35 Thoughts for New and Aspiring Leaders 9798364517210

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35 THOUGHTS

FOR NEW AND

ASPIRING

LEADERS

MATT STEPHENSON

MATT STEPHENSON

35 THOUGHTS FOR NEW AND ASPIRING LEADERS

Copyright © 2022 Matthew John Stephenson All rights reserved. No part of this book may be reproduced or used in any manner without written permission of the copyright owner except for the use of cited quotations in a review or other relevant work. Kindle edition 2022 Written by Matthew John Stephenson

Also available in Paperback (ISBN 9798364517210) Imprint: Independently Published

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For Kerry, Harry, George and Molly x

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Contents

1. 2. 3.

4. 5. 6. 7. 8. 9.

Introduction

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TRUTH The only thing that stands up to scrutiny is the truth Tell the truth, but reserve the right to change your mind The truth never follows a rumour

8 9 11

TALENT ACQUISITION AND PERFORMANCE MANAGEMENT Don’t wait for talented people to resign to pay them what they’re worth Pay new starters more than they ask for Hire good people and give them clear direction Constantly evaluate talent and poor performance Do what is right for your business, always, but treat people with respect while you do it Separate the scale of the mistake from the scale of the impact and the scale of the response

13 14 15 16 17 19

10. 11. 12. 13. 14. 15. 16.

BEING CREDIBLE Take control of day one Identify the burning imperative Know the numbers (not just your numbers) Talk in plain English Act like a leader, not a supplier Focus on business outcomes Be informed (not just about technology)

21 22 23 24 25 26 27

17. 18. 19.

LEADERSHIP APPROACHES Operate a meritocracy Set expectations – you of others, and others of you Don’t negotiate with terrorists

29 31 33

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20. 21. 22. 23. 24. 25. 26. 27.

28. 29. 30. 31. 32. 33. 34. 35.

If you have to break a deadlock, you won’t please everyone, so make sure the decision you make is right for the business Don’t be afraid of the hierarchy Work wherever and whenever you can most effectively get the job done Embrace failure in the pursuit of excellence Strive to be better, not the best Don’t speculate with authority Prediction is proof A consistent leader is a good leader MISCELLANEOUS THOUGHTS Every resignation is an opportunity You can’t reason with unreasonable people Your team’s successes are your successes There’s no such thing as “IT” and “The Business” All feedback is a gift Passion takes many forms Not every vein is an artery Organisational competence is more important that individual competence

35 36 37 39 40 41 42 43

45 46 47 48 49 51 52 53 54

Conclusion

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Introduction I love a good saying. I really do, I’ve always said it. Anyone who has worked with me knows it. That’s because I believe that they help to cement an idea, encapsulate a belief, or tell a story, and stories help to ensure understanding and secure buy-in. They help demystify technical things for a non-technical audience. They make concepts more memorable. They help people relate to whatever it is you’re trying to tell them. It’s all part of my approach to providing Common Sense Consultancy, rooted in plain English and pragmatism. Many of my favourite sayings encapsulate something about my personal preferences for how I lead, collaborate, and coach. They tell you something about me and my values. In my almost 30 years of working in Technology teams, I’ve been blessed with some phenomenal leaders and colleagues, and many of their values have become my values along the way. In this book I elaborate on some of those sayings, to bring to life my approach to leadership. Each one fits on just one or two pages, so you can dip in and out. None of them is a long essay. Hopefully there’s just enough to spark a thought in your head about whether you agree with me or not. You might not agree with them all, and that’s ok. I’m comfortable with people not agreeing with me, because even if something I’ve written causes you to pause and consider why you don’t agree with me, that’s also a great outcome. My career has been spent in Technology and Technology Leadership, but very few of these sayings have anything to do with Tech and is equally applicable to other spheres of leadership. So, let’s get straight into it…

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35 THOUGHTS FOR NEW AND ASPIRING LEADERS

TRUTH

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1. The only thing that stands up to scrutiny is the truth Over the years I’ve occasionally found myself on the receiving end of explanations for project slippage, outages by third party data centre providers, team restructures, redundancy programmes, changes in personnel, or whatever, that simply don’t add up. When that happens, and you scratch at the surface of the rationale that’s been given, it doesn’t hold water, and the communicator or originator of the message immediately loses credibility. If you’re the one delivering the message, have you ever felt under pressure to give a reason for something that is not entirely truthful, perhaps because you or someone else feels that the truth is unpalatable? In that position, have you then felt the intense heat of scrutiny or questions that peel away the surface of the untruth, and you find yourself struggling to maintain the pretence? It’s uncomfortable, isn’t it? And when the people scratching at the surface realise that you haven’t been entirely truthful with them, the damage done to the trust in the relationship can be irreparable. That’s because the only thing that stands up to scrutiny is the truth. If you tell the truth and someone digs a bit deeper, what they uncover is the next layer of detail on the truth, and it fares well under examination. So, I believe that even if the message is unpalatable, you will earn respect and credibility if you tell the truth. Of course, sometimes there are things that can’t be shared yet, and it’s ok to say that, but you should avoid fabricated excuses to explain a situation, no matter how well intentioned, because eventually the truth will out. If you tell the truth, even if it must be a limited version of the truth, or if the truth is that you can’t share the details yet, it will hold water under scrutiny and your integrity will be intact.

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2. Tell the truth, but reserve the right to change your mind Over the years, before I operated in Senior Leadership positions, I would become frustrated when I could see that something was afoot, but my leaders weren’t communicating. They didn’t share what they were doing, or where the organisation was heading, or what they were thinking, until whatever they were doing was cast in stone and being rolled out. Often, leaders are reluctant to share their thinking until it is well formed and likely to be implemented. They don’t want to share half-formed ideas or options that might not come to pass, because they might appear indecisive, or it might bring some uncertainty to the team. On the other hand, the risk of not sharing anything until it is being implemented is that team members feel that they’re unimportant and that something is being done to them. It builds a feeling of disquiet and reduces trust. Engagement falls because team members feel that they are not being consulted, informed or even considered. My personal preference is to tell the truth but reserve the right to change my mind. Some things are sensitive and can’t be shared, as discussed earlier, but if I’m going to talk about something I talk about it honestly. Some people might say, “but you can’t tell them there’s something going on that you can’t tell them about, because they’ll worry about it”. My counter to that is that if I’m asked a direct question, it is the lesser of two evils to say, “I can’t talk in detail about plans” than, “there’s nothing going on”. They’ll find out soon enough and will respect you more if you were honest with them. This can be a double-edged sword, though, because it can make you appear indecisive if you exercise your right to change your mind often. However, if the change of mind is supported by new information, this appearance of indecisiveness can be countered. In my experience, and having seen both approaches adopted, the benefits of being open with people, especially in response to a direct

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35 THOUGHTS FOR NEW AND ASPIRING LEADERS question, outweigh the downsides. If I can’t tell them, I tell them that I can’t tell them. You’re damned if you do, and damned if you don’t to some extent, but treating people like adults and sharing your thinking as you go along builds engagement and you might even get some input that helps shape a better answer.

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3. The truth never follows a rumour Have you ever noticed that the way a newspaper publishes a correction or apology for an incorrect front-page headline is often to post it in a tiny box on page 7 or 8 of the paper? Corrections of misinformation, or the dispelling of inaccurate or harmful rumours in business are often not robustly executed, either. The truth never follows a rumour. Don’t let this happen! If you’re aware of unhelpful rumours that you know to be inaccurate, correct them. If you’ve been guilty of putting poor information out there, unwind it. Make sure you do it in a way that is as visible and far reaching as the original misinformation. If the misinformation painted someone in an unwarranted bad light (you should be trying to avoid this in any event) make sure that they’re painted in a good light for all to see as soon as possible.

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TALENT ACQUISITION AND PERFORMANCE MANAGEMENT

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4. Don’t wait for talented people to resign to pay them what they’re worth If you are really committed to retaining talent, don’t wait for good people to resign to pay them what they’re worth. Instead, be aware of the market, and make sure your team members are being paid competitively. The objective is to take salary and other benefits out of the equation as far as possible when it comes to retention. It should be a simple hygiene factor, really. Pay people what they are worth in the market and then if they want to leave, it is likely because of something else. Arguably, it will cost you more to retain someone who has resigned than it will do to constantly ensure they are being paid in line with the market. Just the act of reviewing regularly and keeping them in line with the market creates loyalty in many people. Of course, if you can’t afford to pay the market rates, and not all businesses can, you need other strategies for retaining those people. For example, investing in their career development, providing training and development opportunities, and of course, making sure they have interesting and exciting work to do. There will be some people for whom that is more important than money. If you genuinely can’t afford to keep them, then you should also have a clear recruitment strategy that supports the onboarding and development of early-career team members who can then work up through the ranks. It’s entirely reasonably to have a strategy of “up and out”, where you expect a proportion of people to leave after a couple of years to move to bigger businesses or broader roles. That’s fine if you have a pipeline of early-career talent to feed your team with.

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5. Pay new starters more than they ask for You want a new team member joining your team to feel like they have got the best deal they could. If you have a budget that is above what the candidate is asking for, consider offering a little bit more than they’re asking you for, if you think they’re worth it, so that they know they got the best deal they could. Not everyone agrees with me on this, but I think that if you offer someone exactly what they ask for, they can subconsciously think “have I undervalued myself? Should I have asked for more?”. Offering a great candidate a little bit more than they’ve asked for, if your budget can stand it, puts them in a much better headspace to begin with because they immediately think “I’ve got the best deal I could” and “they haven’t tried to get me as cheap as they can, because they’ve offered more than I asked for”. I believe those things buy an extra year of loyalty from many people. Certainly, they won’t immediately be looking at the market again to see if they could have got a better deal.

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6. Hire good people and give them clear direction As a senior leader, you will have a team of people around you who need to do a good job for you to succeed in your role. Often you will inherit a team, but sometimes you will also need to hire into your structure. When you are hiring, it’s important to be clear on the role you need them to do and hire good people capable of executing a strategy that you clearly outline to them. The best people will want to have some say in how things are done, and so it is vital that you’re clear on what you want them to achieve and create an environment where they have some freedom (within a framework) to work out how best to deliver those outcomes. If you micromanage people, they will eventually tire of this and leave (if they’re good at what they do) or they will become order takers, and you will have to tell them what to do forever (if they’re not so good at what they do). Hire the best people you can afford and then give them clear direction. Your role can then be one of strategic planning, providing clarity, unblocking issues, being a sounding board and creating an environment where your team can flourish.

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7. Constantly evaluate talent and poor performance How often in your career have you seen good people become disengaged because either their own value is not recognised or poor performance or bad behaviour in others is tolerated and left unaddressed? Engagement levels drop measurably in good people who feel they are carrying poor performers or badly behaved team members, where those people are not taken to task and managed effectively. I once achieved a 12.5% increase in Team Member engagement (in my first full year, as measured by an outside agency compared to the prior year) despite having put the team under a fair bit of pressure for improved delivery throughput and by bringing some big changes to how they worked to achieve that. I thought they’d found it tough, and I feared that would be reflected in the engagement scores. As you can imagine, I was delighted and surprised by the results. The engagement survey had been anonymous, so I didn’t know who I could ask to get a sense of why the engagement had risen. I asked the whole team if anyone was willing to share some insights with me as to why engagement had improved. The response was that there were a few factors, but most relevant here was the fact that I proactively recognised good performers and robustly managed poor performers or badly behaved team members. They went on to tell me that there are few things more demotivating than seeing someone consistently give less than 100% whilst being rewarded like those people who went above and beyond. By tackling both sides of the coin (good performance and poor performance), the differentiation between them is even greater than just tackling one side.

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8. Do what is right for your business, always, but treat people with respect while you do it As a senior leader, you will, from time to time, have to manage poor performance or poor behaviour in team members. Poor performance and poor behaviour need slightly different approaches. You should be actively managing your team’s performance, and where someone is falling short, consider why it might be. Have they previously performed well? If so, what has changed? Are they in the right role? Have they been promoted beyond their ability? Do they need some training or other support? There are lots of good reasons why someone might be performing badly. It's important that in the case of poor performance, you give timely and constructive feedback. Don’t just tell them they’re doing badly. Be specific and help them understand the impact on the business and team. If you believe they can turn it around, look for ways to help them improve and give them time to do so. However, as soon as you know that they are not going to make it, and you’ve explored the questions about why, act decisively in the best interests of the business. If you know they’re not going to make it, they probably do as well, and you should follow whatever processes are in place to do the right thing for the business, whilst treating the individual with respect. In my experience, nobody enjoys a drawn-out process, least of all the individual concerned, so you might be able to find a mutually agreeable way to bring an earlier conclusion. Poor behaviour is another thing entirely. I have had to manage difficult people who behave badly and make the working lives of other team members miserable. Sometimes, it is because of weak historic leadership from your predecessors. More often, though, where that behaviour is long-lived, it is because the individual is considered indispensable because of their knowledge, and the bad behaviour has been historically tolerated.

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35 THOUGHTS FOR NEW AND ASPIRING LEADERS In my opinion, there is no such thing as “indispensable”. When I find myself in this situation, I give the individual clear, unambiguous feedback that their behaviours are not what they need to be. Then, I get the metaphorical scales out. I balance the value they’re adding against the overhead associated with managing the individual and the disruption / misery they bring to everyone else. When the balance shifts to the point that the overhead is greater than the value, then decisive action is needed.

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9. Separate the scale of the mistake from the scale of the impact and the scale of the response Many years ago, a team member made a very small mistake that had a big impact. That team member’s capability was called into question, and the words “disciplinary action” was bandied around. I intervened because the scale of the mistake, in my mind, didn’t justify the severity of the response. I pointed out several more fundamental mistakes made by human beings in the team. On some of those occasions the people who made the mistakes should have known better, but because the impact was not large, they got away with it and their capability was not questioned. Everyone makes mistakes. From a human perspective, a small mistake with a big impact is still only a small mistake. A big mistake with a small impact is still a big mistake. As a leader, I think it is important to separate the scale of the mistake from the scale of the impact, and take action based on the former, not the latter. Remember, even big mistakes will happen from time to time. Genuine negligence is far rarer than you might imagine. If a mistake is genuinely made, especially in the pursuit of excellence, consider training, quality checks or automation rather than disciplinary processes.

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BEING CREDIBLE

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10. Take control of day one When you start a new leadership role, whether it is in the organisation you already work in, or somewhere new, it is important that you take control of day one. Often when a new leader arrives at a business it is because their predecessor has moved on and there might be some uncertainty and trepidation about who might replace them. Wherever possible, start your preparations for day one long before you get there. It makes it easier for you to have an immediate impact with your new teams and stakeholders. Day one might include an all-hands briefing where you set your stall out in terms of expectations and approach. Alternatively, it might be that you get around all of your key stakeholders and start to create meaningful relationships. In any event, it’s important that you don’t just “drift in and blend in” without any impact. You want people to know that you’re there and that you intend to make a difference. By doing something decisive on your first day or in your first week, you mark your arrival and create a change point that people remember.

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11. Identify the burning imperative Whenever I start a new job or engagement, I look for a way to establish some credibility as early as possible, by identifying the burning imperative. The concept of a burning imperative isn’t mine and it isn’t new. Lots of esteemed publications talk about it, and I’ve found it particularly useful as a technique for establishing some initial credibility with new teams or businesses. A burning imperative is something that needs urgent attention, and which can be tackled relatively quickly. The burning imperative is different in every business. Sometimes it is something that is broken that you feel you can fix quickly, or it is a project that is failing that could be returned to a green status with a different approach. If the problem is team engagement, it might be tactically solving some of their most pressing issues. The common characteristic, though, is that it can be fixed quickly. The reason for this is that it establishes credibility with stakeholders. It is a statement of intent, that things are going to be different on your watch, that people can rely on you to get things done. Early credibility is important, particularly if your role means that you’re going to be asking your team or stakeholders to trust you on some bigger and more impactful initiatives. It gives everyone confidence that you can get things done.

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12. Know the numbers (not just your numbers) Increasingly, the boundaries between a technology leader and other leadership positions within an organisation are blurring. Even the most cursory analysis of the employment market shows that businesses are looking for “commercially astute” technology leaders and “technology literate” commercial leaders. Too often, in days gone by, a technology leader would have a firm grip of the costs associated with technology, but not have a clear grasp of the overall business case associated with the work they do. If you focus on business outcomes, and marry that with a good understanding of budgets, revenue targets and profitability, you will be able to continually assess whether your technology service presents good value for money and a solid return on investment. Armed with that knowledge you can inform your own continuous improvement plans to optimise where you need to make savings, and to focus on delivering the right solutions for your business.

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13. Talk in plain English I’m sure we’ve all come across technology leaders who think that credibility is gained by bamboozling the audience with technological jargon. After all, if the audience doesn’t understand what they’re saying, they can’t challenge it, and they’ll assume the tech leader in question is incredibly knowledgeable, right? Wrong! Almost exclusively, the technology leader who bamboozles the audience very quickly loses their support. Instead, good technology leaders focus on making complex technical problems simple for an audience. They look for analogies and metaphors, they tell stories, and they check understanding as they go along. If you can demystify technology for a non-technical audience, you will find that people value having you around and will want to engage with you. The ability to bridge the gap between technology and other business disciplines is rarer than you might think. If you have that skill, use it often, because it will set you apart from many other leaders in technology.

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14. Act like a leader, not a supplier Many businesses and business leaders still view their technology function as a subservient supplier to the business. And yet, there are very few businesses today that could continue to operate without technology. I can certainly remember in my lifetime, working in the insurance sector, a time where if a computer system that supported a branch failed, the insurance agents could revert to paper processes and still get the job done (albeit less efficiently). That simply wouldn’t be true today. So, for a business to consider a function that is critical to its day-to-day operation as anything other than an equal voice at the table, is incredibly short sighted. Some technology leaders perpetuate this situation, especially when joining a new business, by behaving like a supplier in a misdirected attempt to establish some early credibility. It links to identifying the burning imperative. When you choose the thing that you are going to do or fix quickly to establish early credibility, don’t choose the thing that sets your stall out as being a supplier rather than an equal. For example, don’t become known too quickly as “the person who can sort out your broken laptop” or “the person who can get you a better phone handset”. Unless, of course, broken laptops and bad phones are demonstrably an inhibitor to the business, in which case the burning imperative isn’t to replace those things, but to solve the problem those things are symptomatic of. Instead, establish yourself from day one as the person who can turn the dial on business metrics through the better application of technology. If someone is struggling to get a broken laptop replaced, find someone in the team who can help with that, by all means, but then look at the processes that created the problem of not being able to get it replaced or repaired, and then fix that process.

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15. Focus on business outcomes Good technology leaders aren’t solely focussed on technical delivery. They should always have an eye of delivery of value into a business. Being very clear on the business outcomes to be achieved helps to keep technology projects on track. It can help avoid scope creep and is a useful tool in prioritisation. It stops you from deviating from a goal, especially if the project is long. It is useful to continually challenge yourself and your stakeholders with questions like, “how does that feature that you are asking for contribute to the goal? If we didn’t do it, of what detriment is it to the overall value in the product?” It’s important as well when choosing the solution to deliver. There’s little point in spending £1m delivering a solution that will only generate £10k of annual revenue. You won’t get your money back in any sensible timeframe. Focussing your team on business outcomes resulting from the work they’re doing also helps to keep them connected to the business. Understanding why what they’re doing is worthwhile is a great motivator. Successful delivery in support of business success is demonstrably beneficial for team engagement. It also reinforces your credibility as a leader with other parts of the business, with your peers in the leadership team and with their teams as well.

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16. Be informed (not just about technology) If you’re a leader with a seat at the executive table, board meetings will cover a lot of ground, much of it having nothing to do with technology. If you only know about your own domain, then your contribution to much of the discussion at your leadership meetings will be suboptimal, and as a collective, the leadership team will be less effective. This situation can also exacerbate any issue with being perceived as a supplier to the business, because your contribution is narrowly framed as one of service delivery. On the other hand, if you make it your business to know about the commercial performance and challenges, the financial position and targets, operational matters of the day, and what is happening with your competitors and the broader market, you’ll have something more valuable to add to the mix by identifying implications or opportunities that might be associated with your own domain when considered alongside those other areas. This makes for a much more rounded conversation and a stronger leadership team. Invariably, better decisions are made by a collective of people from different disciplines, if they can each support and challenge their colleagues at a meaningful level of detail.

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LEADERSHIP APPROACHES

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17. Operate a meritocracy Some leaders are successful by operating an autocracy (or worse, a dictatorship), achieving results by telling people what to do and making every decision based on their own experience. Other less decisive leaders go to the other extreme and operate a complete democracy, where all decisions are made collectively and after much discussion. I’ve seen the autocratic leadership approach deployed with initial success, but it is hard to sustain because good people get tired of being told what to do, rather than being given a framework of responsibility within which they can grow, make decisions, make mistakes, and become better at what they do. And then they leave. New people come in and the cycle starts again. Those people who don’t leave become downtrodden and disillusioned and aren’t productive. Often, autocratic leaders are particularly hard to work for as they leave a trail of devastation behind them as they drive through their ideas and ideals which means that short term success leads to long term disengagement. The other extreme, with everything being democratically agreed is also tricky, because agreeing everything by committee can result in decisions that aren’t optimal for the business because they try to be all things to all people, and becomes soft around the edges. I prefer to operate a meritocracy. I take the view that in any team where my knowledge is a mile wide and a foot deep, the people working in the different disciplines within my teams are likely to have deeper knowledge than me in their areas of expertise. After building that team, why wouldn’t I listen to them? It is imperative that those team members get to demonstrate their skill, given their input, and feel like they’ve been heard. That breeds engagement and gets the best out of the team.

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35 THOUGHTS FOR NEW AND ASPIRING LEADERS Eventually the time for discussion is over and you will need to make a decision, but in a meritocracy, you should be well informed, having taken expert views on board, and you will make a better decision. Sometimes there will still be conflict, at which point you need to step in and break the deadlock. If you fail to create a meritocracy, you risk causing three problems. Firstly, you’re inhibiting the scalability of your business because your own capacity is finite. Secondly, good people want to be heard and have influence. If they aren’t heard and have no influence, they will become disengaged and leave, weakening your team. Thirdly, you’re probably not an expert in everything, so you won’t necessarily make all of the best decisions.

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18. Set expectations – you of others, and others of you This is so important. Whenever I start a new role or engagement, if the success of that engagement requires teams of people to do work under my leadership, I get them all together as part of taking control of day one, to set out my stall. I usually talk about my leadership style, much of which is encapsulated in this book. Part of the process of setting out my stall is to set expectations. Expectations cut both ways, of course. I make it very clear what I expect of people in my teams, but in return I tell people what they can expect of me. The specifics might vary slightly depending on the assignment, but a typical set of things I expect from my teams might be:       

Make stretching but achievable commitments and strive to meet them. Do your best every day. Be honest and have integrity. Take accountability – it is ok to make mistakes in the pursuit of excellence. Play fair – give credit where it is due, celebrate success. Operate as a team – support and challenge your colleagues. Embrace change.

What teams can expect from me:       

Clear direction. Support. Issues unblocked. Credit for skills and experience. Poor performance and behaviour managed. Talented and motivated people endorsed and developed. Timely feedback given.

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35 THOUGHTS FOR NEW AND ASPIRING LEADERS The best time to set these expectations in right on day one, before you have any first-hand experience of the team. It is really easy to say “I will be tough on poor performance” when you have no prior first-hand knowledge of the team. If you leave it until later, it is harder to say without looking at the people you are talking about, or having the team feel that you have an agenda.

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19. Don’t negotiate with terrorists People who think they are indispensable, and choose to exploit that for their own ends, are toxic. Don’t negotiate with them. I can recall a handful of cases over the years where people who considered themselves indispensable attempted to exploit that by making unreasonable demands. To be clear, I’m not talking about those people who make reasonable requests because they’re not being rewarded or recognised appropriately for their contribution. You must try to do something to help those people. I’m talking about the people who seek to exploit their perception that you can’t live without them by making unreasonable demands. When someone does do that, unless you absolutely can’t afford to lose them immediately, don’t negotiate. It sets a precedent, it breeds discontent elsewhere (because they will tell someone that they got a better deal out of you), and they almost certainly aren’t anywhere near as indispensable as they thought they were. On none of those occasions where it has happened to me, and those people have left the business, have we fundamentally failed. Short term pain, perhaps, but never a fundamental derailing of our plans. I recall an occasion where I had a team member who felt they were indispensable. They spent a period of time becoming unhelpful and undermining. Eventually, they resigned and gave one month’s notice. However, their contractual notice period was three months because they had accepted a pay rise linked to a change in Terms and Conditions a couple of years earlier, but they never signed their new contract. They had enjoyed the benefits of the change in terms and conditions, though. As they’d never signed the contract, they exploited the out-of-date contract held on file and secured a letter from HR confirming they could

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35 THOUGHTS FOR NEW AND ASPIRING LEADERS leave in a month. When I tackled them on this, they offered to work the additional two months as a contractor on a day rate. I politely declined and asked them to leave straightaway. They were shocked, but I didn’t want someone with that exploitative personality, who had already become unhelpful and disengaged, in the team a moment longer. The team thrived. Teams usually do because team members step up and filled the void. Some of the team told me that they had felt oppressed and undermined by the individual who had left and relished the opportunity to show what they could do without them. Of course, you may feel that the person in your team who behaves like this genuinely is indispensable, in the short term at least. In that case, talk to them about it, explain the impact and make clear that something needs to change. If they’re unresponsive, start a mitigation plan so that when the overhead of managing them starts to outweigh the value they add, you have options.

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20. If you have to break a deadlock, you won’t please everyone, so make sure the decision you make is right for the business As a leader, you can’t keep everyone happy all of the time. A key part of leadership, and one of the times where a hierarchy is needed, is to break a deadlock. If two or more options are available in any decision, and each has support from some quarter, it is the role of the leader to promote a climate where everyone gets the chance to be heard, but if a consensus isn’t reached, you will need to step in and take accountability for breaking the deadlock. In this situation, by definition, you will have to choose a course of action that doesn’t please everyone. If you aren’t going to please everyone, you may as well choose the course that is best for the business. Don’t worry about upsetting some people – whatever you choose will result in that. Don’t choose the route based on who shouts the loudest. Don’t choose based on who you like best. And don’t choose the easy option, just because it is the easy option (do choose it if it also happens to be the best option having balanced and considered all available data!) Choose the route that, based on the evidence and argument presented, makes the most sense for the business. The route that meets the most objectives, creates the better opportunities, has the greatest chance of success, and so on. Be clear about the rationale for your choice, and then take accountability for the decision. If you have to step in to break a deadlock, it is often true that there isn’t a lot to choose between the options – there’s no right or wrong answer, just a collection of benefits and disbenefits to buy into. Be clear about what they are and follow through with your decision. There’s nothing worse than breaking a deadlock indecisively.

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21. Don’t be afraid of the hierarchy Having the courage of your convictions is a skill, which when combined with the skill of putting your point across the right way, even if it is a contrary or contentious point of view, strengthens any team. You don’t have to hold your tongue, just because a more senior person is in the room. You don’t have to defer to their point of view if you don’t agree with it. As long has you have a reasoned argument and put it across the right way, you should be unafraid of making the challenge. Good leaders will welcome it. Focus on what you want to say, and importantly, how you want to say it, in order to make your point in a professional and compelling way, and you should have no reason to fear the hierarchy. A good hierarchy exists to break deadlocks, to provide support, to set direction. It isn’t there to prevent team members from “lower down” the hierarchy from expressing a view. The best hierarchies are ones where their existence is only felt when one of those hierarchical outcomes is needed (broken deadlock, support given, direction set). This was one of the single most important lessons I learned that unlocked my ability to progress my career. By learning to be confident challenging the point of view of my senior stakeholders, in a way that was respectful and considered, I was increasingly asked to contribute to strategic conversations which paved the way for my own career in strategic leadership.

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22. Work wherever and whenever you can most effectively get the job done The Covid Pandemic of 2020 (and beyond) forced everyone who was able to work from home to do so. The world was probably heading that way, but Covid certainly accelerated it. There aren’t many positives to come out of those times, but arguably one good thing we have learned is that it is possible, for some businesses and some roles at least, to be as productive or more productive working remotely than going into an office. The Pandemic also caused many people to evaluate their priorities and consider what they really wanted from their lives. Many people realised that they wanted greater flexibility to be able to balance work and home life for their general physical and mental wellbeing. Team member expectations of their employers have changed in the post-Covid world. People expect more flexibility about where and when they work, and the businesses that embrace that are likely to fare the best in terms of team member engagement and retention. It’s very easy to fall into the trap of equating “flexibility” with “working from home”, but that is only once facet. Arguably, working from home in and of itself is not the thing that unlocks greater flexibility. Some people will tell you that working from home has made it harder to strike a good work / life balance, because the loss of a hard boundary of a daily commute means they work an extended working day. True flexibility comes from being clear on the outcomes that are needed for a business to be successful and then trusting people to work hard to achieve those, whilst also managing their own well-being. For example, in a traditional 9am to 5pm day, 5 days a week, you would probably have to fit exercise into your early mornings or late evenings, impacting on time at home with your family. In a more flexible world, you

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35 THOUGHTS FOR NEW AND ASPIRING LEADERS might choose to take your exercise in the middle of the day, having spent the time you would normally spend on a commute doing some work instead. Another example of true flexibility might be that you pause your day’s work at 3:30, to do the school run and have a meal with your family, before resuming your work when the children are in bed, completing tasks that don’t depend on the availability of other team members. The key point about flexibility is that it isn’t defined by a set of prescriptive rules. Because then it isn’t flexibility, it is just a different set of constraints that might not work for everyone. My mantra is “work wherever and whenever you need to in order to get the job done most effectively”. Sometimes that might be getting together with the team in the office or some other convenient location. Other times it might be working remotely. Some tasks might be just as productively done in the evening rather than the core day. Don’t arbitrarily require people to be in the office 2 or 3 days a week, just for the sake of it. It implies that working at home is a perk, when the reality is that it is a very demanding way of working in its own right. That arbitrary mandate will just frustrate people who feel that when it is “their turn” to be in, they take on the commute and then do nothing different to what they would do if they were at their desk at home. My own view is that being at a desk in an open office, conducting video calls with people who are still at home is more distracting and less productive than doing those calls from home. If you do feel it is important for people to be in the office 2 days a week, make sure it is when lots of other people will be there, and with the goal of doing something purposeful and collaborative that is better done in the office. Of course, it is also important to note that some people might prefer to be in the office all the time, and that’s ok too, because in a genuinely flexible environment, that is accommodated as well.

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23. Embrace failure in the pursuit of excellence If you have never failed, you’re not trying hard enough. This is a view I subscribe to wholeheartedly. It ties in with the idea of making stretching but achievable commitments and then striving to meet them. By their very nature, not all stretching but achievable commitments will be met. But that’s ok because the alternative is to make easy commitments and meet them all. However, if you want your teams to make genuinely stretching commitments, they need to know that if they fall a bit short, you’re going to be accepting of that, and have their backs. This is a cultural point. There needs to be a culture where you expect failures to happen, not because the team has failed to perform, but because they have truly stretched themselves in the pursuit of excellence.

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24. Strive to be better, not necessarily the best Aiming to be the best in your market, beating all competition, is admirable, but can result in the wrong behaviour or focus. Sometimes, it is ok (and more realistic) to be a strong second or third if the market size supports more than one successful business. It’s obviously good to track where you are in your market but having such a prescriptive and finite goal as “being the best” is fraught with difficulty. For example, “best” by what measure? Are you measuring by revenue, or market share, or profitability, percentage growth year on year, customer satisfaction scores? There are lots of measures. And once you are the “best” (by whatever measure you’ve chosen) where do you go next? You have to maintain your position, but what is the next goal? Worse still, what if you don’t become the best? That doesn’t mean you’ve failed as a business, but you and your teams might feel that you have. Instead, focus on continuous improvement, so that your goal is always to be better than you were before. You can always be better. You can’t control what the competition is doing, but you can control what your business does. If you set improvement goals and metrics rather than finite ones based on a rank amongst your competition, then you’re competing against your own prior performance, and you can always do better.

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25. Don’t speculate with authority I have lost count of the number of times I have had team members speak with absolute confidence about something that later proves to be wrong. Often it is because those people lack critical problem solving skills that I believe are essential for good technology service delivery. Another characteristic of this problem is that they make assumptions. A technique I have learned through the years is to ask people to prove everything. I once worked with a data centre partner who was on a call with us diagnosing why our entire server estate decided to power itself down without warning. We lost service for every customer for an uncomfortable amount of time. We were looking at a graph of server behaviour when the power had cycled and one of the tech guys from the data centre said, “there’s your problem, right there. The servers rebooted themselves right after you made that change.” He then moved on to explain with absolute confidence how what we had done had caused the servers to reboot themselves. I wasn’t buying it, and I asked him to go back to the graph. “Just drill down into the point where we could see the power fail”, I said. When he did, we could see in the detail that the time of the power failure was days after the change we had made. I asked him whether that made a difference to his very confident explanation. Of course, it completely disproved his theory. It's ok to speculate when trying to find root cause of a problem but be clear that it is speculation.

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26. Prediction is proof Issue resolution can be tricky. Succumbing to the temptation to latch onto an early hypothesis based on an initial observation, sinking hours of time in attempting to fix a problem that doesn’t really exist (and then still seeing the issue afterwards), is commonplace. This is something I often say when I’m helping my teams solve problems. It is especially relevant when trying to solve a problem in software. I believe that if you can confidently and repeatably predict the outcome of a software interaction, then it is “a thing”. So, I encourage my teams to prove it. If they come up with a hypothesis that appears to carry weight, I ask them to predict the outcome from interactions designed to test the hypothesis. When they can predict the outcomes with confidence, then I in turn have confidence that they are on to something. If any of their predictions fail they’re unlikely to have found the answer to the problem. This approach works equally well when being applied to the assessment of someone’s behaviour. I once had a team member who had been using fake meetings to create opportunities to avoid doing work. When I began to suspect something was amiss, I looked that their diary for those days I was concerned about. I noticed a pattern where the meetings I was concerned about were created early in the morning of the same day, had a title that suggested they were meeting with someone specific, but that person was not actually invited to the meeting. Once I had identified the pattern, I then began to predict the outcome of looking at other calendar appointments. I chose some appointments that I felt were genuine, and they did not follow the pattern. Then I chose some where I felt they were fake, and without exception they followed the pattern, so I knew I was right. When confronted with the evidence, the team member admitted they had been doing it.

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27. A consistent leader is a good leader How often have you heard it said of a leader, “he blows hot and cold” or “try to catch her on a good day”? We’re all human and even the best leaders can have bad days, but if you’re the sort of leader about whom that sort of thing gets said, then it may be that you’re lacking in consistency in your approach to leadership. It is a skill to leave your troubles at the door, but it is an essential one if you want to create an environment where people feel they can approach you for advice, guidance, to discuss problems, or seek your input into key decisions. Consistency is key, even if personal styles vary wildly from one leader to another. The ideal scenario is to be authentically fair and balanced. Whether your natural style is robust, or laid back, collaborative or directive, be consistent. That way people don’t need to work out whether you’re having a good day or not before approaching you. The best leaders I have worked for over the years have been consistent, regardless of whether our individual styles aligned or not. I’ve seen some leaders over the years where if they’re having a bad day, or the business is having a bad week, then everyone else has a bad day or week. The best leaders work hard to let their teams have a good day or week regardless of how they themselves are feeling. After all, why would a leader in a business that is having a bad week want their team members to be having a bad time as well – that’s not going to generate the best work and good remedial outcomes.

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MISCELLANEOUS LESSONS

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28. Every resignation is an opportunity What’s that? Every resignation is an opportunity? “What on Earth do you mean?”, I hear you cry! Nobody likes it when good people leave. As a good leader, you will, of course, have developed good people along the way, people who want to stay with you and grow their careers in your team. So, when they decide to leave, they are probably leaving for reasons outside of your control. Hopefully. You should try to retain good people, of course, but sometimes it is unavoidable that they want to move on, and it might even be the right thing for their own careers. When that happens, look for the opportunity in it. Don’t always assume that you need to replace that person like for like. Think about your broader needs in the team. Is there a role you need to fill that is more pressing than replacing the person who is leaving? Did that person have gaps in their knowledge or capability that you can now seek to fill with a new hire? Do you need to replace them at all? Could the work be distributed fairly amongst the rest of the team without overburdening them and realise a saving for the business? You can’t always control the fact that someone is leaving. What you can control is your response to it. Look for the opportunities the resignation presents.

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29. You can’t reason with unreasonable people Sometimes you will come across people who are unreasonable. People that are single-mindedly focussed on a particular outcome, objective, point of view, or whatever. You don’t think they’re right, but they won’t engage in a conversation about it. You try to reason with those people. You use evidence and wellconstructed arguments. You bring in previous experience, and the opinions of experts. You do all the things that you should do to try to influence someone, but they are unwilling to accept that they might be wrong. They, on the other hand, have little evidence and present a poorly constructed argument. And yet they steadfastly maintain their position and refuse to budge. Sometimes there comes a point where you must accept that you can’t reason with unreasonable people. In that situation, if you are in a leadership or management position, and it is within your remit, you can decide to overrule, and own the decision whether it ultimately proves to be a good one or a bad one. If you’re not able to make the decision yourself, and someone else is, you can use your evidence, experience, and experts to persuade them to make that decision instead. If the person who is in the position to make the decision happens to be the unreasonable one, then all you can really do is make sure you’ve made your case and been heard, then get behind the team to react to the outcomes that prevail after the unreasonable person has made the potentially bad decision. And of course, you should always be open to the idea that you might be wrong and avoid becoming that unreasonable person yourself, by being open to challenge and recognising that you might not always be right.

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30.Your team’s successes are your successes The more senior you get, the more your own successes are achieved through what your teams do, rather than what you directly do yourself. If you’re in a senior role in technology, you will probably, at one time in your career, have been expert in something technological. Whether you started in software, hardware, networking, infrastructure, or whatever, there’s likely to be an area of technology where you’re most comfortable. But to be a good technology leader, you need to take accountability for a load of other areas as well, where your expertise is less deep, where you know enough to provide strong support and challenge to your teams, but perhaps not enough to be a practitioner in it in your own right. Sometimes people talk about whether your knowledge is a mile wide and a foot deep (you know something about a lot of things), or a foot wide and a mile deep (you know a lot about a smaller number of things). As a good leader, you probably fall into the former category, which is why the most successful technology leaders have built a great team of people around them who fall into the latter. You’ll produce fewer “things” yourself and instead clear the way for your teams to deliver for you. This requires something of a mindset shift, but the best leaders recognise it and focus on making sure their team members collectively have the right skills, they feel engaged, empowered, and influential, and have clear direction and goals.

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31. There’s no such thing as “IT” and “The Business” This is a real pet hate of mine. How often have you heard people talk about “IT” and “The Business” as if they’re different things? Particularly when I have been in permanent roles, I have drilled it into teams that we’re not to talk about “IT” and “The Business” as separate entities. We’re all part of the same business. We share the same successes. We feel the pain of the same failures. In any case, it is just too vague to say, “let’s ask The Business”. Who? Finance? Commercial? Operations? HR? It is meaningless. Instead, I encourage my teams to talk about “Commercial Stakeholders” or “Finance Colleagues” and “Technology Team Members” – or whatever more specific descriptions they want to use to differentiate them. To do anything else perpetuates the idea that IT is something separate to the rest of the business, like a supplier. The reality is that the best decisions get taken by businesses when there is a level playing field on which all functions play. Technologists don’t necessarily have all the right answers, nor do they fully understand the pain that commercial stakeholders feel when trying to sell. Equally, commercial stakeholders are frequently oblivious to the difficulties associated with maintaining a high level of service in technology. Don’t even talk about “IT and The Business” being a partnership. It’s like saying “Sales” and “Finance” are a partnership. All functions are part of the business, not in partnership with one another.

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32. All feedback is a gift People find it hard to give feedback if it is in any way seen as negative. It often gets badged as a “difficult conversation”. I try hard in my teams to create a climate where feedback is welcomed, or even expected. If feedback is given the right way, and with good intentions, it is never a difficult conversation. It is critical that the culture of feedback applies to positive feedback as well as negative. If you create a culture where all feedback is shared, the negative feedback is usually more readily received by others. There’s a way to give it, of course. It should rarely be personal, and it should always be specific and backed up with examples and facts. Even if the feedback is personal, it can be done tactfully and with a good heart. It also helps if you have an attitude that you want to receive feedback. A combination of someone who wants to receive feedback and someone who tries to give it kindly is very powerful. All feedback is a gift. Even if you don’t agree with it, you get an insight into how someone else views you or what you do, and someone’s perception of you is their truth. No matter how well intentioned, useful, accurate and nicely packaged your feedback, there is a chance that the recipient takes it badly. So, make sure you’re in a place where it can be given, explained, and discussed without interruption, and without having to be cut short (definitely don’t give the feedback just as you’re leaving the office for the day or before going off on holiday!). Don’t be ambiguous, don’t beat around the bush. Make it specific. Prepare for the conversation by asking yourself things like, “what do I want to say?”, “why does it matter to me?”, “how will the recipient feel after I give the feedback?”, “what outcome do I want to achieve?”, “what needs to be different afterwards?”. Make sure you have concrete examples so that the person receiving the feedback has something to work with to improve.

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35 THOUGHTS FOR NEW AND ASPIRING LEADERS If you’re on the receiving end of feedback from others, be open to it. If it is delivered in the right way, you might find something useful in it. If you don’t like the way it is given, try not to react negatively. Try to separate what they are trying to say from how they say it. What was the message they tried to get across? If you’re not sure, ask questions to understand their point of view. If you don’t agree, don’t tell them they’re wrong. Explore it with them to understand why they feel the way they do. You might still feel that you could modify your behaviour to recognise that something isn’t right for them. Whether you’re giving or receiving feedback, do it in the right way and there’s almost always value to be found.

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33. Passion takes many forms I’ve often heard it said that someone “lacks passion”. Sometimes it has been true. Often, though, it isn’t. Passion takes many forms, and the way one person demonstrates or feels it isn’t necessarily the same way that you or someone else does. The word “passion” is often used as a synonym for “energetic and excitable”. In fact, passion just means that someone has a strong emotional feeling about or reaction to something. Something they believe fervently in, something they are determined to do or get done. The outward display of the passion could just as easily be a quiet, focussed drive to achieve the goal. Don’t assume that if someone’s personality is laid back, quiet, calm, or reflective, or if they simply don’t demonstrate the outward signs that you personally consider to be “passion” that they are not themselves passionate about something. Also, remember that different people find their passion in different places. Just because someone doesn’t share your passion for a particular thing, it doesn’t mean they will do a bad job for you.

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34. Not every vein is an artery The bigger the teams you lead and the more work they do, the harder it is to keep a finger on the pulse of every initiative or issue. It can be hard for leaders who have grown those teams from a small start to a larger size to step away from the detail, and they try to stay close to every initiative. That isn’t scalable or sustainable. It can be damaging because that leader becomes a bottleneck. It is important that part of the plans for growth in a team include putting in place a strong management team with domain expertise who can take some of the load off the leader’s shoulders. Having said that, team growth doesn’t mean that you step away from everything. Your role as a leader evolves to be one where you have to ensure that your teams are staying aligned to the strategic direction you have set out. Your role is also to contribute to the initiatives that are particularly important. The skill is to know which things need your focus and attention when trying to keep your finger on the pulse, because not every vein is an artery. The arteries are the ones you need to identify, because if they fail, you will feel some real pain (I’m not a doctor, so please don’t scrutinise this analogy too much – I know veins are important a well!). How do you identify which things are arteries? It’s tough because every initiative should have a solid business case and could be considered important. When I’m trying to work out which initiatives to stay close to, I think about these things. Are they:    

Strategically important Commercially valuable Particularly risky or complex Politically charged

I ask myself, “if this initiative goes wrong, is it going to cause us a lot of pain?” Those are the ones I stay close to.

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35. Organisational competence is more important than individual competence Organisational competence is the combined level of skill across your whole team. When you lead teams, and need to hire into them, it is important to ensure that you’re growing your organisational competence. You should maintain some level of understanding about the skills in your team, and the skills gaps. The goal is to have breadth and depth of skill in your team, recognising that not every individual team member needs to be at the same level of skill in every discipline as the others. Also, you might find that it is better to have a few people at a moderate level of skill rather than only one or two people with a high level of skill in any particular discipline, because it makes your organisational competence higher and has fewer key person dependencies. For example, you’re building a software development team, and you need to be able to do full stack development. You might find a lot of great candidates, and while they’re all capable on paper, they all prefer front end development. If you filled all your vacancies with them your individual competence would be high in front end development, but your organisational competence in full stack would not. An appreciation of your organisational competence also helps you build a team with members at different stages in their careers, which creates a succession hierarchy and helps you maintain a resilient team.

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Conclusion I hope this book has given you some food for thought. I said at the beginning, that it’s ok for you not to agree with me on some of this stuff. If you disagree, but it has made you stop to consider why you disagree, that’s great, because we all have different styles and preferences as leaders. If you’re a new or aspiring leader, perhaps this book has given you some ideas for how to think about changes you will need to make to your own style and relationships with teams, because stepping up to leadership undoubtedly needs some different behaviours compared to when you were in non-leadership roles. In any event, thanks for reading. I’d love to hear what you think about the book, so please feel free to drop me a line at [email protected], because all feedback is a gift!

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Whether you’re a new leader or you aspire to a role in leadership, each of the 35 short conversation starters in this book describes the author’s point of view and experience on subjects such as the importance of truthfulness, managing poor performance and top talent, tips for establishing credibility with your teams, and a collection of other observations made over the course of a 30 year career working with, and leading, amazing teams.

Matt Stephenson has worked in Technology for nearly 30 years and has been in leadership roles for around half of that time. He has led teams of between 5 and 150 people and has formulated his approach to leadership in industries as diverse as Insurance, Automotive, Aviation, online retail, online comparison, and Big Data. His Common Sense and pragmatic approach to leadership has served him well as he seeks to help businesses make the most of their technology and teams.