Will Larson

CTO at @imprintpayments. Wrote some books.

[Will Larson @Lethain]

A lot of folks want a map to Staff Engineer, and just as many Staff Engineers want to better understand their role. Towards that end, I'm working on a small project to collect folks' stories of reaching and operating as staff-plus engineers

https://t.co/CYUB736RJJ

[Will Larson @Lethain]

@timur_found @Pragmatic_Eng Might have been an Inktomi, aka Yahoo Search, special. As best I can tell Inktomi ran a prolonged insurgency against Yahoo control right until Microsoft/Yahoo Search Alliance (was that the name? Something like that) effectively ended that chapter

[Will Larson @Lethain]

@cjc @linear @GergelyOrosz @Pragmatic_Eng 😭

[Gergely Orosz @GergelyOrosz]

What’s changed in “the unwritten rules” of engineering management since the 2010s, why are hands-on managers “back”, and what has it done to the engineer-to-CTO career path? With Will Larson (@Lethain). 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
51:08 ZIRP’s impact on tech
57:21 Career ladders
1:01:03 Eng 1 vs Eng 2
1:06:58 How software engineering roles are changing
1:16:25 Revised rules of engineering leadership
1:21:57 The risks of becoming a bureaucrat as an EM
1:25:57 How to become a CTO?
1:31:33 Middle management vs. line management
1:41:36 Will’s writing
1:52:13 Book recommendations

Brought to you by:

• @turbopuffer – vector and full-text search built on object storage: fast, 10x cheaper, and extremely scalable. https://t.co/h4kBELKz20

• @EntireHQ – Git hosting, rebuilt for the agentic era. Entire hosts your code in-region, and is up to 89x faster than any other competitor. https://t.co/7yHVse7fpS

• What if you only needed a single test to harden your system? Get a free introduction to property-based testing: through a live, online webinar hosted by Hillel Wayne, author of Logic for Programmers and Developer Educator at @AntithesisHQ. RSVP here: https://t.co/QmpE5wHubY

Two sage observations from Will on how engineering management changed:

1. ZIRP shaped engineering management practices in the 2010s, Will believes. As he put it:

“Back then, your ability to hire and close and retain became the differentiator between successful companies. The less successful ones simply couldn’t retain great people.

[This dynamic on hiring and retaining] pulled leverage back into the engineer’s hands and created a very different environment. So, companies were pitching themselves as a more relaxed environment, more focused on you, and offering more career development. And I think in ways that I think were often kind of self-defeating.”

2. Blunt message for middle managers: retire or re-skill.

Will left a team of 250 at Carta to head up 25 tech people at Imprint. He purposely took a “step back” in his leadership career because he believes things are changing so radically that the engineering leadership profession that we know will not exist in three years.

Amid all this, Will says that line management can be a lot more engaging for executives these days because the tools for line management and the tools for writing software are really good. Plus, the tech industry has always been volatile: during the 2010s most of us simply forgot about this!

[Imprint @ImprintPayments]

What does it take to lead an engineering team today? Our CTO @Lethain joins @GergelyOrosz to dive into what’s changing and what it means for how teams build. Listen below 🎧

[Will Larson @Lethain]

Love getting to chat with Gergely! Ty @GergelyOrosz 🙏

[Gergely Orosz @GergelyOrosz]

What’s changed in “the unwritten rules” of engineering management since the 2010s, why are hands-on managers “back”, and what has it done to the engineer-to-CTO career path? With Will Larson (@Lethain). 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
51:08 ZIRP’s impact on tech
57:21 Career ladders
1:01:03 Eng 1 vs Eng 2
1:06:58 How software engineering roles are changing
1:16:25 Revised rules of engineering leadership
1:21:57 The risks of becoming a bureaucrat as an EM
1:25:57 How to become a CTO?
1:31:33 Middle management vs. line management
1:41:36 Will’s writing
1:52:13 Book recommendations

Brought to you by:

• @turbopuffer – vector and full-text search built on object storage: fast, 10x cheaper, and extremely scalable. https://t.co/h4kBELKz20

• @EntireHQ – Git hosting, rebuilt for the agentic era. Entire hosts your code in-region, and is up to 89x faster than any other competitor. https://t.co/7yHVse7fpS

• What if you only needed a single test to harden your system? Get a free introduction to property-based testing: through a live, online webinar hosted by Hillel Wayne, author of Logic for Programmers and Developer Educator at @AntithesisHQ. RSVP here: https://t.co/QmpE5wHubY

Two sage observations from Will on how engineering management changed:

1. ZIRP shaped engineering management practices in the 2010s, Will believes. As he put it:

“Back then, your ability to hire and close and retain became the differentiator between successful companies. The less successful ones simply couldn’t retain great people.

[This dynamic on hiring and retaining] pulled leverage back into the engineer’s hands and created a very different environment. So, companies were pitching themselves as a more relaxed environment, more focused on you, and offering more career development. And I think in ways that I think were often kind of self-defeating.”

2. Blunt message for middle managers: retire or re-skill.

Will left a team of 250 at Carta to head up 25 tech people at Imprint. He purposely took a “step back” in his leadership career because he believes things are changing so radically that the engineering leadership profession that we know will not exist in three years.

Amid all this, Will says that line management can be a lot more engaging for executives these days because the tools for line management and the tools for writing software are really good. Plus, the tech industry has always been volatile: during the 2010s most of us simply forgot about this!

[Will Larson @Lethain]

@GergelyOrosz Ty for having me!!

[Gergely Orosz @GergelyOrosz]

Podcast with @Lethain coming soon. Will has SO GOOD takes on eng leadership... because he is on the ground floor, and it's all first-hand.

Btw he left Carta (leading a team of ~250) to join a smaller team (~25 at Imprint originally) to "re-learn" what eng leadership means w AI

[lauren @poteto]

Part 2 is here! Let's learn the art of supervising someone smarter than you. https://t.co/UeV4pJ4NFx

[Will Larson @Lethain]

If we know each other, great! If we don't, also great! There are a few different roles underneath this one JD: https://t.co/tKUpZt6boY

[Will Larson @Lethain]

I'm hiring several key, hands-on engineering managers at @ImprintPayments. We'll work closely together. We'll build a product that a surprisingly large number of folks use as their top-of-wallet credit card. We'll use agents to rethink how software teams work. ✉️will@<handle>.com

[Will Larson @Lethain]

@groby @sgondala2 I think the signal i’d focus on for these is mostly whether they are thinking about the problems, not whether the answers are particularly “good”. Also agree with your point, profile of managers varies a lot, don’t think all would shine on this particular dimension

[Will Larson @Lethain]

How are folks evaluating Eng managers for AI abilities these days? Eg not ai engineer manager just any Eng manager. We’re doing some programming with AI, but doesn’t feel perfect…

[Will Larson @Lethain]

@Joseph_myke I think it’s systems thinking wrt how agents are changing workflows plus willingness to touch those workflows to really understand as a participant and not an armchair architect

[Will Larson @Lethain]

@rowlandekemezie The expectations are definitely shifting in my experience. A very odd moment in industry!

[Will Larson @Lethain]

@sagivo those are good questions try!

[Will Larson @Lethain]

@sgondala2 These are great ty!

[Sashank Gondala @sgondala2]

understand how they think about engineering in an ai-first world

- does code quality even matter anymore?
- what will codebases look like in an ai-first world?
- how much of review can be automated?
- what's the opinion on ai review + merge without human approval
- what are the biggest bottlenecks when building with ai? how are they solving them?
- how should hiring evolve? what about team structure
- what does seniority even mean going forward?
- how should credits be allocated across team?

i'm interested in whether they've spent time thinking about these things and not just answers

[Sagiv Ofek @sagivo]

@Lethain We stopped trying to evaluate the AI skill directly. Now we ask managers to walk us through the last thing they shipped with AI — what they delegated, what they checked by hand, and what broke. Tells you everything in about five minutes.

[Will Larson @Lethain]

@ich_code Yup, different tool chains

[Will Larson @Lethain]

Wrote up how we're trying to reduce PR review friction with concept of "small-change" as PRs/eng/week has increased 10x on some teams. (Aside: incidents down 42% HoH, critical incidents down 78%! Velocity vs quality never been a falser dichotomy.)

https://t.co/fxiU56rsF3

[Will Larson @Lethain]

@tweeshan Yes, it’s almost exclusively LLM assessment. All the deterministic evaluation is done in the small-change check by cicd before passing the check