The revised rules of engineering management with Will Larson

October 21, 2026

AI Summary

5 min read

Will Larson has spent a decade as an engineering executive at four different companies, written widely-read books on engineering leadership, and watched the industry flip from an era of zero-interest-rate abundance to one of efficiency and smaller teams. In this conversation, he traces how the habits formed in the 2010s—managers who never made technical decisions, engineers who expected interesting work, and organizations that optimized for headcount—are now being actively dismantled. The revised rules of engineering management, he argues, demand a return to technical depth, durable teams, and a willingness to solve the business's actual problems.

The ZIRP hangover: how a decade shaped bad habits

Larson points to the zero-interest-rate period (ZIRP) as the hidden force that shaped a generation of management practices. When capital was cheap and hiring was the primary constraint, managers were incentivized to be people-pleasers and headcount-fillers. "The hiring is the least interesting way to solve every problem," Larson says now, but in the 2010s, managers who couldn't make technical decisions had only two levers: process and people. This drove org bloat and a culture where engineers were shielded from business realities.

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What you'll learn

1 (00:00) **Introduction** - Will Larson discusses how engineering management has changed in the last few years.
2 (02:48) **Will's Early Interest in Computers** - Will shares how he got started with computers as a child.
3 (04:36) **College and Early Career** - Will describes his path into computer science and his first job.
4 (07:53) **Yahoo Experience** - Will recounts his time at Yahoo, including the company's unique internal tools.
5 (11:57) **Dig and the V4 Rewrite** - Will tells the story of the disastrous Dig v4 launch.
6 (25:06) **Path to Engineering Leadership at Uber** - Will explains how he moved into engineering leadership at Uber.
7 (32:06) **Stripe and Becoming a CTO** - Will describes his time at Stripe and his move to CTO roles.

+ Full timestamped outline available in the app

Show Notes

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What’s changed in “the unwritten rules” of engineering management since the 2010s, what drove the shift to today, and what has it done to the engineer-to-CTO career path? Today’s guest is one of the best people I know who can tackle these questions.

Will Larson is CTO of Imprint, was an engineering executive for 10+ years, and is the author of several popular books on engineering leadership, including ‘The Engineering Executive's Primer,’ ‘Staff Engineer, An Elegant Puzzle,’ and ‘Crafting Engineering Strategy.’ Previously, he was also CTO at Carta and Calm, and an engineering leader at Stripe and Uber.

In this episode, we explore how engineering leadership has evolved from management practices shaped in the long post-financial-crisis ZIRP era to the altered expectations of engineers and managers today.

Is middle management an increasingly precarious career path, and might managers need to reskill and return to hands-on technical work – or even consider retirement? Will makes the case, and we hear why the traditional path to engineering executive roles is changing, as well as why taking one step backward might sometimes be the best way forward.

We discuss Will's early career, and get his first-hand account of Digg's disastrous relaunch, his own path to CTO, and he tells us why career ladders still matter. We also explore how AI is changing engineering roles and bringing technical decision-making back to leadership.

Timestamps

00:00 Intro

08:20 Stories from Yahoo!

12:47 Digg’s v4 rewrite: the insider story

26:02 Will’s path to eng leadership

30:03 Uber, Stripe, Carta, and Calm

35:11 What does a CTO do?

38:09 Will’s role at Imprint

42:48 How engineering management has evolved