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Will Larson Reflects on Staff Engineer

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Dec 8, 2025

Guest

Will Larson

Will Larson, an engineering leader and author known for his works on staff roles and strategy, shares unique insights from his experience at top companies like Stripe and Uber. He dives into the pitfalls of productivity, explaining anti-patterns like 'snacking' and how outdated assumptions can hinder innovation. Will emphasizes the importance of sponsorship over mentorship and offers practical tips on structuring projects for quick learnings. He also discusses the value of building learning circles and the broader applicability of his insights beyond Silicon Valley.

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insights

INSIGHT

Authority Narrows With Seniority

Senior roles shrink the set of valid actions even as they grant more authority.
Staff engineers must learn which uses of authority are safe and effective inside leadership constraints.

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ADVICE

Balance Conviction With Alignment

Ignore optics when reality matters but still align upward with leadership.
Balance conviction about technical truth with pragmatic alignment to avoid being marginalized.

insights

INSIGHT

Watch For Outdated Assumptions

Many engineers chase problems that no longer matter because conditions changed.
Calibrate whether a concern is still a bottleneck before investing effort.

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Why Will Wrote Staff Engineer

01:45 • 3min

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Preening, Snacking, and Pseudo-Productivity

04:50 • 2min

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Conviction vs. Alignment for Senior Engineers

Chasing Ghosts and Outdated Assumptions

09:24 • 4min

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Transitioning Between Very Different Companies

13:30 • 2min

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Job Hopping: Benefits and Tradeoffs

15:28 • 3min

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When Staff Roles Don't Fit

18:39 • 4min

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Senior Roles Have Downsides Too

22:52 • 2min

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Sponsorship vs. Mentorship Importance

25:04 • 5min

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Create Your Own Network and Learning Circles

29:51 • 4min

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How Will Runs a Learning Circle

34:06 • 2min

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Developing Intuition by Asking Questions

36:35 • 2min

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Structuring Big Initiatives to Fail Fast

38:36 • 3min

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Evaluating Migrations and When to Pause

41:23 • 7min

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Design for Decoupling and Incremental Change

48:41 • 3min

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Book Relevance Beyond Silicon Valley

51:19 • 5min

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Collecting Stories to Shape the Role

56:26 • 3min

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Recommended Reading and New Book

• Mentioned in 2 episodes

Crafting Engineering Strategy

How Thoughtful Decisions Solve Complex Problems

Will Larson

Crafting Engineering Strategy is a practical guide for engineering leaders looking to develop and execute effective strategies. It covers key aspects of strategy development, such as assessing the current state, defining goals, and identifying strategic initiatives. The book provides frameworks and tools for analyzing the competitive landscape and aligning engineering efforts with business objectives. It emphasizes the importance of communication and collaboration in driving strategic initiatives. The book also offers guidance on how to measure and track the success of engineering strategies. Crafting Engineering Strategy is a valuable resource for engineering leaders seeking to improve their strategic thinking and execution capabilities.

#5176

• Mentioned in 8 episodes

An Elegant Puzzle

Systems of Engineering Management

Will Larson

An Elegant Puzzle is a comprehensive guide to engineering management, particularly in high-growth environments. The book, written by Will Larson, draws on his extensive experience at companies like Digg, Uber, and Stripe. It addresses specific challenges such as managing technical debt, handling migrations, and developing succession planning. Larson's approach emphasizes systems thinking, providing actionable templates and strategies for building healthy and productive engineering teams. The book is valuable not only for engineering managers but also for product managers and engineers working in similar environments.

#10234

• Mentioned in 4 episodes

Staff Engineer

Tanya Reilly

Will Larson

This book explores the role of a Staff Engineer, providing insights into leadership, career growth, and strategic thinking without following the management track. It includes interviews with experienced Staff Engineers and offers practical advice on achieving and succeeding in this role.

#102

• Mentioned in 146 episodes

Slow Productivity

The Lost Art of Accomplishment Without Burnout

Cal Newport

In this book, Cal Newport draws on the habits and mindsets of historical figures like Galileo, Isaac Newton, Jane Austen, and Georgia O’Keefe to propose a new approach to productivity. He argues against the modern culture of 'pseudo-productivity,' where busyness is mistaken for actual productivity. Instead, Newport advocates for 'slow productivity,' which involves doing fewer things, working at a natural pace, and obsessing over quality. The book combines cultural criticism with practical advice to help readers transform their work habits and achieve more sustainable and meaningful accomplishments.

#1540

• Mentioned in 22 episodes

A pattern language

Towns, Buildings, Construction

Christopher Alexander

This book, written by Christopher Alexander and his colleagues, introduces the concept of a 'pattern language' consisting of 253 patterns that address various design problems in architecture, urban planning, and community design. Each pattern describes a recurring problem and its solution, allowing readers to adapt these solutions to their specific needs and local conditions. The book is structured to help ordinary people, as well as professionals, design and improve their homes, streets, and communities. It has had significant influence on fields beyond architecture, including software engineering and urban planning.

#371

• Mentioned in 61 episodes

This book introduces readers to systems thinking, a critical skill for 21st-century life. It explains how to understand and interact with complex systems, highlighting the importance of internal system structures and feedback loops. The book is divided into sections on system structures and behavior, the relationship between systems and humans, and strategies for creating change within systems. It aims to help readers develop a deeper understanding of systems to address global issues such as climate change, poverty, and social inequalities.

In this special episode of Book Overflow, Carter and Nathan are joined by Will Larson, author of Staff Engineer!

The first ten listeners to tag Book Overflow on LinkedIn and share a link to this interview will receive a free copy of Will's new book, Crafting Engineering Strategy!

-- Want to talk with Carter or Nathan? Book a coaching session! --

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Carter

https://www.joinleland.com/coach/carter-m-1

Nathan

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or work with Nathan through his consulting practice, rojoroboto. Book Overflow Listeners get 10% off their first engagement https://rojoroboto.com/bookoverflow

-- Books Mentioned in this Episode --

Note: As an Amazon Associate, we earn from qualifying purchases.

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Staff Engineer by Will Larson

https://amzn.to/4p67dOUn (Paid Link)

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00:00 Intro

01:44 Interview with Will Larson

05:00 Anti-patterns - Snacking, Pining, and Chasing Ghosts

18:42 Navigating Senior Roles and Finding Sponsors

36:26 Developing Intuition and Running Migrations

48:47 Writing Staff Engineer - Stories and Archetypes

58:45 Book Recommendations and Closing

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Spotify: https://open.spotify.com/show/5kj6DLCEWR5nHShlSYJI5L

Apple Podcasts: https://podcasts.apple.com/us/podcast/book-overflow/id1745257325

X: https://x.com/bookoverflowpod

Carter on X: https://x.com/cartermorgan

Nathan's Weekly Reflections Newsletter: https://rojoroboto.com/newsletter

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Book Overflow is a podcast for software engineers, by software engineers dedicated to improving our craft by reading the best technical books in the world. Join Carter Morgan and Nathan Toups as they read and discuss a new technical book each week!

The full book schedule and links to every major podcast player can be found at https://www.bookoverflow.io

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