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Will Larson (Carta, Stripe, Uber, Calm, Digg)07 January 2024

The engineering mindset

6Frameworks
14Insights

Episode overview

Will Larson explains how the post-zero-interest-rate environment has shifted engineering leadership from rapid hiring toward accountability, prioritization, and tighter organizational design. He presents systems thinking and written strategy as practical tools, while warning that models and measurements must remain subordinate to reality and action. The conversation also covers sustainable writing, aligning engineering and product incentives, evaluating developer productivity, creating useful company values, and lessons from Digg's troubled version-four rewrite.

Key ideas

  • Treat engineers as accountable peers so they can grow into genuinely senior leadership roles.
  • Systems thinking models stocks and flows, but a model must yield when it conflicts with reality and eventually lead to action.
  • Strategy already exists even when unwritten; documenting it makes inconsistent assumptions and decisions easier to diagnose and improve.
  • Strong engineering strategies often impose boring constraints that concentrate limited capacity on the company's most important problems.
  • Sustainable writing comes from following energizing questions, connecting writing to current work, publishing consistently, and optimizing for a long horizon.
  • Engineering managers and product managers collaborate better when they understand each other's incentives and share accountability for outcomes.
  • Developer-productivity metrics such as DORA are useful diagnostic and educational tools, but do not independently determine whether a team is effective.
  • Useful company values are honest, applicable to real decisions, and reversible; Digg's failed rewrite illustrates how severe operational failures can still create valuable career learning.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 12

  • Will LarsonMentionswill is currently CTO at Carta he's been a software engineering leader at stripe Uber and Comm

    today my guest is Will Larson one of the most requested guests I've had on this podcast

  • Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter

    super super excited to be here

  • Richard RumeltRecommendsRichard was a longtime professor at UCLA Anderson School of Management was on the faculty of Harvard Business School

    the Richard rumelt book I think good strategy bad strategy is probably the right starting point

  • Eben HewittCoinedmentioned

    there's a technology strategy patterns by Evan Hitt

  • Alex XuMentionsmentioned

    Alex zuu from bite by go both asked just this question of just how do you make time to write

  • Gergely OroszMentionsmy career started out as what you might consider a pretty typical software engineer career

    I asked a few people what to ask you and this came up a lot uh gge oros

  • Henry WardCoinedHenry or our CEO has a blog post about trifectas

    Henry or our CEO has a blog post about trifectas

  • Nicole ForsgrenMentionsNicole is the developer productivity expert having written the award-winning book accelerate

    we had Nicole on the podcast and she talked through Dora and all the Frameworks that she recommends

  • Kevin RoseMentionsa co-founder of a company we started he started dig back in the day

    what Kevin Rose or or the board or some combination there realized is that dig was losing

  • Rich SchumacherMentionsone of the other Engineers

    myself and and Rich Schumacher like one of the other Engineers we had to write like a caching system from scratch

  • Steve JobsMentionsSteve Jobs is just uh the bar he held for the company and for technical talent and for excellence was not uh wavering.

    Steve Jobs joke people like crazy and then they look back that was the best part moment in my career

  • George LakoffCoinedmentioned

    don't think of an elephant by George leoff it's a really interesting book about framing things and conversations

Resources · 49

  • The Engineering Executive's PrimerCoinedbook · Will Larson

    he's releasing his newest book the engineering Executives primer in February of next year

  • An Elegant PuzzleCoinedbook · Will Larson

    he's the author of two essential books for all Engineers An Elegant puzzle and staff engineer

  • CalmMentionssoftware · Calm.com, Inc.

    he's been a software engineering leader at stripe Uber and Comm

  • StripeMentionscompany · Patrick Collison and John Collison

    he's been a software engineering leader at stripe Uber and Comm

  • CartaMentionscompany

    will is currently CTO at Carta

  • Irrational ExuberanceCoinedwebsite · Will Larson

    he also publishes regularly on his blog at lane.com which is a must-read for every engineer and Eng leader

  • DiggMentionscompany

    an amazing story about his time at dig and so much more

  • DevExMentionsother

    DX is designed by the researchers behind Frameworks such as Dora space and devx

  • DXMentionssoftware · DX

    DX a platform for measuring and improving developer productivity

  • DORAMentionsother · Nicole Forsgren and collaborators

    DX is designed by the researchers behind Frameworks such as Dora space and devx

  • SPACEMentionsother · Nicole Forsgren and collaborators

    DX is designed by the researchers behind Frameworks such as Dora space and devx

  • OneSchemaMentionssoftware · Christina Gilbert

    one schema the embeddable CSV importer for SAS customers

  • UberMentionscompany · Uber

    when I was at Uber some days I would do like six like interviews back toback

  • Staff EngineerCoinedbook · Will Larson

    I wrote my my last book staff engineer about like what is the career path for senior Engineers

  • Silent SpringMentionsbook · Rachel Carson

    her work is also kind of referencing the work in Silent Spring by Rachel Carson

  • LinkedInMentionswebsite · LinkedIn

    the infinite potential candidates like wandering around LinkedIn uh posting about their deep thoughts

  • GreenhouseUsessoftware

    you can go to your your applicant tracking system like Greenhouse or or whatever and pull the the historicals

  • The Standard KitCoinedother · Eric Vogel

    one of the engineers Eric Vogal wrote the standard kit and that is our strategy of the tools we use

  • How Big Things Get DoneRecommendsbook · Bent Flyvbjerg and Dan Gardner

    another book with similar characteristics is uh how big things get done by I forget the the authors

  • Amazon Web ServicesMentionscompany · Amazon

    constrained by where AWS or Google cloud or Azure have built out

  • RubyUsessoftware · Yukihiro Matsumoto

    another good example at at stripe was this idea of we run a a ruby monolith

  • Google CloudMentionsproduct · Google

    constrained by where AWS or Google cloud or Azure have built out

  • Microsoft AzureMentionsproduct · Microsoft

    constrained by where AWS or Google cloud or Azure have built out

  • JavaUsessoftware · James Gosling

    there's more there's more Java in in the stripe of 2023 than there was in the stripe of 2016

  • Good Strategy/Bad StrategyRecommendsbook · Richard Rumelt

    the Richard rumelt book I think good strategy bad strategy is probably the right starting point

  • The CruxRecommendsbook · Richard Rumelt

    I think the Crux also also quite good but but maybe I would read that one second

  • The Value Flywheel EffectRecommendsbook · David Anderson, Mark McCann, and Michael O'Reilly

    there's the value flywheel effect by um Anderson mccon and O

  • The Phoenix ProjectRecommendsbook · Gene Kim, Kevin Behr, and George Spafford

    the Phoenix project by Kimber spafford um which is kind of a modern rewrite of the goal

  • Technology Strategy PatternsRecommendsbook · Eben Hewitt

    there's a technology strategy patterns by Evan Hitt

  • MediumMentionswebsite · Medium

    it's too late to join medium like you'll never make it there's too many medium writers

  • SubstackUseswebsite · Substack Inc.

    when I joined substack I thought it was too late

  • SlackMentionssoftware · Slack Technologies

    they're not demanding because you're responding to an urgent DM on slack

  • IBMMentionscompany

    it's like the old like no one gets fired for buying IBM

  • AccelerateRecommendsbook · Nicole Forsgren, Jez Humble, and Gene Kim

    one of the most influential books in the last decade um in kind of software engineering leadership and and kind of infrastructure is accelerate

  • FacebookMentionscompany · Meta

    the execs went to visit the Facebook campus they saw the values rig up on the wall

  • AmazonMentionscompany · Jeff Bezos

    users first great Amazon value right

  • NetflixMentionscompany · Netflix

    there's Netflix which is like we're a team like a sports team we're we're not a family

  • AirbnbMentionscompany · Brian Chesky, Joe Gebbia, and Nathan Blecharczyk

    I was there during airb be's period of coming up with values

  • RedditMentionswebsite · Steve Huffman, Alexis Ohanian, and Aaron Swartz

    even out computed by Reddit long term was kind of the the fear

  • PythonUsessoftware · Guido van Rossum

    related to the way that python initiates variables used as default parameters

  • TwitterMentionswebsite · Twitter

    dig did that before Facebook or Twitter really innovated kind of the ad format

  • Google SearchMentionssoftware · Google

    the vast and traffic for that was driven by Google search

  • Google ReaderMentionssoftware · Google

    Google Reader had has some kind of similar components to it

  • Don't Think of an Elephant!Recommendsbook · George Lakoff

    don't think of an elephant by George leoff it's a really interesting book about framing things and conversations

  • Top ChefRecommendstv show

    something I do still watch is Top Chef with my wife she's a Top Chef Super Fan

  • Hard to Work WithCoinedother · Will Larson

    maybe the piece I most proud of from from last year was like hard to work with

  • Lenny's PodcastCoinedpodcast · Lenny Rachitsky

    you can find all past episodes or learn more about the show at Lenny's podcast.com

  • Apple PodcastsMentionssoftware · Apple Inc.

    you can subscribe to the show on Apple podcast Spotify or your favorite podcast app

  • SpotifyMentionssoftware · Spotify

    you can subscribe to the show on Apple podcast Spotify or your favorite podcast app

Spot an error or want something removed? Request a correction or removal.

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 1

Myth Buster16:30

You Already Have a Strategy, It's Just Not Written Down

Will pushes back on the common complaint that a company or team has 'no strategy.' Product, engineering, and business always have a strategy, it's just often unwritten and applied inconsistently. The first rule of strategy is that writing it down is what lets you debug and improve it.

  • The absence of a filled-in template doesn't mean the absence of a strategy.
  • There's always a strategy, it's just sometimes bad and often unwritten.
  • Written strategy lets you diagnose whether a PM is bad, misunderstanding it, or correctly applying a strategy that's wrong for the problem.
  • Debugging a mediocre written strategy beats arguing over an invisible one.

there's always a product strategy sometimes it's bad but there's always one

Will Larson · 18:00

the the first rule of strategy is that if you write it down then you can like improve it right

Will Larson · 18:00
#strategy#product#engineering-strategy#leadership

Hot Take· 4

Hot Take06:30

Stop Coddling Engineers, Treat Them as Adults

Will argues the industry treats engineers like children, sheltering them from the important, hard problems, which is actually bad for their growth. In the previous era, obsessing over retention led managers to coddle engineers, which was bad for the engineers, the teams, and the org. He sees a healthier shift toward holding engineers accountable, which is exactly what lets you put them into genuinely senior roles.

  • Sheltering engineers from what's important stunts their growth as adults.
  • Retention-obsessed management led to coddling, which is bad for efficiency and for the engineers themselves.
  • You can only put engineers in senior roles if you're comfortable holding them accountable.
  • Accountability is how senior engineers finally get the responsibility they've wanted.

I think that we often treat Engineers a little bit like children instead of giving them like the responsibilities and ability to actually Thrive as…

Will Larson · 06:30

get to like give Engineers real hard problems and we get to we get to actually hold them accountable and that means we can put…

Will Larson · 08:00
#engineering-culture#career#accountability#leadership
Hot Take19:00

Good Strategy Is So Boring It's Hard to Talk About

Will's contrarian point is that the best engineering strategies are boring and constraining, like 'we only use the tools we have today.' Engineers hate these because they feel like a loss of control, but the power of a boring strategy is that it focuses everyone's energy on the problems the company actually values.

  • A great strategy for almost all companies is to just use the standard kit you already have.
  • Boring strategies frustrate engineers who want new languages, databases, or cloud providers.
  • The value is focus: energy goes to what the company cares about, not tooling sprawl.
  • Alignment can be painful up front but pays off over time.

a really good strategy for almost all companies is like we just use the standard kit we already have today

Will Larson · 19:30
#strategy#engineering-strategy#constraints#focus
Hot Take32:30

The Biggest Risk to Writers Is Quitting, Not Starting Late

Will rejects the 'it's too late to start' fear about Substack, podcasts, or Medium. The real risk isn't growing too slowly or missing the wave, it's quitting early from burnout. If you keep writing good stuff, you build an audience over time and can carry it across platforms, treating content as an infinite game rather than a competition.

  • Everyone converges on the same hot topic (crypto, then AI), making it hard to say anything novel.
  • The biggest risk is burning out and quitting, not starting too late or growing slowly.
  • Keep writing good work and the audience compounds and travels with you across platforms.
  • It's an infinite game: other creators aren't competition, there's no cap on good thinkers.

the biggest risk to content creation of any sort is quitting soon because you get burned out

Will Larson · 32:30

if you just like keep writing good stuff you'll build an audience over time and you can take that audience from platform to platform

Will Larson · 33:00
#writing#content-creation#audience#longevity
Hot Take44:00

Give the EM and PM the Same Performance Rating

To fix misaligned incentives between engineering managers and product managers, Will forces the idea that an EM/PM pair is a pair and generally gets the same performance rating, calibrated together in the same meeting. Carta extends this to 'trifectas' that include business leadership, so everyone is graded on solving the entire set of constraints, not just their own function.

  • EM/PM pairs generally get the same rating, with exceptions only for clear individual non-performance.
  • The two are discussed and calibrated in the same meeting.
  • Carta's CEO wrote about 'trifectas' extending shared grading to business leadership.
  • Everyone is graded on solving for the entire set of constraints, not just their functional ones.

empm pairs are Pairs and they generally have the same performance rating

Will Larson · 44:00

you all get graded the same score based on your ability to um evaluate and solve for the entire set of constraints not just your…

Will Larson · 45:00
#management#incentives#product#performance-reviews

Explainer· 3

Explainer04:30

How the Market Shift Rewired What Great Eng Leaders Do

Will describes how the move from the zero-interest-rate era to today changed the engineering job. In the boom, a top engineering director could excel just by hiring well; now that hiring has collapsed to a couple of interviews a month, that same person can look like a low performer unless they lead the team, get into the details, and get right-sizing decisions correct. Teams now get cut, consolidated, and disappeared, which the industry avoided for a decade.

  • During the last decade, managers spent half their time or more hiring; now it can be two interviews a month or zero.
  • A director who was a top performer purely for hiring well can now be perceived as a low performer.
  • New critical competencies: leading the team, getting deeper into the details, and correct team sizing/allocation.
  • Teams disappearing, getting cut, and being consolidated is now a core part of the job.

teams are actually disappearing teams are getting cut down teams are getting Consolidated

Will Larson · 06:00
#engineering-leadership#layoffs#hiring#management
Explainer48:30

How to Actually Measure Engineering Productivity

Will explains that funding-based benchmarking gives a defensible answer that calms your board but doesn't help you run the org. The real signal comes from talking to engineers, who know if their teams are effective, and from showing a roadmap of meaningful things shipped in the last six months. DORA/Accelerate metrics are excellent for diagnosis but shouldn't be used to judge whether a team is good, and refusing to measure anything just cedes ground to non-experts.

  • Funding-based benchmarks are mechanical and mainly reduce board anger, not improve the org.
  • Engineers themselves will tell you if their teams are effective and often why not.
  • Showing a roadmap of meaty, high-impact work earns you space; an empty list rightly raises concern.
  • DORA metrics (from Accelerate) are diagnosis tools, not verdicts; a slow deploy tells you where to invest, not that you're a bad company.
  • Measuring something imperfect and educating people on its limits beats measuring nothing.

if you're a good leader and you talk to the engineers they will tell you like the engineers know if their teams are effective or…

Will Larson · 50:00

metrics are about educating the people consuming the metrics about the reality of the rich data underneath

Will Larson · 54:30
#engineering-productivity#metrics#dora#measurement
Explainer56:00

Good Company Values Are Honest, Applicable, and Reversible

Will lays out three tests for a useful value. It must be honest (you actually do what you claim), applicable (you can use it to make a real decision, like Stripe's 'optimize globally' vs Uber's implicit 'do what's good for your team'), and reversible (a sane company could hold the opposite). Values that fail reversibility, like 'we build good software' or 'Integrity,' are just identity values that feel good but can't guide any decision.

  • Copying another company's values (e.g. writing Facebook's on your own walls) doesn't work.
  • Honest: your decisions must match the value, or it undermines trust.
  • Applicable: Stripe's 'optimize globally' vs Uber's implicit 'optimize for your team' both guide real choices.
  • Reversible: if no sane company would hold the opposite (e.g. Integrity), it's a useless identity value.
  • Cut values down to about four that people can remember, and only keep ones that some group doesn't fit.

these are the three that I found really useful for any value like is it honest is it a applicable and can you reverse it

Will Larson · 1:00:00

Integrity like everyone has that nobody wouldn't want Integrity

Will Larson · 1:01:30
#company-values#culture#leadership#decision-making

Story· 3

Story09:00

The Systems-Thinking Trap: Measuring Forever, Never Fixing

Will tells the story of Stripe's incident management work, where the team got so deep into analyzing incidents that they lost track of whether anything was actually improving. He admits he was the one caught in the model, prioritizing measurement over improvement. His broader lesson: when your model conflicts with reality, reality is never the thing that's wrong.

  • At Stripe, incident analysis became so absorbing the team optimized for measurement, not improvement.
  • The mistake was his own, not the team's, showing how seductive a clean model is.
  • "Measure twice, cut once" doesn't mean measure infinitely and never cut.
  • When model and reality conflict, the model is wrong, and that gap is where the real learning is.

we weren't actually prioritizing improvements we were just prioritizing measurement

Will Larson · 10:00

reality is never wrong reality is always right your model is always wrong if it's in conflict with with reality

Will Larson · 10:30
#systems-thinking#incident-management#stripe#decision-making
Story22:00

Uber's No-Cloud Rule and Stripe's Ruby Monolith

Will gives two concrete strategy examples. Uber's 2014-era 'no cloud, own data centers' policy was annoying and forced them to reinvent everything, but it let them spin up in China in three months and move in and out of geopolitical constraints that cloud-dependent companies couldn't. Stripe's 'we run a Ruby monolith' policy focused engineers on user features instead of multi-language tooling. In both, lots of engineers hated the constraint, but that's not the point.

  • Uber ran its own data centers and could stand up in China in ~3 months (even craning racks in through the roof).
  • Cloud-dependent competitors are constrained by where AWS/Google/Azure have built out.
  • Stripe's Ruby monolith kept engineers building features rather than supporting many languages.
  • The goal of good strategy is to direct limited capacity at the problems you care about, not to appease everyone.

at Uber we only used our own data centers we didn't use the cloud

Will Larson · 22:00

the goal of good strategy is not to um appease everyone the goal of good strategy is to dictate how we invest The Limited capacities…

Will Larson · 24:00
#strategy#uber#stripe#infrastructure
Story1:02:00

The Digg v4 Rewrite That Went to Zero

Will's failure story is Digg's v4 complete rewrite, a decision made to add social functionality that he says never works out for anyone. On launch day there was champagne and sushi, but the site kept crashing; it took a month to get fully functional, with servers needing a restart every 12 hours until he finally traced the core bug to how Python initializes default parameter variables. The team pulled off a heroic recovery, but Digg still went to zero and sold for parts.

  • A full rewrite to add social features was a decision made ~2.5 years before he joined; it 'never works out for anyone.'
  • Launch day had caterers, champagne, and sushi, but the site wouldn't stay up.
  • Servers had to be restarted every 12 hours even with a hastily written caching system.
  • The core bug was Python's handling of variables used as default parameters, written by someone new to Python.
  • Despite a heroic recovery, layoffs cut the team from ~100 to ~30 and Digg eventually sold for parts.

a complete rewrite in order to get there this is a decision that never works out for anyone

Will Larson · 1:03:30

related to the way that python initiates variables used as default parameters

Will Larson · 1:06:00
#failure#digg#rewrites#engineering-war-story

Tool· 1

Tool25:00

Will Larson's Reading List for Getting Better at Strategy

Asked how to actually get better at strategy, Will recommends a specific stack of books. Good Strategy Bad Strategy by Richard Rumelt is the starting point, Thinking in Systems by Donella Meadows for modeling reality, plus engineering-specific titles. He notes the canonical engineering-strategy book still feels missing, which is part of why he's writing one.

  • Start with Good Strategy Bad Strategy (Rumelt); read The Crux second.
  • Thinking in Systems (Meadows) helps you model reality and improve your diagnosis.
  • Engineering-specific: Technology Strategy Patterns, The Value Flywheel Effect, The Phoenix Project.
  • Will feels the canonical engineering-strategy book still doesn't exist.

the Richard rumelt book I think good strategy bad strategy is probably the right starting point

Will Larson · 25:30
#books#strategy#recommendations#engineering-strategy

Takeaway· 2

Takeaway27:30

Write What Energizes You, Then Just Publish It

Will's core writing philosophy is that you can write far more if you write what you actually want to write, not for money, deadlines, or an audience. He abandoned an infrastructure book that just wasn't coming together, because forcing unenergizing writing takes you negative. His publishing rule: he ships almost everything he writes, and if he can tell up front he won't publish something, he doesn't even start it.

  • Writing on someone else's topic and deadline is draining; owning the schedule is where the energy is.
  • He gave up an infrastructure engineering book when it wouldn't come together.
  • He publishes almost everything he writes, accepting that some of it isn't that good.
  • A quick internal check ('can I write and publish this?') stops him from starting doomed drafts.

you can write a lot more if you write what you want to write

Will Larson · 27:30

I publish pretty much everything I write

Will Larson · 39:00
#writing#content-creation#energy-management#career
Takeaway1:14:30

Why High-Standards People Get Labeled 'Hard to Work With'

Will's proudest recent piece, 'Hard to Work With,' names a trap he lived through early in his career: talented people who hold peers to a high standard get labeled combative or difficult, even though they think they're just being rigorous. Companies say they want high standards, but when you actually enforce them, people can turn on you. He hopes more people read it because many of the most talented workers never crack this idea.

  • Very talented people who hold peers to a high standard often get seen as combative or hard to work with.
  • It comes from his own early career, where trying to hold people accountable made colleagues say he sucked to work with.
  • Companies claim high standards but don't always actually want them enforced.
  • Many talented, caring people go their whole careers without resolving this and are despised precisely because they care so much.

I see a lot of people who are incredibly talented but they try to hold their peers to a high standard and then they're viewed…

Will Larson · 1:14:30
#career#high-standards#collaboration#writing