The Engineering Executive's Primer: Impactful Technical Leadership 9781098149482

Table of contents :
Preface
What This Book is Not
Navigating This Book
Clarifying Terms
O’Reilly Online Learning
How to Contact Us
Acknowledgments
1. Getting the Job
Why Pursue an Executive Role?
One of One
Finding Internal Executive Roles
Finding External Executive Roles
Interview Process
Negotiating the Contract
Deciding to Take the Job
Not Getting the Job
Summary
2. Your First 90 Days
What to Learn First
Making the Right System Changes
Tasks for Your First 90 Days
Learning and Building Trust
Create an External Support System
Understanding Organizational Health and Process
Understanding Hiring
Understanding Systems of Execution
Understanding the Technology
Summary
3. Writing Your Engineering Strategy
Defining Strategy
Example Strategy
Diagnosis
Guiding Policies
Coherent Actions
Writing Process
When to Write the Strategy
Dealing with Missing Company Strategies
Establishing the Diagnosis
Structuring Your Guiding Policies
Maintaining Your Guiding Policies’ Altitude
Selecting Coherent Actions
Shouldn’t Strategy Be Bottoms-Up?
Summary
4. How to Plan
The Default Planning Process
Planning’s Three Discrete Phases
Phase 1: Establishing Your Financial Plan
The Reasoning Behind Engineering’s Role in the Financial Plan
Why Should Financial Planning Be an Annual Process?
Attributing Costs to Business Units
Why Can Financial Planning Be So Contentious?
Should Engineering Headcount Growth Limit Company Headcount Growth?
Informing Organizational Structure
Aligning the Hiring Plan and Recruiting Bandwidth
Phase 2: Determining Your Functional Portfolio Allocation
Why Do We Need a Functional Portfolio Allocation?
Keep the Allocation Fairly Steady
Be Mindful of Allocation Granularity
Don’t Over-index on Early Results
Phase 3: Agreeing on the Roadmap
Roadmapping with Disconnected Planners
Roadmapping Concrete and Unscoped Work
Roadmapping in Too Much Detail
Pitfalls to Avoid
Planning as Ticking Checkboxes
Planning as Inefficient Resource Allocator
Planning as Rewarding Shiny Projects
Planning as Diminishing Ownership
Summary
5. Creating Useful Organizational Values
What Problems Do Values Solve?
Should Engineering Organizations Have Values?
What Makes a Value Useful?
How Are Engineering Values Distinct from a Technology Strategy?
When and How to Roll Out Values
Some Values I’ve Found Useful
Summary
6. Measuring Engineering Organizations
Measuring for Yourself
Measure to Plan
Measure to Operate
Measure to Optimize
Measure to Inspire and Aspire
Measuring for Stakeholders
Measure for Your CEO or Your Board
Measure for Finance
Measure for Strategic Peer Organizations
Measure for Tactical Peer Organizations
Sequencing Your Approach
Antipatterns
Summary
7. Participating in Mergers and Acquisitions
Complex Incentives
Developing a Shared Perspective
Business Strategy
Acquisition Thesis
Engineering Evaluation
Making an Integration Plan
Technology Integration Decisions
Team Integration Decisions
Leadership Integration Decisions
Dissent Now or Forever Hold Your Peace
Being Acquired
Summary
8. Developing Leadership Styles
Why Executives Need Several Leadership Styles
Leading with Policy
Examples
Mechanics
Leading from Consensus
Examples
Mechanics
Leading with Conviction
Examples
Mechanics
Isn’t This Micromanagement?
Development
Balancing Leadership Styles
Summary
9. Managing Your Priorities and Energy
“Company, Team, Self” Framework
Energy Management Is Positive-Sum
Eventual Quid Pro Quo
Mirrors of Misalignment
Orthogonal but Not in Opposition
Remain Flexible
Summary
10. Meetings for an Effective Engineering Organization
Why Have Meetings?
Six Essential Meetings
Weekly Engineering Leadership Meeting
Weekly Tech Spec Review and Incident Review
Monthlies with Engineering Managers and Staff Engineers
Monthly Engineering Q&A
What About Other Meetings?
Who Runs the Meetings?
Scaling Meetings
Summary
11. Internal Communications
Maintain the Drip
Test Before Broadcasting
Build the Packet
Keep It Short
Use Every Channel
Summary
12. Building Personal and Organizational Prestige
Brand Versus Prestige
Is Building Prestige Worthwhile for You?
Manufacture Prestige with Infrequent, High-Quality Content
Measuring Prestige Is a Minefield
Summary
13. Working with Your CEO, Peers, and Engineering
Are You Supported, Tolerated, or Resented?
Navigating the Implicit Power Dynamics
Bridging Narratives
Don’t Anchor to Previous Experience
Fostering an Alignment Habit
Focusing on a Small Number of Changes
Having Conflict Is Fine, Unresolved Conflict Is Not
Surviving Peer Panic
Summary
14. Gelling Your Engineering Leadership Team
Debugging and Establishing the Team
Operating Your Leadership Team
Expectations of Team Members
Competition Amongst Peers
Summary
15. Building Your Network
Leveraging Your Network
What’s the Cheat Code?
Building the Network
Working Together
Cold Outreach
Community Building
Writing and Speaking
Large Communities
What Doesn’t Work
Other Kinds of Networks
Founders
Venture Capitalists
Executive Recruiters
Summary
16. Onboarding Peer Executives
Why This Matters
Onboarding Executives Versus Onboarding Engineers
Sharing Your Mental Framework
Define Your Roles
Trust Comes with Time
How Much Progress Is Possible?
Summary
17. Inspected Trust
Limitations of Managing Through Trust
Trust Alone Isn’t a Management Technique
Why Inspected Trust Is Better
Inspection Tools
Incorporating Inspection in Your Organization
Summary
18. Calibrating Your Standards
The Peril of Misaligned Standards
Matching Your Organization’s Standards
Escalate Cautiously
Role Modeling for Your Peers
Adapting Your Standards
Summary
19. How to Run Engineering Processes
Typical Pattern Progression
Early Startup
Baseline
Specialized Engineering Roles
Company Embedded Roles
Business Unit Local
Patterns’ Pros and Cons
Early Startup
Baseline
Specialized Engineering Roles
Company Embedded Roles
Business Unit Local
Operating the Baseline Pattern
Dealing with Budgeting Realities
Navigating the Trend Cycle
Summary
20. Hiring
Establish a Hiring Process
Pursue Effective Rather Than Perfect
Monitoring Hiring Progress and Problems
Helping Close Key Candidates
Leveling Candidates
Determining Compensation Details
Managing Hiring Prioritization
Training Hiring Managers
Hiring Internally and Within Your Network
Increasing Diversity with Hiring
Building an Engineering Brand
Should You Introduce a Hiring Committee?
Remember That the System Exists to Support You
Summary
21. Engineering Onboarding
Real-world Examples
Onboarding Fundamentals
Roles
Executive sponsor
Program orchestrator
Team manager
Onboarding buddy
Curriculum
Who Can Attend Engineering Onboarding?
Why Onboarding Programs Fail
Integrating with Company Onboarding
When to Prioritize Onboarding
Summary
22. Performance and Compensation
Conflicting Goals
Performance and Promotions
Feedback Sources
Titles, Levels, and Leveling Rubrics
Promotions and Calibration
Demotions
Floor for Feedback
Compensation
How Often Should You Run Cycles?
Avoid Pursuing Perfection
Summary
23. Using Cultural Survey Data
Reading Results
Taking Action on the Results
When to Change the Questions
Starting and Frequency
Summary
24. Leaving the Job
Succession Planning Before a Transition
Deciding to Leave
Am I Changing Jobs Too Often?
Leave With or Without Your Next Role?
Telling the CEO
Negotiating the Exit Package
Establish the Communication Plan
Transition Out and Actually Leave
Revisiting the Decision
Summary
Closing
A. Additional Resources
Foundational Reading
Building Valuable Things
Leading Your Team
Operating as an Engineering Executive
Interviewing, Hiring, and Job Searching
Running Meetings
Running Distributed Offices and Teams
B. Interviewing Engineering Executives
Avoiding the Unicorn Search
How Interviewing Executives Goes Wrong
Structure for Evaluating Executives
Four Areas of Evaluation
Executive Skills
Role and Company-specific Skills
Engineering Functional Expertise
Historical Performance and Behavior
Summary
C. Reading a Profit & Loss Statement
What’s in a P&L Statement
Learning from a P&L
Digging into the Questions
This Is an Ongoing Activity
Finding S-1s and 10-Ks
Summary
D. Starting Engineering Hubs
Hub, Not Remote
Why Add an Engineering Hub
Mission
Executive Engagement
Predictability
Integration
Summary
E. Magnitudes of Exploration
Standardization
Exploration
Tension
An Order of Magnitude Improvement
Limit Work-in-Progress
Index