the equity pool is revisited and sometimes resized to take into account future headcount growth and new employee grants. At the same time as this, the startup is growing into a scale-up environment. Roles are becoming more specialized and defined, teams are starting to take shape and consider their own structure and operations, and the People team (hopefully in place by now) are looking at the infrastructure needed to grow, such as scalable reward frameworks, performance management, engagement and feedback mechanisms, and progression. These changes to both the governance and operations of the startup, and the headcount growth, both call for a more sophisticated approach to equity in the same way we’d be maturing the approach to compensation or other areas. The reason equity requires a more sophisticated framework than we might be hoping for is how fluid the equity environment is. Valuations may go up and down over time. Early-stage employees often receive larger equity grants than later-stage employees. And it can be difficult to quantify the value of equity you’re awarding on a consistent basis. An employee receiving 100 shares at a $10 share price is the same value of equity as someone who joins and receives 50 shares when it’s a $20 share price, but at that stage the value of the first employee’s equity has doubled. There are four scenarios I try to make sure are built into equity frameworks to allow for the majority of considerations as we grow. More recently, I’ve found answering these four scenarios will flesh out a lot of the thought and consideration required when building an allocation framework. 1. New hires: What do we award by role, level, and geography and have we modeled the one- and two-year growth plans and headcount against the framework and equity pool?

95

Chapter 6

Reward

2. High performance: How do we use additional equity grants to reward high-performing team members and build more stickiness? Similarly, if high performers take on more responsibility and bigger roles, there may be equity implications too. 3. Tenure/retention: This may be more or less important depending on how equity vests and how it can be exercised. But if you’re running the standard fouryear vesting and one-year cliff model, how do we top up those when vesting ends to ensure there is always equity continuing to vest (i.e., stickiness again!)? 4. Leavers: How do we deal with leavers taking into account equity pool sizing, the need and ability to exercise, and sometimes the tax implications in the employment country?

Understand the Risk and Likelihood of Dilution If you’re in a startup without investors or a need to fundraise, this may be of less consequence to you, and it’s probably another huge selling point to the value of bootstrapped businesses who don’t nearly feature enough in the technology press. If you’re in an investor-backed startup with equity and have fundraising on the horizon, you need to understand dilution. If you haven’t come across dilution before, it’s essentially the process where the percentage of shares you own decreases as a result of new shares being issued. So let’s use the preceding example again.

96

•

There are 1,000 shares in the startup, with a share price of $10 per share, making the startup valued at $10,000.

•

You receive 100 shares which puts the value of your equity at $1,000.

Chapter 6

•

This means you own 10% of the equity in the company.

•

Your startup does well and decides to take on a round of funding to fuel the next stage of growth. An investor purchases 200 shares at a share price of $20 each, making a total investment of $4,000. Unless existing shares are being sold, these are often added as new shares (see the next note on preferences).

•

There are now two things you should be aware of: •

A share price of $20 each means your equity is now worth $2,000 instead of $1,000.

•

There are now 1,200 shares in the startup (the original 1,000 plus the 200 shares from the investment). This means 100 shares now represents 8.3% of the equity in the company instead of 10%. This is dilution.

Reward

Dilution is very common with startup equity and something to understand, rather than to fear. The reason it makes this list though is twofold: Firstly, my friend who received 0.5% equity as an early-stage employee almost certainly won’t have 0.5% equity if they “become a unicorn in a few years”, unless they’re in a true outlier startup. If you assume an average of 15-20% dilution over four rounds of funding, it’ll be more like 0.2%. That would still be a load of money and congrats to anyone in that situation, but it’s worth being mindful how dilution impacts you. Secondly, dilution feels less important when businesses are growing very successfully. In the example earlier, having 8.3% equity is quickly overshadowed by knowing the value of your equity doubled to $2,000. This is the trade-off considered acceptable for dilution. You can dilute the ownership percentage of shareholders but return a multiple of that in increased share value. Where a business is not growing successfully though, dilution can have a negative effect. Imagine the company earlier raising money at the same share price of $10. The value of your equity is the same, but the dilution still exists. 97

Chapter 6

Reward

Liquidation Preference When an investor or new shareholder comes on board, they may have a liquidation preference or preference shares. This means there is an order, and sometimes a value, determined for where proceeds of an investment go first. Those with liquidation preference will essentially get their money back before those without preference. In some occasions, it can even be a multiple of their investment depending on the terms agreed. Again, this may feel less consequential if a startup is growing really well and there’s a successful exit of some sort. What is helpful to know is that employee equity is typically for ordinary shares and therefore at the bottom of the ladder. A lot of other people will be paid first, and depending on the preference terms, how many different levels of preference exist, and the valuation of the company, the proceeds that make its way to ordinary shares can be less than expected, and even zero.

E quity Is Worth Nothing, Until It’s Worth Something Sounds more philosophical than I mean it. Equity is not cash, or even a bonus. It doesn’t pay the bills. You can’t take an option grant into the bank to use it as a deposit on a mortgage. There is zero guarantee that the value of the shares in your agreement is worth more than the paper it’s written on. I’m sorry to pop the balloon, but it’s time for a reset. Equity is a really memorable and valued thing to receive as a startup employee. It allows future success to be shared. It might even start to make you feel a greater sense of ownership over results, or think through problems and opportunities in different ways. I hope that everyone who receives equity either has it structured to allow for exercise and sale processes to happen in a way that the employee sees value to their equity, or gets to experience an exit event of some sort where the full proceeds

98

Chapter 6

Reward

are realized. The reality, however, is that very few people see either of these things in a startup. Some do, and their stories tend to spread and be shared. But most don’t see any value to their equity for a variety of reasons. So if you’re holding on to a share or option agreement, I truly hope you see value from it, but it’s important to make sure you’re comfortable with the fact it may never happen.

Minimum Leave, Not Unlimited Leave If you were on LinkedIn around 2016 and scrolling down your feed, you would have been met every second or third scroll with another company posting about how they’ve given their team unlimited holiday leave. To date, it’s certainly become more common than other initiatives having their time in the spotlight. Unlimited holiday is a pretty interesting concept. The first time I heard of it, I cheekily asked if I could take the whole year off because I had unlimited holiday. Now, before I take aim at unlimited holiday, I really do like the rethinking of holiday leave to be built around concepts of wellbeing and trust, rather than leave entitlements. The thinking behind it is centered in creating a great people experience, so big kudos to those thinking this way. On paper, unlimited holiday is exactly that. We ask for our team to take time off when they need it, communicate well with the team, contribute to team planning and coverage, and not feel the pressure that comes with an annual holiday entitlement. In practice, unlimited holiday means we’re OK with you taking a bit more than what you’ve come to expect as your entitlement, but not so much that we think you’re abusing the benefit. The only difference with the latter is you’ve now moved the responsibility and pressure of knowing what is acceptable and what isn’t acceptable to your team member. It’s up to them to work out the norms and restrictions, which usually don’t become explicit until someone steps on the wrong side of what is acceptable. 99

Chapter 6

Reward

There’s enough research now into unlimited holiday to suggest that, on average, people take less holiday than what they did when they had a clear entitlement. Which makes sense given the pressure has shifted and most team members don’t want to do wrong by their manager or their team. This behavioral impact is merely a hiccup, and I don’t think the merits of unlimited leave are lost. The principle of trusting the team to look after their wellbeing and take time as needed is exactly what we want within more workplaces. But without some sort of guideline to what is expected, it’s hard for this to eventuate. For me, I’ve landed on a reframe of unlimited leave to something that aims to balance the principle of trust, alongside creating safety for people to be trusted to look after their wellbeing. It involves setting the minimum and maximum for leave. The minimum might be company policy or a statutory requirement, so let’s say it’s 20 days. And the maximum is what we actually accept before we start to think someone isn’t working enough. So let’s say 40 days. The new holiday leave policy becomes “We offer up to 40 days of holiday leave, with a minimum of 20 days each year to make sure you’re recharging enough” or something similar. I think that means we can’t call it unlimited holiday anymore which takes some shine from it, but I’m OK with that! This chapter likely felt heavier than other ones which is to be expected given the complexity and sensitivity of reward. In the next two chapters, I’m sharing principles and lessons learned in Learning and Performance, two parts to the People experience that go hand in hand in terms of developing our people, but require their own techniques and approach.

Summary 1. Build benefits for the 99% of people who will benefit from and value them, rather than the 1% that abuse them. 100

Chapter 6

Reward

2. The status quo of hiring without pay transparency has passed its expiry date. We need to prevent asymmetric information and an employer-dominated power dynamic, and reduce the inequities in pay discussions that prevent our people from feeling recognized, valued, and fairly treated. 3. It is not black and white to simply say no when someone poses the “pay me more or I’ll leave” ultimatum. There are reasons why it’s sensible to counteroffer and scenarios where it doesn’t make sense, but primarily our goal is to reduce the likelihood from it happening in the first place. 4. Our statutory obligations for benefits and leave are not our benchmarks for good practice. They are the bare minimum we have to do and there’s almost never a compelling reason why we’d ever want to only do the bare minimum for our people. Similarly, to instill trust into the relationship with new joiners early, avoid tenure restrictions on benefit eligibility. 5. We need to bridge the knowledge gap on all things equity, setting realistic expectations, communicating the key components of equity, and allowing our people to have access to a transparent and meaningful way to share in the business’ success. 6. Unlimited leave may seem sexy, but it often proves to have a negative effect. If you do want to rethink leave entitlements, at the very least, it should have a minimum amount of leave that allows for both adequate well-being rests and meets any regional requirements. 101

CHAPTER 7

Learning This chapter continues our exploration of key components or milestones that allow us to engage, develop, empower, and recognize our people. Learning is undoubtedly one of the biggest reasons why people join startups, especially if they are transitioning out of bigger and more established businesses. But learning doesn’t just happen in startups. It takes a whole lot of planning, feedback, design, onboarding, and leadership support to enable learning and the growth culture associated with it, which is what we’re going to dive straight into.

Water Your Plants “We don’t really do much formally by way of learning and progression because we’re a startup.” Yawn. We’ve all heard it. I’ve even said it a few times. The excuse wears thin quickly and it’s detrimental to everyone in the team. In what is becoming a real theme throughout each chapter, half the trick in startups is knowing when to build out a part of the people infrastructure and how to make sure it’s aligned to the stage of the business and the performance and objectives of the business. I’ve always been curious about the return a startup receives from investing in the learning space. It feels intuitive, but I can’t shake some skepticism. I can throw thousands of dollars, and I do, at learning budgets and watch as people buy books and subscribe to online courses, but should I be thinking of those thousands of dollars as an investment that pays back

© Patrick Caldwell 2023 P. Caldwell, People Ops, https://doi.org/10.1007/978-1-4842-9819-0_7

103

Chapter 7

Learning

(and how would I know that), or just treat it as a benefit (which also pays back in its own way, but for the purpose of this I’ll treat it as spend in a simple form). Similarly, I’ve taken part in week-long leadership summits where I sit in a classroom and take in a whole bunch of content and set plans for how I will use it. Oh, and don’t forget the role-plays. They probably cost between 10k and 15k a pop, and outside of the connections and relationships, I can’t for the life of me tell you something specific that I did differently in the workplace and the impact that has on my or the business’ performance. Each time I’ve joined a startup, there are parts of learning that always make it on to the road map. Onboarding, progression frameworks, manager development, technical training, and the list goes on. All important stuff. But the more I work on learning programs and initiatives, the more I find myself thinking about goals and outcomes. The ultimate goals and outcomes. Because I don’t think any of those learning initiatives are actually the goal, but rather the tool or enabler for what we’re actually looking for. When I sit in exec or board conversations, very rarely do we talk about learning specifically. We’re talking about productivity, culture, engagement, retention, and preparation for our next stage of growth. That’s more indicative of the outcomes we need rather than what learning quickly becomes, which is a series of completed projects and some feedback surveys. With this in mind, there are some common pillars that seem to sit in between what we do in the learning space and the sort of outcomes we’re trying to achieve. This is not a playbook, or even a recommendation. It’s just an observation after a few startups and even in larger organizations for the things I tend to look for and focus on in the learning space when there’s very little in place already.

Growth Culture In the next chapter, I’m going to cover the concept of startups and team members outgrowing each other. It could easily go in this chapter too, but I think the link with performance is punchier. As companies rapidly grow 104

Chapter 7

Learning

and try to scale, they start to transform and need to rethink a lot of how they operate. Hiroshi Mikitani’s Rule of 3 and 10 has always resonated with me – essentially that everything breaks and needs reinventing as companies go from 3 to 10 to 30 to 100 to 300 to 1,000. In startups going through early-stage funding, you’re likely going to see three or four transformations of the organization in a short space of time. It puts pressure on people to be agile, resilient, flexible, and curious. And it is that specific need to allow people to grow with the organization that I find myself honing in on constantly for how we nurture and develop it. I mentioned learning budgets before and understanding the return on that spend. So it feels natural to now revisit that with a different lens. In three consecutive startups, I’ve introduced learning budgets with some very specific traits around accessibility, community, and trust. I would never argue with someone about the individual return we get on an employee reading a book. But what about an entire product and engineering team using their learning budgets on resources, with time in their work day set aside for learning, recommendations flowing between team members on what they’re learning and what they’ve enjoyed, and managers finding opportunities for them to apply some of the things they were learning about. There’s no price to that, but it’s quite the return. It builds a sense of curiosity, the feeling we’re all continuously learning and trying new things, and a sense of community within the team. All things that are incredibly helpful when we hit the “Rule of 3 and 10” transformations.

Great Managers Tightly coupled with a growth culture are great managers. Managers have a heightened ability to enable or disable their team on every single outcome we previously discussed. They cast a shadow deep into their team structures and even across teams, so if the behaviors and capability are not

105

Chapter 7

Learning

aligned with the culture, engagement, retention, productivity, and futureproofing needed within the business, it’ll feel like inflating a balloon with holes in it. The first step is understanding what great managers look like in each specific business, and even within teams as there can be differences, especially if you compare commercial and tech teams. Some managers will self-assess thoroughly, but there’s some top-down thinking around behaviors in particular that needs input, and some bottom-up thinking from team members around how managers can set them up, individually, for success. There’s a lot of theory out there, but managers are not developed through theory and content. No one ever walked into a workshop and walked out an expert. So I like to think of the content as a prompt. A little nugget or resource that tickles the curiosity of the manager, or a future manager wanting to explore, and helps them take the step to trying new behaviors. And once they do take that step, a whole lot of reinforcement, coaching, and safety to explore how they show up as a manager and how they contribute to what the business is trying to achieve. Everyone wants to be a manager until they are one, because it’s harder than it looks and you never feel capable enough.

Onboarding I guess this one might feel like a strange addition given my reticence to specific learning initiatives. Onboarding gets a free pass through that. Not because we don’t want to create an amazing and personalized onboarding experience for new joiners, but because of its unique influence on productivity, engagement, and turnover. Most of the startups I’ve worked in have been B2B SaaS startups. And one particular onboarding challenge rears its head in every single startup. It’s hot on the lips of founders, it’s tested and analyzed by investors, and it has a direct link with the revenue growth of the company. Sales 106

Chapter 7

Learning

onboarding. The period of time from which someone joins the sales team to the point they are considered fully ramped and productive. It’s one of the biggest risk areas during hyper-growth as to whether a startup has enough ramped capacity to meet its next revenue objective, and depending on the complexity of the product and the sales cycle, the onboarding process can be quite extensive. I’ve picked sales onboarding as a specific part of onboarding not as an anomaly, but rather a really helpful and effective place to start. Onboarding itself has a clearer connection than many other learning initiatives to business outcomes, particularly productivity and having the right talent performing well at every stage of the startup’s growth journey. It’s also a risk area for other areas. Poor onboarding leaves a stench on engagement, which is a great test of culture and team support, and there’s ample research for the heightened risk of turnover in the first six or twelve months of employment. If we nail onboarding, the positive effects compound and feed into the talent, performance, and progression areas too.

L earning Is About Experiences, Not Just Knowledge A few years back, I shared a post on LinkedIn that hit a spot with a lot of people. It went like this:

Things we do and realize later didn’t teach us much: –– Online courses –– Conferences –– Sit in a classroom –– Most networking –– Read books

107

Chapter 7

Learning

Things we do and realize later taught us heaps: –– Work on stuff we’ve never done before –– Practice our craft in different contexts –– Be mentored by someone –– Fail miserably at something –– Have a difficult conversation with someone –– Volunteering –– Work for a bad manager I remember what prompted the post very clearly. It was a series of conversations with people at all levels in the startup I was part of at the time where we were discussing learning. There was a theme throughout these conversations, and after the theme started emerging, it was one I was keen to provoke and test with others to see how far the theme continued. The discussions related to how we learn, both as humans and also in our roles. The team member reflecting on transitioning from a large and highly structured organization to a scrappy startup and the opportunities and challenges it has provided them. The manager who told me how some of the challenges within their team had really helped them reflect on their leadership style and show them how small tweaks to their style could influence different outcomes. The team member who was telling me about their recent volunteering shifts and how much perspective it’s given them on their own life and upbringing. The senior leader who shared several mistakes they had made at a previous company and some of the things they were going to change or be mindful of at our startup when we approached a similar stage. All of these reflections, plus several others, all touched on things that we realize had an impact on us as humans and as professionals. Situations where, at the time, we probably didn’t realize the extent of our learning.

108

Chapter 7

Learning

But in hindsight, these situations made for critical learning milestones that influence how we now behave and perceive things. No one talked about the self-help book they read. Or the conference they went to. Or the online training they were forced to do. It’s not to say we don’t learn something from these and they still play an important part. But if our approach to learning doesn’t extend beyond the traditional knowledge buckets of courses, books, and conferences, we’re only tackling a tiny part of someone’s learning experience. So the next time we’re considering how we can help prepare a highperforming individual contributor for their first manager role, let’s not just stop at some training. Maybe they could start to pair with a manager as part of conversations and observe what they liked and what they would do differently. Maybe they could start with a junior team member for a shortterm project where they take on the manager role and have a chance to experience that before they step into a manager role formally. And once they do take on a manager role, the learning can’t and won’t stop. They will need to experience the mistakes and failures that come with any new role and have safety to explore these and learn from them.

The “Best” Career Advice I Ever Received “If you want to progress your career, do your job well.” This is definitely the book equivalent of a clickbait title. This isn’t the best career advice I ever received. But it’s by far the most memorable. It was much earlier in my career that it was shared with me and it’s taught me heaps, in its own way. I’ll start with the obvious, which is the stupidity of the notion that to progress your career, you just need to do your job well. That’s not the experience of most people, and frankly, it hasn’t been my experience either. It also reads as a stereotype for someone asking their manager for

109

Chapter 7

Learning

a promotion and being told the “keep working hard and we’ll think about it” excuse. I should also point out at this point that while progression and promotion don’t mean the same thing and I’ll cover that off shortly, the context in which this advice was given to me was relating to whether I would be promoted. The reason why it’s memorable is because of what I’ve taken away from it and how impactful it’s become for me. Whether it was ever intended this way I have no idea, but I don’t imagine the giver of this advice might have anticipated the tangents would take it on in the years ahead. And some of these tangents, well, are pretty loose.

Do I Even Want to Progress? Why is everyone obsessed with promotions? Will I still be seen as doing well if I’m just content in my current role? What if I don’t know what I want? All questions I have asked myself a number of times, and I don’t imagine I’m the only one who might feel this way. We have a tendency to assume progress and growth equals promotions. Sometimes it does, but in several of my roles I’ve not had any real desire for promotion. Most of my promotions have… just kind of happened. I have a desire to be good at what I do, and to keep getting better. I have a desire to positively impact people and the world. I have a desire to see my pay increase (who doesn’t?). And I’d say all of these things feel like progress for me. And all of them can happen without promotions. So the conversation I need to have with myself, and my managers, isn’t really one of progress the way we typically define it. It’s one of growth. What can I do, and what support and environment do I need, to grow in my role? What experiences do I really want to have even if I suck at them or dislike them? What is going to get me out of bed on a Monday morning thinking “let’s get it!”? 110

Chapter 7

Learning

Similarly, the conversations and systems I need to be encouraging as a member of a People team need to reflect the diversity of progress also. It needs to be deeper than a framework of roles and responsibilities, even though for some that will be very important. And we need to make sure that growth is incentivized and recognized, even if a role change doesn’t happen.

Underperformers Are Rarely Promoted I originally wrote this as “never promoted,” before realizing that we all know someone who got a promotion that was clearly unrelated to performance. So I’ll try to be more factual and have edited it to “rarely” instead. This is probably the closest tangent to how the original advice was intended, which is to remind myself that if I do want to push and make a case for a promotion, it must be widely understood that I’m performing well in my current role. There can’t be any doubt in the decision-makers’ minds that I’m ready to graduate. The follow-on from this if a promotion does happen is that underperformers sometimes don’t last long in their promoted roles. There are many reasons why this might come about. If someone hasn’t been set up for success, or provided the right level of support, or made the full transition to the new responsibilities, it’s not uncommon for their performance to drop off a cliff. The risk is higher once someone is promoted. It’s a reminder that any time we step into a new role, we should treat it as an entirely new job, just like if we joined a new company. It means a version of onboarding, building role clarity, setting and agreeing expectations, and making sure it is crystal clear for both us and our managers what high performance looks like in the new role.

111

Chapter 7

Learning

 hat Prompts a Manager to Say “You’re Ready W for a Promotion”? When I reflect on promotions that I have done within my team, it’s never just someone doing their current job well. That’s important, but it’s never the only thing. It’s the same thing when I’m speaking with managers about promotions in their team and their mindset to know if someone is ready or not. There are three things that come up regularly that differ those who are high performing and those who are high performing and ready for a promotion or level up. 1. Outcomes: Performance is clearly articulated in terms of outcomes and impacts. It’s not about effort or inputs, but rather the results and business impact as a result of their work. 2. Transition: Often, those receiving promotions have already made some form of unofficial transition. Even if it’s just an inch into the new role, they typically have taken on responsibilities already that are more reflective of the role they are going into. I think this one drives a lot of the confidence managers have when deciding someone is ready for promotion. 3. Making life easier: Our manager’s performance is mostly a reflection of our performance, as individuals and as a team. This is especially true as teams grow beyond a couple of people. A key contributor to promotions is often those people who make life easier for the team, and therefore the manager. Those that proactively identify issues, are introspective to how the team performs and finding ways to be more effective, and who help support and amplify the team of others around them. 112

Chapter 7

Learning

Approach with Planning: Peer Feedback Peer feedback can be a gift and a curse to someone’s development. Rounding out feedback to provide a more holistic view of how someone is performing and growing can be hugely beneficial and also helps to prevent the impact of manager bias slipping in too. So when the feedback is specific, meaningful, actionable, and nonjudgmental, the addition of peer feedback can support both self-awareness and someone’s actions toward development. So, what’s the issue then? The risk of peer feedback is the higher likelihood that it is not specific, meaningful, actionable, and nonjudgmental, unless a significant amount of planning, upskilling, and expectation-setting is completed. In my experience, it’s seldom devious, but rather has a tendency to fall into a few traps that hinder it being useful for the recipient. Here are a few things I’ve learned from implementing peer feedback mechanisms.

Giving Feedback Is a Skill It’s hard to provide feedback more meaningful than general praise. And we often don’t really know the specific areas our peers are looking to focus on, or the journey they’re going on too. It’s very common with peer feedback for people to provide a list of general things they appreciate about someone, such as them being a great team player or being happy to answer questions for others, and if prompted to discuss how someone could improve or where they should focus, we slip into “nothing comes to mind” or “keep doing what you’re doing” feedback. For this reason, I try to invest a lot of time up front helping people think through and structure feedback based on specific observations, and discourage feedback for feedback sake. It’s fine to not have any genuine feedback to contribute.

113

Chapter 7

Learning

Anonymous or Identifiable Our peers will feel more comfortable if their feedback is anonymous and taken into consideration by the manager, but this allows a greater likelihood of “vent feedback,” which is the gripes someone has about their peers under the guise of feedback around their performance. It becomes a judgment on someone else, rather than something specific for them to focus on. If feedback is identifiable, it will almost always be overwhelmingly positive because, as human beings, we much prefer to hold our tongue on anything not positive. I used to approach peer feedback in the same way as engagement surveys – anonymous comments rolled up into a report – but I think that was a misstep and dilutes how effective it can be. I’ve since seen better results by managers identifying a very small number of peers (two or three maximum) who have worked closely with their team member, speaking to them first around the specific areas of feedback that are seeking, allowing those peers to contribute this feedback in an identifiable way to the manager, and the manager taking that into account in their feedback conversation with the team member.

The Filter of Perception I’ve had 360 feedback processes done where one comment will contradict the next. It’s not that either of those comments are invalid or not real for that person, but rather a symptom of how we perceive feedback. We put our own individual filter and biases on the feedback we give and receive. What we want to see more or less of in someone else is not automatically true. It’s just our perception of it, and therefore input to how they might think about that specific area of development. For managers, this means helping people identify and place a filter on the feedback they give and receive. Feedback is helpful to understand ourselves and those around us, but not all feedback is equal and there’s an art to how we process and use feedback to grow. 114

Chapter 7

Learning

T he Perfect Resignation: When the Time Is Simply Right My voluntary turnover target in any startup I work in is never zero. It feels counterintuitive – while we know that involuntary turnover is unavoidable, voluntary turnover is something we theoretically should aim to never happen. If we build a truly sticky people experience, why would we want someone to leave? There is one scenario that gives me warm, fuzzy feelings inside and it relates to resignations. It’s the person in our team who has aspirations to do things that are simply not possible in our startup. It might be a passion to make a difference in an industry that is vastly different from where they’re at (e.g., transitioning out of FinTech into ClimateTech). It might be an increasing entrepreneurial spirit that drives them to go and start their own business. Or even, they’ve grown into a bigger role that doesn’t exist at our startup. These are great reasons to leave a business, and something I believe as leaders in startups we should be supporting and advocating for. You don’t spend an entire career in a single startup, like you can in other industries and in larger companies. The time we have people in our startup will come to an end, so I like to think of the people experience as trying to make it as sticky and fruitful as possible, and for our people to be well positioned at the end of their time at the startup to take whatever next step they are aiming for. Don’t get me wrong, it will always feel bittersweet because I’m a selfish person and someone leaving for however great a reason will still be a loss. But when the time is right for someone to pursue something not possible within a startup, it’s a perfect resignation. In this chapter we’ve covered a number of parts to how we learn and grow that also impact and overlap with how we think about high performance in startups, so in the next chapter we’ll continue that flow into the world of performance.

115

Chapter 7

Learning

Summary 1. Being part of a high-growth startup is a reason to invest in and focus on learning, not an excuse to do the opposite. I typically start with the growth and development culture and nurturing that, nailing onboarding and building a great team of managers to amplify impact across teams. 2. It can be easy to think of learning as a series of online courses, conferences, or reading books. But that’s not where most of the learning actually comes from. Our approach to learning needs to be grounded in experiences for people – tackling new projects, mentorships, learning from mistakes, and stretching responsibilities. 3. Progression doesn’t have to mean promotion, and it will mean something different for everyone. For our work in this space to be effective, we need to understand and tailor our work to how each individual views their own progression and what they’re trying to work toward. 4. Peer feedback is equally as helpful as it is dangerous. We should carefully plan how we build skills in giving meaningful feedback, ensure appropriate and safe forums in which that feedback is provided, and help our people know what to do with feedback too. 5. Not all resignations are bad. There are great reasons to leave a business, and when someone leaves who has aspirations to do things simply not possible in our business, we should be excited for them and grateful for their time with us. 116

CHAPTER 8

Performance In the last chapter we explored how we learn in the context of startups, and some of the mental notes I’ve taken to approach this very broad area. One of the themes through learning is the growth of our people. In a startup environment, growth is critical to how we also think about performance – the mindset and behaviors required by managers to support their team members, the clarity of direction and goals that ensure everyone is pointed in the right direction, and how we think about the cycle of performance and development in the context of a rapidly growing and scaling startup. This chapter continues that chain of development and growth from Learning and shares the lessons and principles that have stuck with me when thinking about high performance and how we create environments where our team members can thrive.

The Trinity: What, How, Where? Typically, when we think about performance and how we help both managers and their team members, we spend an awful amount of time talking about goals and underperformance. Goals can be super powerful and create alignment and buy-in, which is necessary and gets increasingly harder as the business grows and becomes more complex. And underperformance is an unfortunate reality of managing people. Even the best teams have an underperformance quotient that they need to manage.

© Patrick Caldwell 2023 P. Caldwell, People Ops, https://doi.org/10.1007/978-1-4842-9819-0_8

117

Chapter 8

Performance

This emphasis on goals and underperformance, as important as they both may be, both relate to specific steps in performance rather than how we actually go about driving performance. Managers have a tough gig in this regard. A lot of the training they have done in the past introduces an abundance of theories, models, frameworks, and concepts for how to manage performance, and people, well. It’s a monumental amount of information to take in and it’s easy to feel overwhelmed. And let’s not forget what was shared in the previous chapter around how people learn too! I’d guess two or three times a week, I speak with a manager or team member about something performance-related within their team. Something mightn’t be clicking between the manager and team member, or there’s ambiguity around the role or expectations, or something personal going on, or one or either of them have no idea what the point of the work even is. It’s a surprisingly finite list of things that tend to get in the way of the peak performance we’re trying to find. It’s especially hard for managers who are managing a team for the first time. Being able to take all of the things, and all of the advice, for what they know they should be doing and convert it into action that is effective. As I reflected on hundreds of these conversations with managers and team members, I was trying to find a silver bullet for how we prevent this from happening. It doesn’t exist. But there are patterns with the sort of things that regardless of team, experience, and personality continue to pop up. Boiled down to their simplest form, they’ve become a series of three questions. This is a model (I know, another model to add to the mix) I’ve been using for a number of years with managers and team members alike. I frame it as making sure the 101s are in place and constantly revisited and reinforced throughout the interactions that happen between managers and their team members. Secretly, it’s been more about trying to proactively reduce the likelihood of people and performance problems ending up with the People team to help work through. 118

Chapter 8

Performance

The model is this: as a manager, if you do nothing else, make sure you help your people answer these three questions: 1. What am I doing? 2. How am I going? 3. Where am I going? Let’s break it down a bit further. “What am I doing?” is about role clarity and expectations. While some team members might intuitively know what they need to be delivering, for the vast majority we need to revisit this all the time and be explicit about what we’re working on. This means prioritizing what comes first to avoid a misfire of focus, clear expectations for what is delivered and, by when, any barriers or roadblocks that might put this at risk, and generally having an open discussion with each team member to understand their workload and where they are spending their time. Quick reminder: This doesn’t require a thrice-daily Slack message to check in on what someone is doing. You can cover all of this as part of your 1-1 and should carve space out for exactly this. “How am I going?” is a bit of a double-edged question, so it could easily be split into two components. Firstly, it’s a check in for how your team member is going. What’s on their mind, how they’re feeling about their work, and assuming you know them well enough and they’re comfortable with this, how things are going outside of work too. Usually we kick off a 1-1 with a question that touches on this, before accepting the default “pretty good” response and moving straight to the next thing. This question is really about making sure you’re in tune with your team members. The second component is helping your team members understand how they are going in their role or with the work they’re doing. Humans need reinforcement, encouragement, praise, and sometimes correction and alignment. And in a work setting, the feedback provided by managers for any of those purposes is gold dust. Never assume your team member knows how you’re feeling about their performance. And please, never operate the “no feedback is good feedback” management style. Your team deserves better than that. 119

Chapter 8

Performance

“Where am I going?” relates to purpose and direction for both the business and each team member. As startups grow, the mission can feel quickly removed from the day to day and it’s vital to performance and motivation that people see the link between what they’re working on, what others are working on, and overall what the business is trying to achieve. This also aids in building empathy and a team mentality for when things go awry or not to plan (these are called weekdays in startups, so doubly important!). Direction can also be at a very individual level and relates to how we perceive growth and progress from the last chapter. The day-today roller coaster of work can sometimes cause tunnel vision and it can be difficult to see what we might be working toward from a personal level. These three questions don’t only apply to managers but also to team members too, with a slight reframe. When we’re feeling like things aren’t quite clicking the best they could be with our managers, or there’s been some misalignment or conflict, these are three questions that can help bring back the clarity, purpose, and alignment needed to operate more smoothly.

I Messed Up OKRs, Twice! I’m about as far from an OKR expert as you can be, especially for someone in my role. I dove head first into OKRs on two occasions and would kill to have my time again. As is the theme with almost everything in this book though, messing up is rarely a bad thing and it’s given me some much needed perspective on why I should never underestimate OKRs or generally how we go about setting and communicating goals. For the record, this lesson is not about criticizing OKRs, but rather the reality check from implementing them poorly.

120

Chapter 8

Performance

The first time we launched OKRs, our aim was to bring the whole company on board with a bottom-up build of initiatives that would feed our top-level objectives. We hosted workshops, facilitated team discussions, and gave everyone the opportunity to contribute to how we were going to smash it out of the park that quarter. Even with a relatively small team we had hundreds of initiatives contributed. Some of them related to the company objectives and many others fell into the “these would be good to do at some point” bucket. The prioritization of these left a lot to be desired, but we ended up with a set of initiatives and some half-baked key results and metrics. Good enough, we thought, and we set sail into the quarter! What became brutally obvious as we moved through the quarter is that we’d gone through the entire process seemingly blind to the day-to-day of the startup. Almost every single initiative was something new to improve or enable the business. There’s plenty of value in that, but we were going into OKR progress updates and hearing feedback like not having enough time to meaningfully move forward most of the initiatives. We’d placed OKRs on top of everything in the business, rather than integrated into what we were doing, and it ended up only having a slither of the positive impact it was capable of having. The second time around was painfully amusing (in hindsight, it was less amusing at the time!). We overcorrected and then some! We found a better balance of objectives and key results that reflected both incremental growth to our core business and some opportunities and threats that we carved out as focus areas. It wasn’t until one of the final OKR progress updates that we sat around chuckling at the fact our sales team had hit almost all of their key results without completing a single initiative. On one hand, we can’t complain too much as hitting the key results is a great outcome for the business. On the other hand, we still failed to bring value from the methodology and couldn’t be confident of the link we’d created from initiatives to key results to objectives.

121

Chapter 8

Performance

During future goal-setting processes at this startup and others, I’ve probably been a bit adverse to most of the methodologies that exist and it’s only been more recently I’ve come back to believe in the power of the link between the work that we do individually to the measurable outcomes for the business that contribute to our objectives. Something that I reflect on often with my brief foray into OKRs is the need to contextualize according to the stage of the business. We do this in almost every other part of the people landscape, from how we approach recruitment and onboarding to how we do compensation and benefits. I skipped this step with OKRs and tried to achieve a methodology rather than using and adjusting a methodology to achieve the business goal. The value of OKRs wasn’t void during this process. It was messy and ineffective in a lot of places, and we probably wasted too much time working out whether we were aiming for three or four of a certain outcome as part of defining key results. But what it did do is put front and center a cadence to come back and communicate more about our objectives and what we were trying to achieve. Every month we were talking about the same thing, and then during the month it came up again and again in team meetings. Our team became fluent in our direction and ambition, even if we muddled everything below this. And that’s a pretty good outcome as a starting point to build on again.

 eople Outgrow Startups; Startups P Outgrow People During an interview process for a new role, the Founder and CEO and I were discussing some of the pains of growing the size of the team by a large multiple year on year. Toward the end of this, he asked me, “What’s one piece of advice you wish you were given before your last growth journey?.” And I said this: “People will outgrow you, and you will outgrow people. Both of those things are fine.” 122

Chapter 8

Performance

In the previous chapter, I shared the concept of people and startups outgrowing each other as part of the focus on growth culture. It crosses over both performance and learning, and it’s arguably a lesson from my time in all startups that never stops resonating. Or being true. Startups are incredibly fluid businesses. They experience significant amounts of change in a short space of time, which is why there’s an adage within startups that a year in a startup is worth two anywhere else. We’ve become accustomed to hyper-growth stories, where a small team with early traction and some investment quickly balloons to having a huge valuation, several hundred or even thousands of people, and sometimes still expanding. These startups needed to continuously reinvent itself, and it’s likely that every couple of years the business would have felt unrecognizable by some. I covered the perfect resignation at the end of the previous chapter which is the best reason why someone might outgrow a startup. But it’s probably not the most common, which is the scenario where a team member is seeking a step up to a role that doesn’t exist at that startup, either because it’s occupied or because it doesn’t exist yet, and they go and pursue that elsewhere. The growth curve of many team members can be just as steep as the growth curve of the startup, and I’ve come to accept the reality that there’s always going to be a subset of this scenario that you can’t plan for or fix, and that the best thing for that team member as a person might well be in another business. The second part to this lesson is the reverse, which is an unfortunate reality of growing quickly especially in senior roles. Let’s take a B2B education technology startup which is experiencing significant revenue, customer, and team growth. Within their first few years, they might have grown their revenue from $1 million to $10 million, and in the few years after that, from $10 million to $50 million. Their customer numbers have gone from tens to thousands, and their 15-person team as part of an early stage of funding is now several hundred. While this all will happen within one startup, for those part of that journey it will have felt like they experienced several startups. The journey to the first $1 million in revenue 123

Chapter 8

Performance

is scrappy and all about initial traction, feedback, and market fit. To $10 million, it shifts to go-to-market, technology development, and stability, and reaching that period where scaling a business is possible. And to $50 million, it becomes about the ability to grow in a repeatable and scalable way. Each of these environments looks vastly different, and while some people can thrive across different stages of growth, most people generally have a stage of growth that is their jam. Imagine you’re hiring your first sales leadership role. You have a couple of million in revenue and some sales reps in place. You’re now looking for a sales leader to take the early stages of the playbook and likely take over sales leadership from a Founder. They might be expected to be a player-coach, securing revenue through new deals but also building foundations for a revenue engine capable of doubling or tripling revenue. If you were hiring for this role, you’re unlikely to want to hire the sales leader who has spent their career in $100 million revenue organizations with all of the infrastructure in place already. You’ll be looking for someone you have confidence in to deliver what you need in your startup at your stage of growth. And if all things go well in the coming years, that sales leadership roles start to look very different. Almost unrecognizable from the role you needed not long ago. It’s possible your sales leader can grow with the role, or might have had experience across multiple stages of growth and can bring transferable learnings, but if they’re like many leaders in the startup space who have built their success on that stage of growth only, you may well outgrow them and need to bring in a different sales leadership role. This same scenario can apply to almost every part of a startup. My jam is pretty early in startups, typically as the first People or HR hire. If a scale-up already has 1,000 people across 20 countries and with a 30-person People team, they’re likely to need a leader who brings their experience and learning from that stage of growth. Equally, that leader would have likely found the experience of being the first People hire to be quite the shock if they haven’t done it before… Just like I did. 124

Chapter 8

Performance

I’m a big believer and advocate of finding paths for as many people as possible to grow with our startup, but not blind to the fact that with a business that experiences such significant change and transformation in a short space of time, it’s OK to outgrow someone. Just like it’s OK for someone to outgrow us. P.S. One day, I will tackle the 1,000-person scale-up!

If I Hear “Hire Slow, Fire Fast” One More Time… It’s the business adage gift that just keeps on giving. Take your time hiring and be highly selective and sure of the people you bring in. And if they’re not working out, remove them quickly. I won’t argue with what you might think are the opposite practices to this. Any startup that hires whoever they can find in order to grow quickly and then allows for continued underperformance or a strong values misfit is probably going to hit choppy waters really fast and require a lot of reparation. But let’s not kid ourselves into thinking that “hire slow, fire fast” is the goalposts for startups, or any business for that matter. For years, we’ve built recruitment processes made up of six, eight, or even ten stages to put candidates through every possible test, most of which are pointless, to try and perfect the science of hiring perfectly. Most major tech brands are all renowned for convoluted assessments and needing to spend significant amounts of unpaid time and expertise trying to give them an extra 0.1% confidence in the hire. They can do this because their brand and offering is so attractive to so many people that candidates will try and fight through the process, in hope that greener pastures are on the other side.

125

Chapter 8

Performance

I’ve experienced a recruitment process that dragged on for months and had six stages before I withdrew. My engagement with the process went something like this: –– Stage 1: Consider me interested. –– Stage 2: I like this a lot. Very interested! –– Stage 3: Hire me please! –– Stage 4: OK, fine, but get to the point. –– Stage 5: Sigh, really? –– Stage 6: I’m not interested. Now I may not have been that 10/10 hire for them, but I have to trust that at Stage 6, there must be enough interest at their end to want to keep investing their time, and to keep trying to test one more thing. By the end of this process, it didn’t matter how strong of a fit I was because I had lost my interest and engagement in the process. I suggest a change to the first part of this adage. Don’t hire slow. Hire with purpose. Design a process to test the critical requirements and components of the role that allows for decision-makers to arrive at a conclusion in the quickest amount of time. If you’re taking over a month to hire someone, with the exception of processes that involve a lot of travel or logistical challenges, it means you’re not sure what you’re looking for or how to know you’ve found it. Invest time early in the process, before candidates are engaged, to make sure your hiring process is purposeful, but not slow. Fire fast. There are circumstances where this is simply bang on. Where behaviors and values in particular are compromised, the effect of allowing this to continue is infectious and toxic. Similarly, if someone new is not working out, or where a performance issue continues to not improve after you’ve made genuine attempts to try and solve this, taking action quickly makes a lot of sense. 126

Chapter 8

Performance

However, once again I can’t help but notice that the preceding examples are usually not the scenarios where fire fast is used as a tactic. The countless examples of people unexpectedly losing their job after providing feedback on something or someone in the business, the performance issues that go unmanaged for months and sometimes years before a quick process is run to exit someone, and let’s not forget the layoffs that plague the tech industry and the obsession when an indicator turns red to reduce the team size (the same people put through months of recruitment stages to make sure they’re just right for that culture and role). That’s how fire fast plays out in too many startups and it does the ecosystem and People teams no favors by this behavior continuing to exist. So it feels appropriate for a change to the second half of this adage. Don’t just fire fast. Fire thoughtfully. Fire as though it was you receiving the news, or a member of your family. Exhaust every reasonable avenue to resolve situations before needing to make the call to part ways. And if that doesn’t work, fire respectfully and with sensitivity. These decisions affect people for years and can easily come back to bite your brand for both employees and customers.

The Death of Performance Reviews? My first experience of a performance review was in a 50,000-person company. It was exactly as you expected. An annual review, a performance rating from 1–5, and a salary and bonus outcome determined by this. I always thought it seemed a really sensible approach to linking in performance and reward, and I still do. The piece I was missing though which I didn’t realize at the time is how fortunate I was to have a series of managers who were all very strong at what they did, and it was their leadership behaviors that enabled that system to work.

127

Chapter 8

Performance

The longer I spent in HR and People teams, the more it felt like my experience of performance reviews was an anomaly. I would hear of people who felt like they had nailed it in their roles to be told they are “meeting expectations.” Or they were told by their managers that they would rate them higher but they’re only allowed a certain number of people above a line. Or a whole year’s worth of feedback was collated and dumped in one go on the team member, and told where to improve for next year. It shouldn’t be surprising that we look at the system and think “it needs to go.” As more and more businesses started sharing their plans to remove the annual performance review and move to continuous feedback or other cycles, I felt like I had to get in on it. Every major consultancy in the world was publishing reports on the death of performance reviews, so surely there had to be some merit behind this, right? Fast forward to today and I’ve had the opportunity to design and implement a few different types of performance cycles, and also spend time with a lot of other people doing the same in their businesses. I found great amusement in two scenarios that I kept hearing. Neither of them are bad scenarios. Just amusing ones. 1. We’ve replaced annual performance reviews with quarterly performance check-ins, and we’ve decoupled performance and reward outcomes. Salaries are now set based on the market with high performers being incentivized through other compensation means. It’s a shiny way of saying we’re designing for more frequent feedback and still linking performance and reward but in a less clear way. 2. We’ve removed performance ratings and instead use a framework or matrix to calibrate reward outcomes to make sure they’re consistent. This is also known as using a form of performance rating, but without the team members knowing. 128

Chapter 8

Performance

I am being flippant with these scenarios to highlight a couple of things that can be lost in performance cycle decisions. Firstly, we need to view our performance cycles from a team member’s perspective first. At its core I believe we’re all looking for similar things within a performance system – recognition for the work we do, feedback on how we’re going and how we can grow, a feeling that we and our team mates are being treated fairly, and confidence that we’ll be financially rewarded for performing well. If we know these to be true for most people, it stands to reason that almost every performance system could work. This leads to a second point, and perhaps the summary of what I have had to learn. The culture and leadership behaviors of a business determine the effectiveness of a performance system. It’s not the system itself that fails a business, but rather how well it’s implemented and supported. Given every startup will have a different culture, I don’t believe in a single, correct performance system that will be effective by design. Instead, I wanted to share a number of areas to consider to help enable whatever performance system you decide on.

Forced Distribution Possibly the most famous gripe of an annual performance rating. Also known as a bell curve, this is where it is assumed every team will, and therefore must have, a distribution of performance ratings. The origin of this isn’t grounded in some theory of human behavior, as common as it may be to see some sort of distribution. It’s instead grounded in budget. Where a link between performance and reward exists, there is a budget line item to cover salary increases, bonuses, and any other form of compensation. This is typically done on a “middle of the curve” basis, so if you budget a 3% salary increase across the board, your middle performance rating will receive something around that level, and in order to fund your high performers receiving more than that, you need an equivalent set of low performers to receive less than 3% and balance it out. 129

Chapter 8

Performance

Budgeting for performance-based reward is always tricky, especially in high-growth companies where typically your ability to fund reward outcomes comes from meeting revenue expectations which can be steep targets. A different way to think about this is to budget higher than “middle of the curve.” The idea you’re budgeting for a 2–3% increase to cover cost of living and expecting high performance from your team members makes no sense. If you’re striving to embed a high-performing culture and tackle steep ambitions, you should be budgeting for the high performance your team will need to display to reach that. If the results validate this at the end of the year, you have budget to financially recognize your team. If you’re using ratings, the biggest concern your people will have is forced distribution, so you need to make sure this doesn’t sneak into the process and provide enough clarity and transparency on the link between ratings and reward to allay concerns that they’ll be rated based on how they stack up to the rest of the team rather than on their own individual performance merits.

Review Bias This is largely a manager capability and one of the most important roles a People team can play. There are so many natural, human biases that impact our perception of our own and other people’s performance. Being aware of things like recency, attribution, and halo/horns in advance, setting clear expectations and calibration between managers in advance of feedback and review conversations, and having a feedback loop on the process itself from both managers and team members can all help to identify and mitigate the impact of biases playing out.

Deferred Feedback Ah yes, the old “hold that until their review” which might be in four weeks or eight months depending on how deferred the feedback really is. One of the best parts of the rethinking of performance reviews across companies 130

Chapter 8

Performance

has been the recognition of deferred feedback. The value of feedback that is held until a performance review is a fraction of what is can be if delivered in a timely and continuous way. The test I use with managers where a periodic performance review process happens is this – there should not be anything new raised in this conversation. The performance review is a reflection, not an opportunity to bring up new feedback. That should have taken place already, and if not, it’s a reflection on the manager’s performance, not the team member.

Rating Emphasis There’s some nuance to ratings and a few challenges with how they’re implemented. One of the main ones I have stumbled on a few times is where the rating itself, especially the title of a rating, gets in the way of a meaningful conversation. This is a risk of the direct link between performance and reward and often why I try to keep the rating as part of a reward conversation rather than as part of a performance conversation. As humans, we see the number 3 on a 5-point scale as meaning average, even if you intend it otherwise. Similarly, “meeting expectations” can feel really underwhelming if the feedback you receive is that you’ve gone over and above. Performance ratings aren’t for every business, so it’s a judgment call on what will be effective within your culture. If you do use them, engage your team members early in the design of these and listen to their feedback and suggestions on how they are applied. This chapter was the last of four chapters dedicated to key functional and lifecycle areas within our People experience: Recruitment, Reward, Learning, and Performance. In the next chapter, I wanted to call out something very specific which has become much more topical and relevant since 2020. You guessed it, remote working.

131

Chapter 8

Performance

Summary 1. Managing a team can feel overwhelming trying to get everything right and avoid all of the pitfalls you’ve been warned about. It can be helpful to strip it back to fundamentals. If you do nothing else for the moment, make sure you help each person in your team answer these three questions: What am I doing? How am I going? Where am I going? 2. If you’re building a goal-setting process for the first time, don’t be afraid to experiment and don’t be disheartened if you get it wrong. I messed it up a few times, and with each iteration and improvement, it gets closer to a great goal-setting process. 3. There are two truths about people and startups. Number one: people outgrow startups. Number two: startups outgrow people. Both are perfectly OK when we can’t find a path for someone. 4. Swap out your “hire slow, fire fast” mentality for one that is people-first. Hire with purpose. Design a process to test the critical requirements and components of the role that allows for decisionmakers to arrive at a conclusion in the quickest amount of time. Fire thoughtfully, as though it was you or a member of your family receiving the news.

132

Chapter 8

Performance

5. It can be difficult to know what best practice performance reviews look like, but in my experience it’s the culture of the business and the manager’s behaviors that have the most impact on success rather than the specific design of the performance cycle. Avoid forced distribution and deferred feedback, identify and mitigate reviewer bias, and be mindful of how you define ratings if you choose to use them.

133

CHAPTER 9

Remote Working While there are fascinating links between remote working and the components of our People experience that we’ve covered in the last four chapters, it feels necessary to call out this topic specifically given its relevance since the Covid-19 pandemic. This chapter shares some pointed observations about how we’ve coped with and continue to manage remote working, as well as how we start to think about flexibility and the rise of the remote manager.

The Covid-19 Acceleration Remote working existed long before the Covid-19 pandemic. Some truly incredible businesses built remote teams and cultures that have been enviable examples for others. And in the space of a few weeks, the vast majority of white-collar work was forced into our homes, bedrooms, living rooms, and families as restrictions set in across the globe. For these people and businesses, remote work was now the status quo. Remote work is not any better or worse overall than non-remote work. For some people and startups, it works well. For others, it doesn’t. And that’s perfectly OK. There can be more than one correct answer and the constant battle between remote work advocates and critics alike is pretty pointless.

© Patrick Caldwell 2023 P. Caldwell, People Ops, https://doi.org/10.1007/978-1-4842-9819-0_9

135

Chapter 9

Remote Working

The pandemic represented a fascinating change curve for a lot of businesses. There wasn’t time for planning. Most businesses probably treated it as a continuity crisis. In addition to widespread illness, wellbeing concerns, trauma, and loss, remote work was forced into many workplaces and we needed to make lemonade. And so that is what happened. Businesses with decades of in-office history made swift and impactful changes to allow for continuity. It didn’t matter if you were a remote work advocate or not, you simply had to make do. Very few good things can ever come out of an event like a pandemic. But we witnessed a symptom of the pandemic which was the adoption and practices of remote work. We experienced possibly decades of progress with remote work adoption in the space of twelve months, and so now as we come out of the pandemic, we shouldn’t be surprised to remain in a teething period for quite some time. The change was a shock to the system, and now that a choice has returned for a lot of businesses, we’re starting to cast a more critical eye on the sort of arrangement and culture we’re trying to build.

 emote Work Is Uncovering Our R Dirty Laundry “How will I know they’re working and not slacking off?” “You can’t be as productive from home as you can be in an office. There are too many distractions at home.” “We value flexibility and you’re allowed to work remotely one day per week.” My word we are airing some dirty laundry, aren’t we? Whether you’re a fan of remote working or not, I’d like to think the acceleration of progress in remote working, especially how to do remote working well, is a great thing. It’s opened up a much broader understanding of how we behave 136

Chapter 9

Remote Working

and think as humans, and how we operate as part of a team and business. It’s also brought out our dirty laundry. They aren’t secrets in the world of work, but rather have been amplified through the transition to remote working and have taken center stage as businesses consider the work arrangements of their teams.

Performance There is no better way to say you don’t know how to measure the performance of your team than to be genuinely concerned they are slacking off when they’re at home. Because if you did know how to measure a team member’s performance, you wouldn’t be concerned. At worst, you’d be really curious. It might take a moment of self-reflection for each manager, myself included because I too have been guilty of this, to question if the physical presence of someone working near you in an office has been mistaken for performance, even on a very small scale. When we identify and remove that mistake, it allows us to start over with how we think about performance for each team member. Working together to define outcomes and goals rather than just inputs and effort. And once those are defined, let’s be curious about how or if remote working influences that.

Trust Trust is central to the relationship between managers and their team members, and remote working has added some chaos to that trust. There is a logical follow-on from the example earlier about worrying that a team member is slacking off. A big part of that is performance, and another part is likely trust. Highly trusting relationships would already have the empathy and authenticity behind it to work through that belief system and arrive at a positive outcome.

137

Chapter 9

Remote Working

Trust played out in the world of remote working in a whole variety of ways. Take those people who joined remote companies during or just after the pandemic. They joined under an agreement that they would be in a remote role, and once offices started reopening, many were met with requirements to relocate to be in an office for a period of time, or risk losing their jobs. The same thing applies to the sheer volume of layoffs that took place in the last few years, sometimes leaving people without key benefits or any level of financial stability until their next role. If we want to talk about how to erode trust in the shortest number of steps, there is basically a playbook on our door from the last couple of years. Trust is complex and dynamic and takes a long time to build and nurture. Remote working has aired the poor state of trust between many managers and their team members, and between team members, and is now contributing to some of the blanket decisions being made to enforce working arrangements in a certain way. It should come as no surprise that so many of the fully remote businesses who operated that way since well before the pandemic cite building trust and relationships as so core to their values and ways of working.

Culture There’s been a meme floating around since offices started reopening at the back end of the pandemic. It shows a lifeless office of cubicles with words to the effect of “we’re returning to the office because we care about our culture.” If you remember back to Chapter 3, you’ll already know my opinion about culture relating to something so insignificant like an office. But this meme didn’t become so popular just because it was funny. For so many people, this was real. Their business had chosen to return to the office under the banner of trying to nurture their culture, without any real shared understanding of what that even means. There may well be some very valid parts to how they’re thinking about their culture in

138

Chapter 9

Remote Working

a deliberate way, but without this context or any detail around what specifically they are trying to achieve, it will continue to be perceived in its most negative light (and rightly so). Culture happens whether we like it or not. And as we already discussed in Chapter 3, the question is around how deliberate and purposeful we want to be with the culture we’re building. There are great cultures within remote companies and great cultures within non-remote companies, just like there are poor cultures within both too. We should start with the culture we’re trying to build to understand the role of remote, hybrid, and in-person arrangements in helping to shape and reinforce that culture.

 now the Difference Between Flexible K and Remote Work At risk of sounding a wee bit condescending, I thought it might be helpful to recount the definitions of a few terms we continue to use more interchangeably than we should.

Remote. Hybrid. Flexible. It can be easy to blur the lines between these when describing the sort of arrangements that take place or might be possible. Similarly, we might describe how we prefer to work individually in a different way to others or different to how businesses describe their setup.

Remote This describes working outside of a company’s office or place of business. It doesn’t have to mean working from home. It might mean working from a bookstore or working from my parents’ house in Australia. Sometimes, businesses will define it one layer further with additional terms below which I’ll share the going understanding of: 139

Chapter 9

Remote Working

–– Fully remote: Everyone works remotely all the time. Some companies will give complete choice around where their team chooses to work also. –– Remote-first: Everyone is assumed to be working remotely but there could still be options to work from an office location. Typically, these businesses will structure their operations around a remote team. –– Remote-friendly: Everyone is allowed to work remotely at least some of the time, but they aren’t assumed to be doing so. This is sometimes known as a combination of hybrid and remote, as some people will use an office and some people may be fully remote.

Hybrid Hybrid assumes that everyone needs to be in a company’s office or place of business at least part of the time. Businesses that require a day per week, or a week per month, for instance, would be described as hybrid. Hybrid assumes there will be times when everyone is together and when everyone is apart.

Flexible Flexible work cuts across remote, hybrid, and in-person work arrangements, but it can be difficult to separate out the language given how readily remote and hybrid work are described as flexible work. Flexibility is where work can be adjusted by a team member based on their needs. It might be where work is done, or how it’s done, or when it’s done. Flexibility can exist in all forms of remote, hybrid, and in-person arrangements and can also be missing from all of them too. A company that mandates every team member must work from home and with set 140

Chapter 9

Remote Working

hours and breaks is not somewhere a lot of people would describe as being flexible, even if it’s remote. Similarly, it can be tempting to describe hybrid arrangements that require two days a week in an office as being inflexible. For some, they might consider that. But if you have the ability to set those two days, to increase or decrease it as other things arise, and to also adjust hours and breaks to what works for you, you might find there are a lot of options for flexibility. The reason why defining these individually is important is to uncouple flexibility from the concept of remote, hybrid, and in-person working. By simply choosing an arrangement, we’re not automatically flexible or inflexible, and we still need to be in sync with the sort of flexibility that our team members might be looking for in order for a work arrangement to work for them.

The Remote Manager I’ve worked in a number of different remote businesses and been fortunate enough to work with some exceptional managers who have taught me a lot about how remoteness can influence how we engage, motivate, and interact with our teams. I genuinely feel for all of the managers who became overnight remote managers during the pandemic. As humans, we all had things to deal with in our lives, and managers had an extra pressure on their ability to transition to remote management and wear that hat well for their team. There are a lot of tweaks to management style and behaviors that remoteness requires, but overwhelmingly I’ve found there are consistently three areas of remote management where the exceptional managers stand tall. They nail these three things, and as remote working continues to become more prevalent and understood in the coming years, I fully expect these will start to appear more explicitly on.

141

Chapter 9

Remote Working

Synchronous and Asynchronous Communication There’s a fine art to communicating with remote team members and knowing what sort of communication will achieve the best outcome for each team member. Unsurprisingly, things like 1-1s and social activities are almost always synchronous and fundamentally designed to bring people together. Likewise, purposeful synchronous forums to allow for discussion and debate, coupled with asynchronous forums where time zones impact participation, make sure that each person still feels included regardless of where they are at. And, something that is consistently underrated, a culture of writing and documentation to record discussions and decisions, clarify processes and steps, and help support the selfservice of new team members.

Onboarding Speaking of new team members, onboarding remotely has a different flavor to rocking up to an office for your first day. But for these exceptional managers, onboarding never started on day one. It started way back in the recruitment process with the expectations and transparency they demonstrated around how their teams worked and even some of the challenges. And once someone had accepted an offer, preboarding processes were in place to start to prepare someone for stepping into the team, especially making sure they knew what their onboarding would look like, what equipment and support they’d have, and how they’d meet and work with their new teammates.

In Tune with Work and Well-being I remember being in an interview for a developer who would be joining a fully remote team. When we were talking about remoteness and how they liked to work within remote teams, they made a comment around how 142

Chapter 9

Remote Working

they appreciated managers who knew and trusted what they were doing but didn’t feel the need to check in on Slack ten times a day to make sure of it. It stuck with me, for both the honesty and for a nuance in remote management that exceptional managers just seem to nail. Being in tune with each team member’s work and their well-being. There’s a balance to staying in tune without coming across overbearing, especially when you lose some of the body language from inperson conversations. Exceptional managers carve our time to deliberately and purposefully discuss work and work outcomes (and trusting it gets done when they say it’ll be done) and also on how people are going as humans. Meaningful check-ins to learn about them as individuals and explore how they’re thinking and feeling about things.

Burnout Is Our New Thanos It’s a logical flow from the previous lesson around being in tune with each team member’s well-being, and especially important given some truly sobering statistics that are coming to light around how burnout, stress, and pressure play out on remote team members. Over 35% of men and 42% of women feeling consistently burnt out at work was reported by McKinsey. Some other publications reveal this rate to be much higher too. Zippia found that two-thirds of remote workers feel pressured to be available all the time. And it’s been shown consistently in research for years that those who experience burnout are more likely to be absent. Gallup’s research puts this into perspective – team members who feel burnt out are 63% more likely to call in sick, and 2.6 times more likely to be looking for a new job. Now, before we assume that remote work is the cause, the statistics for hybrid and in-office teams are not that much better. It turns out, burnout is increasingly a risk for everyone. But remote work puts a unique strain on team members through the blur between their work and their 143

Chapter 9

Remote Working

nonwork lives. A lot of us will have seen how easily it can play out during the pandemic, including me. Your desk and your bed may only be feet apart, and with most of our tools available on our phone too, it seems inconsequential at 7 a.m. with breakfast or at 8 p.m. when watching television with the family to fire away a few emails or send a Slack or Teams message back to the boss. This risk exists for non-remote workers too, but there’s a more clearly defined work day which helps some people transition from work to the rest of their life. That delineation is less clear for remote team members who need to mentally check in and check out of work to force it, even when their systems and tools are always close to hand. The next chapter is the last chapter, but we take a sharp right turn to talk about something much more individual than our collective People experience: your career.

Summary 1. The Covid-19 pandemic accelerated decades of progress with remote work adoption in the space of 12 months. Now that we’ve come out of the pandemic and greater choice exists, we should expect to be in a teething period for quite some time as we learn more about how various arrangements can contribute to our teams and culture. 2. Remote work has broadened our understanding of how we think about human behavior and performance in different contexts. It also aired our dirty laundry, in particular whether we actually know how to measure performance, how we perceive and build trust in relationships, and the (lack of) depth in our understanding of culture and what drives it.

144

Chapter 9

Remote Working

3. Be precise in how you describe work arrangements. Remote work and flexible work are two different things, and we should uncouple our thinking on these as being related. 4. A new role has been introduced through the pandemic in many companies – the remote manager. There are three areas, in my experience, where remote managers consistently excel – blending synchronous and asynchronous communication, onboarding, and staying in tune with both work and well-being. 5. While burnout is prevalent and increasing across all work arrangements, remote work has added a new lens to how we identify and respond to unique risks of burnout that it poses, in particular around the blurring between our work and nonwork lives.

145

CHAPTER 10

Your Career This chapter has a bit of a different feel to it. I want to talk about myself. And you. And every member of a HR or People team too. Every lesson in this chapter is something I have struggled with throughout my career. Some of them I still do and need to remind myself constantly to maintain perspective. There is a People team flavor to most of what I share in this chapter, but many of the things I struggle with I know others do too, in different parts of the business and in different stages of their career. So I like to think there’s something here for everyone.

 now the Difference Between Who You Are K and What You Do I’ve worked with mentors and coaches at various points throughout my career and a topic that has come up a number of times relates to my identity, both personally and professionally. Not only how I see myself, but also how I think others see me, and how I want them to see me. Throughout these conversations, there’s a question that really stuck with me and it fits firmly into the bucket I described of things I need to remind myself constantly.

If you lose your job, who are you?

© Patrick Caldwell 2023 P. Caldwell, People Ops, https://doi.org/10.1007/978-1-4842-9819-0_10

147

Chapter 10

Your Career

It’s not intended to be a deep philosophical question even though it sounds a bit that way. It’s simply a guide for reflection. The very delicate balance that I’m sure many of us all live each day is that of who we are and what we do. It can be hard to differentiate these sometimes. When I’m in my zone and passionate about what I’m doing, sometimes my entire view of myself becomes my job title. And it’s easy enough to do. We spend our working hours, days, and weeks playing a part in companies, and regardless of what part we play, it feels very human that we start to see ourselves as that part. We introduce ourselves to new people and go straight to what we do for work. So if that work no longer exists, by your choice or someone else’s, who are you? What gives you passion? How would you introduce yourself to someone you met at an event? Are you a parent? A cyclist? Do you volunteer at a local shelter? Are you part of a community or sports group? These are the things that can and should fill our identity buckets. So if we lose one of them, we’re only pouring out a splash and replacing it. Not the whole bucket. Having breadth in my identity has been a focus for a number of years now. Having been through a redundancy process and feeling it necessary to quit a different job immediately, I’m slowly getting comfortable with the fact that as much as I might enjoy my work on the whole, it is always less permanent than I give it credit for. Change is inevitable, so if I do need to part ways with my job for whatever reason, there are enough other parts to my identity and passion that mean I can wake up the next morning still feeling a sense of energy, purpose, and direction.

148

Chapter 10

Your Career

 e Clear on What Your Role Is and What B It Isn’t Depending on your experience and exposure, the role of a HR or People professional can have a very different meaning to the person sitting next to you. And different again from the next person. There are operational support roles, “back office,” business partners, strategic advisory roles, “people people” roles, and of course the “HR but you’re mostly a recruiter” roles. When you’re the first People hire in a startup, there’s a bit more freedom to define how the role and function shapes up. There are also existing expectations about the role too, so, just like the myth of a blank canvas we covered in Chapter 1, you’re unlikely to be building from scratch. In the first startup I joined, the CEO described a cathartic response from people. I became a sponge for all of the good and bad, which is fine at first to get under the skin of how things happen. But once you multiply your team size that needs adjusting, and the intent of my role was to build a people function, not just be a therapist. The principle that came out of this was defining the people function as not existing to solve problems, but to help others solve their own problems and prevent the number of problems in the first place. How that played out was in approaching conversations using coaching techniques, allowing others to experiment, fail, and learn, and making sure our People team processes were constantly looking at how to arm team members and managers to be informed, empowered, and accountable. Hiring managers were accountable for the hiring in the teams, supported by our Talent Acquisition team as a “guide by the side.” Similarly, people leaders were coached to identify, analyze, and come up with options to solve the people problems in their teams and trusted to do so without the People team needing to be involved in absolutely everything that was happening. This is just one example of setting the tone for what the People team are in a startup to deliver and identifying the value of the People team

149

Chapter 10

Your Career

in that capacity. However, this lesson for me is broader than that. It’s a reminder that if you’re not 100% clear on what you’re there to deliver (and what you’re not), people will fill that ambiguity with assumptions and guesses based on their own experience. And unfortunately, those experiences in the People and HR space can be wildly varied and are not often positive. In the absence of clarity, people make their own.

“I Don’t Know” It’s human to feel a bit shitty when someone asks you a question and you haven’t a clue what the answer is. It’s also human to want to avoid the thought that others around us think we don’t know what we’re doing or we’re underqualified. Yet it’s these two things together that we’d do well to embrace, even when it doesn’t come naturally. To date, I always feel inadequate when someone asks me what we should do in a people or culture situation and I don’t know the answer. It took the wisdom of a fair few founders, investors, and trusted mentors to remind me of two things: 1. In a startup environment, most people are working it out as they go. We might add a pinch of good judgment, some lessons from our experience, and a sprinkle of good intentions. Then we hope for the best. Every startup environment is different and playbooks tend to be few and far between for how to navigate so many different situations. Even this book is really only scratching the surface of the people space in startups.

150

Chapter 10

Your Career

2. No one knew what they were doing the first time they did it. It’s a universal truth about starting something new, be it in any industry or profession around the world. And the fact we are doing something new is already a massive learning milestone and how we can grow our skills. These two things are part of the fun and journey of building and scaling startups. It’s usually our own pride that gets in the way of having a conversation where we’re vulnerable enough to admit we don’t know the answer. So instead we fill that space with empty words that are, at best, waffling around without answering and, at worst, a poor attempt at an answer that may be wrong and dangerous to the startup. I’m guilty of both, yet even in the moments where I chose to cover up my insecurity, I realized it did no one any good. I didn’t feel any better in my ability to waffle out an ambiguous and unhelpful answer. And I certainly never felt better guessing the answer on my own and allowing others to believe I knew what I was talking about. I needed to stop pretending and start accepting those two points earlier. What has been fascinating to experience as I started to make the transition to saying “I don’t know” more often is the effect it had on those around me. It wasn’t met with condescension, at least to my face! Instead, it became a chance to work together and collaborate. A problem that needed ideas, debate, advice from others, and a chance to figure it out together.

Find Your Outlet A bit of self-love goes a long way, especially in People teams, or in any role with responsibility for people and culture. You will be part of difficult conversations that make you feel sick, upset, or guilty. You will see the best and the worst of people. People will be angry at you because of your 151

Chapter 10

Your Career

role and not because of who you are. You’ll doubt yourself over and over. You’ll be expected to carry an emotional load of stuff that very few people in the company can see, and if you’re alone or in a small team, the support network can be sparse. All of this has a profound impact on our mental health. The very fact it impacts us simply makes us what we are: human. You deal with enough of other people’s “stuff,” so it’s vital you have an outlet for your own, for both your physical and mental health. During the Covid-19 pandemic, my calendar became full of people wanting advice, support, and often just a set of ears. Parents who were struggling with school and childcare closures. People feeling lonely and frightened being unable to leave the house outside of specific reasons and unable to hook in with their network and friendships. Folks who were experiencing significant loss and trauma with elderly and unwell family members and almost no ability to say goodbye. And, generally, everyone who was struggling to juggle so much happening in the world with what their work had become. For months, I was a therapist, friend, coach, counselor, advisor, listener, and many more hats. And then I would get to the end of the day, if not sooner, and sit in my shoebox studio in New York alone and go through some of the exact same stuff myself. I put on too many pounds to count and was forced to pause almost all of the hobbies and activities that brought me joy. This isn’t fishing for sympathy. I came through the pandemic as one of the very lucky ones without significant loss or change, so I’m very fortunate in that regard. But there’s a parallel into mental health in the workplace that feels too important, in hindsight, to ignore. I was trying to be an outlet for everyone else, but forgetting to look after myself too. Once some fitness activities were allowed again in New York, I started to find joy and peace in walking. Sometimes it would be five or six short walks a day as I needed the change of scenery from my coffee-tableturned-desk in my studio. When I left a conversation feeling drained or

152

Chapter 10

Your Career

worse for wear, I walked. If I felt emotions around the pandemic that were difficult to contain, I walked. Even when I just felt bored or restless, I walked. It always found a way to bring me back into a good place mentally. It doesn’t really matter what the outlet is, just that it works for you and meets you at that moment where you are. Could be something physical, something quiet and meditative, something social or something entirely different. It’s where you go to give yourself some love when you need it most.

Be Ruthless with Your Time 10:58 a.m. You’re at the end of a call with three of your colleagues about an upcoming project. James says he’d like to use the last couple of minutes to discuss something which turns out to be entirely new and definitely not a two-minute conversation. You begrudgingly go along with it knowing your 11:00 a.m. one-to-one with Kylie is afterward. 11:03 a.m. You manage to escape James who has booked a follow-up meeting later in the week and you quickly jump up from your chair and pace to the bathroom for a pit stop before hightailing it back to your chair to dial in to your one-to-one with Kylie. 11:06 a.m. “Sorry about that Kylie, I’m back to back today and we ran out of time in that last meeting. You know how it is. I do have a hard stop at 11:30 as I’m speaking to Jesse so let’s dive straight in.” 11:32 a.m. You let Kylie know you’re unfortunately a few minutes late to your next meeting already so need to wrap up and you’ll give her a call tomorrow to go through that last item you were discussing. 11:34 a.m. Damn. You open your calendar and see that your only spare 30 minutes at 12:30 p.m. after meeting with Jesse is now taken by your manager wanting a “quick chat.” Lunch breaks are a thing of the past these days and every day just seems so busy.

153

Chapter 10

Your Career

It’s easy enough to do. Our to-do lists are bursting at the seams; we’re trying to keep up with what is happening and help others do the same thing. What starts as a few meetings throughout the day quickly expands to fill every minute, with our calendar now looking like a completed tetris diagram. You feel you’re permanently late to every meeting and always relieved when Gary tells you he has a clash and needs to cancel just so you have a gap to work on something that was due yesterday. Our calendars have become our actual job, starting each morning not by identifying what you want to achieve that day, but by scrolling through each calendar invite for who you’ll be speaking to that day. A huge disclaimer coming on being ruthless with your time. Typically, the more senior you are in the company, the more autonomy you have over your time. So I wanted to compile tips that would cover the breadth of roles and seniority that exist in every company, despite being very aware that a few of these may be harder to implement for some than others.

Reduce Default Meetings to 20 and 45 Minutes If you’re booking in a meeting with others, calendars default to time blocks of 30 and 60 minutes. So even if your conversation might be done in 15 minutes, or 40 minutes, you’re typically using those blocks to set your time aside. We are great at filling the time available in meetings whether it’s adding value or not. Parkinson would be proud. By changing default meetings to 20 and 45 minutes, you’re constraining the time to focus on the value-adding conversation.

Set Meeting-Free Blocks It’s all the rage for companies to do meeting-free afternoons or days, and while that may be incrementally helpful, we can’t assume that everyone will use that same time and day every week to be a productivity ninja. You also want to avoid the company-wide cramming of meetings into other 154

Chapter 10

Your Career

parts of the week as that behavior, on mass, creates a different problem. Similarly, sometimes the most value-adding work to be completed is in fact a conversation or meeting, so removing people’s autonomy to do that is silly. Individual meeting-free blocks can help to create time and autonomy but on a cadence that works for you. Maybe it’s an hour every lunchtime to force a break and walk the dog. Or, if you’re in your zone in the morning, block every morning for an hour or two to use that time most effectively on what you need to deliver. These blocks don’t have to be meeting-free. You can absolutely use them for that. But they’re blocks that are used by what you determine, not someone else.

Confirm the Purpose of Attendance Overextending invitations for meetings is the equivalent of cc’ing irrelevant people on emails. It’s not devious, just annoying and unhelpful. If you’re invited to a meeting, especially when there are over four attendees, where you can’t see what contribution you will add, politely ask the organizer to confirm what the meeting is intended to achieve, and if it’s clear you are just an observer to it, you can offer to help with anything specific asynchronously or take on any actions assigned to you that come out of it.

Define the Outcome of the Meeting There’s plenty of literature around about the purpose of meetings and when and where to use them. It’s never that black and white in practice, so something I’ve tried to adopt is making sure I’m clear before a meeting what we hope to achieve by spending time together (where it’s not already obvious) and if there’s anything that can be shared prior to the meeting as a pre-read to make best use of the time. This is especially helpful for “presentation meetings.” Someone has done something and books time to take everyone else through it. If you want to test a new approach to this, a week before the meeting, send out either the presentation or document as 155

Chapter 10

Your Career

a pre-read, or record a short Loom video of yourself presenting what you need to, and set the meeting as being specifically to debate or decide on an outcome. You’ll find it reduces the time needed in the meeting, allows for more reflection and thoughtful responses during the meeting, and allows for others to have a greater sense of autonomy for their time.

If You Do Nothing Else, Do These Three Things This is a really simple habit to help reduce the likelihood you get to the end of the day and you’re not sure what you accomplished. At the start of each day, or the night before, decide on the three things that, even if you do nothing else, you must get done that day. And then test if your calendar that day allows you time to accomplish those. If it does, great! If not, you need to reconfigure your calendar (and time!). Your time is the biggest enabler to how you do your job, so if it’s not working for you, it’s time to change it. You’re welcome for the pun.

Everyone Is a People Expert I said these words to a colleague after coming out of a company-wide forum where I was presenting quite extensive upgrades to a reward and benefit framework. Weeks of research, engagement, and iteration had gone into getting something really exciting in place that would scale with the company, incentivize people, and also continue the journey toward pay equity. Even though I knew it would be iterated several times once live, I was pumped to have it in place. Reward conversations and presentations are always lively, and in this case, it was no different. But from what started as sharing a new framework that would benefit almost every single person at the company ended up becoming comment after comment after comment with sentences starting with “we should be doing…,” “why aren’t we…,” and “my roommate’s company does it this way….” 156

Chapter 10

Your Career

Now don’t get me wrong, I live for lively conversations like these. It’s gold dust for someone in my role to have ideas and engagement on people topics. But in the moment that I walked out of that forum and referred to everyone as people experts, I couldn’t help but wonder what a finance, or legal, or sales presentation would look like with those sorts of comments being made. The People space is full of thoughts, opinions, and ideas. Some of them are from people working directly in that space. But most of them are from folks who simply have a vested interest in the outcome. More than any other function in a company, people feel affected by the decisions that we make. So, quite rightly, we should expect (and want!) for those decisions to come under close scrutiny. The missing piece to this is the gap that often exists between those with feedback and ideas and those who have knowledge and experience in that area. As a graduate, I remember putting my hand up to complete a reward analysis project. I’ve always been incredibly fascinated by the concept of reward in companies and I honestly thought “how hard can it be.” Fairly narrow thinking I know. In the years since, reward has been a critical part of almost every HR role that I’ve had in both big and small companies, and in startups. And the more I work in the reward field, the more I feel intimidated by just how complex and nuanced it is. I felt more of a reward expert as a graduate with no experience, than I do as a C-level People professional with a lot more experience. It was this gap that would result in someone telling the whole company that if we’re serious about pay transparency, we need to share everyone’s salaries within the company, while simultaneously I was receiving private messages from others, including those in my team, who said they felt that idea was unwelcome and uncomfortable. How do we balance and encourage the gift of ideas, criticism, and feedback with the complexity, nuance, and grayness that is almost every part of people and culture? The approach I take lies in the communication of what we’re delivering. It’s not just overcommunicating, but being able to make transparent almost every single part of the thinking, decision-making, 157

Chapter 10

Your Career

and impact of what we’re delivering. We can’t just roll out a reward framework and then be perturbed, like I was, that others would have such strong opinions about it. We have to communicate the intent of the framework, the restrictions, and the constraints that might exist, involve diverse subsections of the team in the process to design it, explore openly the imperfections and edge cases, and be brutally candid with how we arrived at the decision to implement the framework. When we strip away the asymmetry of information, we’ll still have strong opinions on almost everything we do, but we can separate these into items needing further consideration and those that we just need to address head-on.

It’s Great to Experience a Truly Shit Company at Least Once Working in a terrible company is truly a bittersweet experience. It’s bitter 100% of the time you are there, and only months or years later once you’ve left and hopefully found a better company to work with does it start to taste sweet. And that sweetness is rooted almost entirely in the perspective and learning that you now have from seeing browner pastures. I’ve had the good fortune to experience really toxic and unhealthy cultures, and others that exude values and brings the best out in me. The perspective and learning from each has been invaluable and helped to shape a lot of what I now work on. Despite experiencing some really tough moments and emotions during my tenure in toxic cultures, I’m glad that they happened. The perspective I gathered is the ability to identify and be grateful for positive work cultures and great companies. Take cultural traits such as belonging, autonomy, and trust. It can sometimes be difficult to identify traits like these, and the behaviors that drive them, within company cultures unless we’ve experienced them, in some form, before. My recognition and appreciation of companies where I feel like I belong is 158

Chapter 10

Your Career

driven, to a large extent, by what I experienced and how I felt in workplaces where I felt I definitely didn’t belong. The pressure I felt to behave in a certain way, particularly with senior leaders, and the adjusting of behaviors and covering I had to do to conform to this weren’t as identifiable at the time. But once I came into a company where this weight was removed, it became more obvious just how much energy and time I was spending trying to conform to a culture where I clearly didn’t belong. Similarly, the learning you take from toxic cultures, and especially terrible managers, has helped me shape my own leadership approach and work to avoid the repercussions it creates. In the past I’ve needed managers at certain times to meet me where I’m at, be it to unblock some problems I was having, to listen to some feedback, to be candid about something in the business, and even to just give to show they care about something I was experiencing. And I know the impact it had on me when I didn’t have that support from my manager, on both my work and my general feelings about the company. I never want to have that effect on anyone in a business. If you’ve experienced a truly shit company or manager in the past, look for the lessons in what it taught you, as unpleasant as it may have felt at the time. Whether you consciously know you’re doing it, the experience itself has likely given you a heightened ability to sense the behaviors and culture that you experienced. And, hopefully, gratitude to a truly great company and manager when they emerge.

 caling Part 1: Keep Your Team As Small S As Possible Growing startups are feeding grounds for work creation. Regardless of how value adding the new work might be, it is a reality of any company that is growing their product, customer base, and team that the volume and complexity of work is very fluid for a number of years. Within People 159

Chapter 10

Your Career

teams, it can feel like a constant transformation. Small teams without huge investments in people infrastructure yet are balancing the operational delivery of their work with one eye on the direction of the business, and making sure that it’s all aligned. If you add to this a common investment environment where startups are receiving an injection of capital every couple of years (usually with a growth and hiring plan to match), it’s not uncommon to feel that the answer to work creation is to just keep hiring. However, that’s growth. Not scaling. And as the business continues to grow the customer and team base, you’ll start to witness inefficiencies in how the team operates. Communication becomes more complex and takes a lot longer (picture the reward framework presentation from the previous chapter and how that might be different with 500 people instead of 200 people). Work duplication will start to creep in and, unless the business was already profitable through the rounds of funding, the inefficiency will be a barrier to achieving profitability. Culturally, growing like this starts to embed a problem-solving dilemma. To solve problems, the team thinks the answer is to hire. But by continuously hiring, you’re increasing the risk of problems and the impact that they have along with extending the period for which you feel like you need to keep hiring. As a manager of a team, I’ve become quite hell-bent on keeping the team as small as possible for as long as possible. In principle, it sounds achievable. In practice, it’s a bit of a nightmare. I’ll keep using the People team as an example for this lesson, but this lesson isn’t company-wide in terms of the philosophy behind it. It’s applicable across the board. For a People team to stay as small as possible, two things are nonnegotiable.

160

Chapter 10

Your Career

 ork Is Thoughtfully Managed, Not W Just Executed This means that instead of accepting work into the pipeline of things to be done, the work is swiftly assessed to understand the value, impact, and approach. For example, you might be asked by a founder to make sure that any candidate at offer stage has two completed references taken. The natural response is to make it happen and most companies do that, so why not? What starts as very manageable, maybe a couple of new hires a month and two references per new hire, quickly escalates at the next growth phase to be 30–40 references a month. Add to this the constant follow-up of most references as it’s never a quick process, plus the administration of obtaining the reference details, writing up the notes, and storing them on record, and you now have a bloated work process that keeps growing as you do. Let’s take a step back from that. Why do you want references to be completed? Was it the one candidate a founder felt a bit iffy about and wanted some validation? Is it in a customer contract that it’s required as part of their diligence processes? What are you trying to achieve from references, or hoping to avoid? In over a decade of doing reference calls ad hoc for various roles, I can count on my hands the number of times the reference provided insight meaningful enough to contribute to our company’s decision to hire someone. Only one instance was a genuine red flag, and every other one was small nuggets of feedback or insight that proved mildly useful. It’s also risky to assume that feedback from one environment is applicable to the next. After all, I can provide details of a manager who would sing my praises and another who would tear me down. So if we’re going to introduce references for every candidate at offer stage, we need to consider how and if we want to do this rather than just jump right in. If it’s most useful for senior roles, should we just consider references for those roles? If it’s just because of that one iffy candidate,

161

Chapter 10

Your Career

can you do references on an as-needs basis rather than across the board. If it’s an employment verification required contractually with customers or partners, can we outsource it to a third-party integration to automate checks through our ATS? If we’re still feeling pressure to implement reference checks, can you constrain the work to a pilot. Set up a sample of candidates to have references completed, and then at the conclusion of the sample, debrief on both the time taken to complete the checks and the value it added to the company. If it’s justified, great, you have a data point to extend it a bit further. If not, kill it. This process of managing the work rather than just executing it is designed to remove as much work as possible and only keep the most value-adding part to what you’re trying to achieve. And when you look back in a year’s time, doing this across all People team processes might be the difference between a ten-person team and a five-person team, and potentially thousands of hours of low-value work being completed.

Work Is Ruthlessly Prioritized Straight off the bat I want to define what ruthless prioritization means. It does not mean to reorder the to-do list and then go ahead and do everything. It does mean selecting the highest value-adding work to complete and stopping everything else. It’s a minor tweak to mindset, but really important as a scalability factor to allow for teams to stay small and nimble. Ruthless prioritization in a People team is about constantly reassessing the pipeline of work and making a conscious effort to invest resources in things validated to contribute to company goals. It feeds off the thoughtful management of work, but is a broader undertaking as this one requires strong engagement of stakeholders, especially those who influence the People agenda at the company.

162

Chapter 10

Your Career

In one startup, I made a deliberate decision to sequence the investment in the People space in order to focus on the highest valueadding work first. We started with recruitment and onboarding, moved into goals and performance management, built out our reward and recognition programs, and then went full hog on learning and progression. All of these are undoubtedly important in a company, but the last thing we wanted was to need a big team and be simultaneously trying to deliver all of this work. It would be inefficient and overkill based on what the company actually needed. This prioritization meant that some initiatives around were put on ice until other work was completed first, and we needed to communicate that transparently and sensitively. But this also allowed for a very small team to deliver all of this work for a rapidly growing startup and in a sequence that enabled the business to continue to grow.

Scaling Part 2: Make Yourself Redundant This lesson is tightly coupled with the last one so it’s both a logical part two, and also the final lesson in this chapter. This one is personal. It’s a principle I have set with a number of founders and CEOs I’ve worked with and helps drive the intent and behavior needed for the role I was fulfilling. Make yourself redundant. It’s by no means entirely literal, although a small part of me would be quite proud if that was the case (before swiftly realizing it means I’m back on the job market!). Making yourself redundant means an active plan to remove the need of the company to have me or my role as part of it. For a Chief People Officer or similar role I’ve been in, this means delivering work in a way that is efficient and automated as much as possible, building a team that is highly capable of providing the people experience we’ve been aiming for, a culture that reinforces the behaviors and traits needed to succeed in a self-fulfilling and self-enforcing way, and an exceptionally strong leadership culture that aligns all of this with 163

Chapter 10

Your Career

their teams without reliance on the People team. Whenever I join a startup as their first People team hire, it’s because things need building, or are broken, or just need attention. This principle means that I want to be so effective in doing what I came here to do, that I’m no longer needed anymore, and the business can continue to grow sustainably. That’s likely unattainable and for good reason, as businesses aren’t stagnant anyway, but it helps as a mindset to avoid accidentally creating reliance or single points of failure. There is also a natural alignment with this mindset with our own well-being in People teams. One of the initiatives I use each quarter is to reflect on all of the work I’ve been doing and try and think through ways I can either stop that work, automate it, or build it in a way that requires reduced input and time. It means I can simultaneously try and create redundancy within my role and also create capacity to tackle what is coming next.

Summary 1. Change is inevitable. Make sure you have enough breadth in your identity and sense of purpose outside of your job so that if you no longer have that job for whatever reason, you have enough in your life to make sure you wake up the next morning with a sense of energy, purpose, and direction. 2. In new teams and roles, you need to spend more time than you think building clarity on what you’re there to deliver and what you’re not. Otherwise, people will fill that ambiguity with assumptions and guesses based on their own experience, which can be difficult to unwind.

164

Chapter 10

Your Career

3. In startups, most people are working things out as they go, and the first they did something they definitely didn’t know what they were doing. Be comfortable putting your hand up and saying I don’t know and use it as an opportunity to work together to solve a problem. 4. We all need outlets, be it physical, quiet and meditative, social, or something different, where we can go to give ourselves some care and love when things get tough. 5. Protect your time and energy, and be unapologetically ruthless with your time. Consider reducing meeting length, setting meeting-free blocks, ensuring purposeful attendance and outcomes at meetings, and setting outcome lists for each day. 6. The work we do in the People space will always garner strong opinions and perspectives because the impact can be so deep. It requires deliberate, transparent communication to bring out our thinking, constraints, challenges, and approach into the sunlight so we can explore those strong opinions in a more constructive way. 7. Look for lessons from terrible companies and managers. Own your heightened ability to sense the behaviors and culture that made it terrible, and the gratitude you’ll have for when you experience the opposite of that.

165

Chapter 10

Your Career

8. Scaling is trickier than we make it out to be. In the People space, aim to keep the team as small as possible for as long as possible through management over execution, and through ruthless prioritization (i.e., saying no or not yet). Consider how to automate or remove workload over time to free up capacity for new challenges.

166

CHAPTER 11

TL;DR T oo Long; Didn’t Read: A Summary of Text That Was Too Lengthy I can’t remember the last book I read cover to cover, even if it wasn’t in one sitting. It’s not because I don’t like books or think books are interesting. I just don’t have the attention span. Some of the best books I’ve come across and have on my shelf are ones where I’ve read parts of it at certain points when I find them relevant, or I’ve carved it up into small chunks over months. Sometimes, years. I always find myself craving a better book summary or way to make it feel more accessible to me. One where I can get the gist of a book first, before deciding when and where I will dig deeper to further my understanding. So it feels appropriate in this book that I give that a go for those readers who, like me, appreciate a TL;DR to pretty much everything. This chapter collates the summaries of every chapter beforehand into a single list of mental notes, principles, and lessons shared in People Ops.

Chapter 1: Building from Scratch •

Ground your decision-making in data and make it transparent. The goal is not to please people. Good decisions sometimes piss people off.

© Patrick Caldwell 2023 P. Caldwell, People Ops, https://doi.org/10.1007/978-1-4842-9819-0_11

167

Chapter 11

TL;DR

•

Avoid short-term temptations for bespoke employment terms. You’ll build a people debt that comes back to bite you in the ass once you grow.

•

Perfect work rarely delivers materially more value than good work in a startup, so get it done and trust your ability to iterate it over time.

•

Build automation and self-service into as many administrative processes as possible to delay your need to hire and reduce administrative burden.

•

Be clear on how decisions are made and what inputs are needed. Decision by committee is neither fast nor does it result in a higher-quality decision.

•

Every initiative you work on must be aligned to the priorities of the company. Work your way inside-out to understand what people solutions will solve challenges and enable success in each team. And beware magpies!

Chapter 2: Leadership

168

•

Identify areas of the company where there is a lack of leadership capability and accountability, where the wrong leadership behaviors are playing out, or where accidental leaders need safety to move out of their roles.

•

Leadership is hard and not for everyone. Embed into progression and development programs the option to pursue people and non-people leadership roles. If you are in a people leadership role, find that psychologically safe space to share your highs and lows.

Chapter 11

•

TL;DR

We can’t, and shouldn’t, avoid difficult conversations. It’s human for us to be affected by them and that is not a weakness. Sometimes those difficult conversations require us to change tune and show our teeth to get the best outcome for someone.

Chapter 3: Culture •

Culture is a fluid fabric of systems and behaviors. It’s how stuff happens, not what’s in the fridge.

•

Culture fit and culture contribution are currently fighting for attention, but it’s never been an either/or battle. When you’re building your team in a startup, you need to be looking for both.

•

Put a common language around the business and culture as you grow. It helps you work through conflict, focus on culture fit and contribution, and build alignment to goals.

•

You can’t be values-led without a significant trade-off to demonstrate it. Narrow in on the trade-offs you make that demonstrate what your values might be.

•

While process is important at times, overusing it in growth-stage companies starts to chip away at the pace and agility that likely differentiate you from bigger players in the market. Things will slow down and become more structured at some point, so best not to force it prematurely.

169

Chapter 11

•

TL;DR

Reducing the size of your team is a last resort, not a first one. Exhaust every other option first to reduce spend, look for ways to reduce staff costs without losing jobs, and if you need to make that difficult decision to let people go, your people deserve for it to be done sensitively and generously.

Chapter 4: Inclusion

170

•

Representation matters, but it can’t be the sole aim of your DEIB work. Start with inclusion and focus on the pockets of the business at high risk for non-inclusive outcomes (e.g., leadership behaviors, communication and meetings, policies and processes that impact people directly, such as recruitment, leave, and promotions). Getting this right adds credibility to the other work you will need to do.

•

When something is 80% formed in your mind, start sharing it with others for input and feedback. The remaining 20% will allow for buy-in and prevent perfectionist behaviors from delaying something that can deliver value.

•

The DEIB space is flooded with good intentions, but our actions and results leave a lot to be desired. Intentions are worth nothing. We are accountable for what we deliver and the impact it has, which is the standard we should apply to any DEIB work that we see.

Chapter 11

•

The gender pay gap has become a divisive topic but is ultimately a test of so much more in the people space than just compensation. Getting under the skin of what drives it, where inequities exist, and how to right these allows us to tackle the problem at the core, not just try and manage the symptoms.

•

Bias is a normal, unavoidable, and human experience. We shouldn’t be scared of it or try to deny its existence. We should be scared of letting it play out unchecked.

TL;DR

Chapter 5: Recruitment •

So many parts of the hiring process are broken. We have an opportunity to do good by people and offer up a candidate experience with care, speed, and respect at its core.

•

Best offer first principles can drive tangible results and reduce asymmetric information in the offer process.

•

Reframe hiring to be about hiring someone who is a great fit for the role, not hiring the best person from the candidates you’re interviewing.

•

Demonstrate two-way interviews by turning the tables.

Chapter 6: Reward •

Build benefits for the 99% of people who will benefit from and value them, rather than the 1% that abuse them.

171

Chapter 11

172

TL;DR

•

The status quo of hiring without pay transparency has passed its expiry date. We need to prevent asymmetric information and an employer-dominated power dynamic and reduce the inequities in pay discussions that prevent our people from feeling recognized, valued, and fairly treated.

•

It is not black and white to simply say no when someone poses the “pay me more or I’ll leave” ultimatum. There are reasons why it’s sensible to counteroffer and scenarios where it doesn’t make sense, but primarily our goal is to reduce the likelihood from it happening in the first place.

•

Our statutory obligations for benefits and leave are not our benchmarks for good practice. They are the bare minimum we have to do and there’s almost never a compelling reason why we’d ever want to only do the bare minimum for our people. Similarly, to instill trust into the relationship with new joiners early, avoid tenure restrictions on benefit eligibility.

•

We need to bridge the knowledge gap on all things equity, setting realistic expectations, communicating the key components of equity, and allowing our people to have access to a transparent and meaningful way to share in the business’ success.

•

Unlimited leave may seem sexy, but it often proves to have a negative effect. If you do want to rethink leave entitlements, at the very least it should have a minimum amount of leave that allows for both adequate well-being rests and meets any regional requirements.

Chapter 11

TL;DR

Chapter 7: Learning •

Being part of a high-growth startup is a reason to invest in and focus on learning, not an excuse to do the opposite. I typically start with the growth and development culture and nurturing that, nailing onboarding and building a great team of managers to amplify impact across teams.

•

It can be easy to think of learning as a series of online courses, conferences, or reading books. But that’s not where most of the learning actually comes from. Our approach to learning needs to be grounded in experiences for people – tackling new projects, mentorships, learning from mistakes, and stretching responsibilities.

•

Progression doesn’t have to mean promotion, and it will mean something different for everyone. For our work in this space to be effective, we need to understand and tailor our work to how each individual views their own progression and what they’re trying to work toward.

•

Peer feedback is equally as helpful as it is dangerous. We should carefully plan how we build skills in giving meaningful feedback, ensure appropriate and safe forums in which that feedback is provided, and help our people know what to do with feedback too.

•

Not all resignations are bad. There are great reasons to leave a business, and when someone leaves who has aspirations to do things simply not possible in our business, we should be excited for them and grateful for their time with us. 173

Chapter 11

TL;DR

Chapter 8: Performance

174

•

Managing a team can feel overwhelming trying to get everything right and avoid all of the pitfalls you’ve been warned about. It can be helpful to strip it back to fundamentals. If you do nothing else for the moment, make sure you help each person in your team answer these three questions: What am I doing? How am I going? Where am I going?

•

If you’re building a goal-setting process for the first time, don’t be afraid to experiment and don’t be disheartened if you get it wrong. I messed it up a few times, and with each iteration and improvement, it gets closer to a great goal-setting process.

•

There are two truths about people and startups. Number one: people outgrow startups. Number two: startups outgrow people. Both are perfectly OK when we can’t find a path for someone.

•

Swap out your “hire slow, fire fast” mentality for one that is people-first. Hire with purpose. Design a process to test the critical requirements and components of the role that allows for decision-makers to arrive at a conclusion in the quickest amount of time. Fire thoughtfully, as though it was you or a member of your family receiving the news.

•

It can be difficult to know what best practice performance reviews look like, but in my experience it’s the culture of the business and the manager’s behaviors that have the most impact on success rather than the specific design of the performance cycle. Avoid

Chapter 11

TL;DR

forced distribution and deferred feedback, identify and mitigate reviewer bias, and be mindful of how you define ratings if you choose to use them.

Chapter 9: Remote Working •

The Covid-19 pandemic accelerated decades of progress with remote work adoption in the space of 12 months. Now that we’ve come out of the pandemic and greater choice exists, we should expect to be in a teething period for quite some time as we learn more about how various arrangements can contribute to our teams and culture.

•

Remote work has broadened our understanding of how we think about human behavior and performance in different contexts. It also aired our dirty laundry, in particular whether we actually know how to measure performance, how we perceive and build trust in relationships, and the (lack of ) depth in our understanding of culture and what drives it.

•

Be precise in how you describe work arrangements. Remote work and flexible work are two different things, and we should uncouple our thinking on these as being related.

•

A new role has been introduced through the pandemic in many companies – the remote manager. There are three areas, in my experience, where remote managers consistently excel – blending synchronous and asynchronous communication, onboarding, and staying in tune with both work and well-being.

175

Chapter 11

•

TL;DR

While burnout is prevalent and increasing across all work arrangements, remote work has added a new lens to how we identify and respond to unique risks of burnout that it poses, in particular around the blurring between our work and nonwork lives.

Chapter 10: Your Career

176

•

Change is inevitable. Make sure you have enough breadth in your identity and sense of purpose outside of your job so that if you no longer have that job for whatever reason, you have enough in your life to make sure you wake up the next morning with a sense of energy, purpose, and direction.

•

In new teams and roles, you need to spend more time than you think building clarity on what you’re there to deliver and what you’re not. Otherwise, people will fill that ambiguity with assumptions and guesses based on their own experience, which can be difficult to unwind.

•

In startups, most people are working things out as they go, and the first they did something they definitely didn’t know what they were doing. Be comfortable putting your hand up and saying I don’t know and use it as an opportunity to work together to solve a problem.

•

We all need outlets, be it physical, quiet and meditative, social, or something different, where we can go to give ourselves some care and love when things get tough.

Chapter 11

•

Protect your time and energy, and be unapologetically ruthless with your time. Consider reducing meeting length, setting meeting-free blocks, ensuring purposeful attendance and outcomes at meetings, and setting outcome lists for each day.

•

The work we do in the People space will always garner strong opinions and perspectives because the impact can be so deep. It requires deliberate, transparent communication to bring out our thinking, constraints, challenges, and approach into the sunlight so we can explore those strong opinions in a more constructive way.

•

Look for lessons from terrible companies and managers. Own your heightened ability to sense the behaviors and culture that made it terrible, and the gratitude you’ll have for when you experience the opposite of that.

•

Scaling is trickier than we make it out to be. In the People space, aim to keep the team as small as possible for as long as possible through management over execution, and through ruthless prioritization (i.e., saying no or not yet). Consider how to automate or remove workload over time to free up capacity for new challenges.

TL;DR

177

Index A Applicant tracking system (ATS), 65 Asynchronous communication, 142

B Building from scratch communication strategies, 6–8 compensation, 3–4 decision-by-committee, 10–12 decision-making process, 3–5, 10 drive self-service, 9, 10 employment terms, 6 magpies, 12–14 recruitment process, 11, 70, 71, 126 unscalable solutions, 8

C Careers, 147 calendars, 154 communication, 157 make-yourselfredundant, 163–164 meeting-free blocks, 154–155

mentors/coaches, 147 ruthless prioritization, 162–163 time management, 153–154 work acceptance, 161 work duplication, 160 Covid-19, 135–136, 152 Culture autonomy, 35–37 contribution/fit, 32–35 diversity, 43, 51 redeployment, 43 transparency, 34 values, 44 workforce-reduction, 40

D, E Diversity, equity, inclusion, and belonging (DEIB), 50, 51, 54, 55

F, G, H Flexible vs. remote working flexibility, 140–141 hybrid, 140 remote, 139–140

© Patrick Caldwell 2023 P. Caldwell, People Ops, https://doi.org/10.1007/978-1-4842-9819-0

179

INDEX

I, J, K

P, Q

Inclusion, 49 biases, 60 compensation framework, 59 diversity, 47, 50–51 gender pay gap, 55–57 intentions, 54–55 leadership, 51–52, 168–169 pay transparency, 82–88 progression, 58–59 recruitment, 58, 171

Performance deferred feedback, 130–131 forced distribution, 129–130 goals and underperformance, 117–118 hire slow, fire fast, 125–127 mindset/behaviors, 117 OKRs, 120–122 outgrowing startups, 122–125 rating emphasis, 131 review bias, 130

L, M, N, O Leadership accidental leaders, 22–23 accountability, 19 completeness, 19 development perspective, 24 feedback, 28, 29 investment, 17, 19 progression frameworks, 23–24 psychological safety, 24–26 wrong leaders, 21 Learning, 103 career advice, 109–112 growth culture, 104–105 onboarding, 106–107, 142 peer feedback, 113–114 perception, 114 perfect-resignations, 115 progression, 103, 104

180

R, S, T, U, V, W, X, Y, Z Recruitment, 63 best offer first, 68–69 candidate experience, 69–71 comparison effect, 73–74 job application, 64–65 negotiation process, 66–69 transparent salaries, 66 Remote working, 135 burnout, 143–144 Covid-19, 135–136 culture, 138–139 dirty laundry, 136–139 exceptional managers, 141 onboarding, 142 performance, 137 synchronous/asynchronous communication, 142

INDEX

trust, 137–138 Reward, 77 benefits, 78 design, 77–78 dilution process, 96–97 discretionary decisions, 94–96 equity, 93–94 global environment, 92

learning budgets, 78–80 leavers, 96 liquidation preference, 98 Sam’s story, 88–89 team parity, 91 unlimited holiday, 99–100 unrealistic expectations, 94

181