An Elegant Puzzle: Systems of Engineering Management

An Elegant Puzzle: Systems of Engineering Management

Author: Will Larson
Published: 2019
Genre: Technical Leadership, Engineering Management

Overview

Will Larson’s “An Elegant Puzzle” distills years of experience building and scaling engineering organizations at companies like Uber, Digg, and Stripe. While written for engineering managers, the book is invaluable for Staff+ engineers who need to understand organizational dynamics, influence without authority, and navigate complex technical decisions in growing companies.

Key Concepts

Team Sizing and Structure

• The Four States of Teams:

  • Falling Behind: More work than capacity, accumulating backlog
  • Treading Water: Critical work completed, but no time for technical debt
  • Repaying Debt: Can start paying down technical debt and improving systems
  • Innovating: Capacity for exploratory work and experimentation

• Team Sizing Formula: Teams of 6-8 engineers with a manager who supports 4-6 teams creates healthy organizational structure

• Solution: Add teams to falling behind areas, consolidate treading water teams to create capacity

Systems Thinking for Organizations

• Organizational Debt: Like technical debt, but for organizational structures and processes
• Fixed Cost vs Variable Cost: Certain organizational patterns have high fixed costs (platform teams) that only pay off at scale
• Succession Planning: Every role should have a clear succession plan; blocking others’ growth blocks your own

Technical Strategy and Vision

• Write the Strategy Doc First: Before building, write the strategy that explains why
• Good Strategy: Diagnosis of current state, guiding policies, and coherent actions
• Technical Vision: 2-3 year aspiration for your system with clear reasoning about trade-offs
• Architecture Decision Records (ADRs): Document not just what you decided, but why and what alternatives were considered

Migrations and Refactoring at Scale

• De-risk Migration: Run both old and new systems in parallel before cutting over
• Enable Deletion: The goal of migration isn’t new code, it’s deleting old code
• Measure Progress: Define clear metrics for migration completion and track weekly

Staff Engineer Implications

For Staff+ engineers, this book provides crucial insights:

• Understand Team Health: Recognize when teams are falling behind vs innovating - influences where to invest your time
• Think in Systems: Your technical decisions create organizational constraints
• Document Decisions: ADRs and strategy docs are force multipliers for Staff+ engineers
• Enable Others: Your job is increasingly about enabling teams to move faster

Quick Facts

• Organizations that grow >2x annually need fundamentally different systems each year
• Productivity follows an S-curve: slow ramp, rapid growth, then plateau
• 70% of engineer effectiveness comes from organizational factors, not individual skill
• Technical migrations take 3x longer than planned; factor this into estimates
• “Posting” a strategy doc without discussion yields 10% of the value of proper socialization

Practical Takeaways

1. Before Proposing Solutions: Diagnose the problem thoroughly. Half-understood problems lead to wrong solutions
2. Create Leverage: As a Staff engineer, multiply your impact through documentation, tooling, and enabling systems
3. Succession Over Heroism: Being irreplaceable is a bug, not a feature
4. Manage Energy, Not Time: Protect focus time for deep technical work; batch interrupts
5. Write It Down: Unwritten decisions are unmade decisions. Document for future you and future teammates

Relevant Chapters for Staff Engineers

• Chapter 2: Organizations - Understanding team sizing and structure
• Chapter 3: Tools - Systems thinking, migrations, metrics
• Chapter 4: Approaches - Vision, strategy, and organizational learning
• Chapter 5: Culture - Building engineering culture and career frameworks

Bottom Line

“An Elegant Puzzle” bridges the gap between pure technical work and organizational dynamics. For Staff+ engineers, it provides the language and frameworks to diagnose organizational problems, propose systemic solutions, and understand why some technical decisions succeed while others fail regardless of technical merit. The book’s systems-thinking approach helps senior ICs understand that solving technical problems at scale requires solving organizational problems.

Best for: Staff/Principal engineers who find themselves frustrated with organizational dynamics, want to amplify their impact beyond code, or are considering the transition to management.