The Engineering Executive's Primer

The Engineering Executive's Primer

by Will Larson
Released February 2024
Publisher(s): O'Reilly Media, Inc.
ISBN: 9781098149482

Read it now on the O’Reilly learning platform with a 10-day free trial.

O’Reilly members get unlimited access to books, live events, courses curated by job role, and more from O’Reilly and nearly 200 top publishers.

Buy on Amazon Buy on ebooks.com
Start your free trial

Book description

As an engineering manager, you almost always have someone in your company to turn to for advice: a peer on another team, your manager, or even the head of engineering. But who do you turn to if you're the head of engineering? Engineering executives have a challenging learning curve, and many folks excitedly start their first executive role only to leave frustrated within the first 18 months.

In this book, author Will Larson shows you ways to obtain your first executive job and quickly ramp up to meet the challenges you may not have encountered in non-executive roles: measuring engineering for both engineers and the CEO, company-scoped headcount planning, communicating successfully across a growing organization, and figuring out what people actually mean when they keep asking for a "technology strategy."

This book explains how to:

  • Get an engineering executive job, negotiate the contract, and onboard at your new company
  • Run an engineering planning process and communicate effectively with the organization
  • Direct the core meetings necessary to operate an effective engineering organization
  • Hire, onboard, and run performance management
  • Manage yourself and remain effective through many challenges
  • Leave the job when the time is right

Will Larson was the chief technology officer at Calm and the author of An Elegant Puzzle and Staff Engineer. He's also a prolific writer on his blog, Irrational Exuberance.

Publisher resources

View/Submit Errata

Table of contents

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

Product information

  • Title: The Engineering Executive's Primer
  • Author(s): Will Larson
  • Release date: February 2024
  • Publisher(s): O'Reilly Media, Inc.
  • ISBN: 9781098149482