The Engineering Executive's Primer: Impactful Technical Leadership

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
		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
About the Author