The engineering mindset | Will Larson (Carta, Stripe, Uber, Calm, Digg)

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Will Larson is Chief Technology Officer at Carta. Prior to joining Carta, he was the CTO at Calm and held engineering leadership roles at Stripe, Uber, and Digg. He is the author of two foundational engineering career books, An Elegant Puzzle and Staff Engineer, and The Engineering Executive’s Primer, which will be released in February. In our conversation, we discuss:

• Systems thinking: what it is and how to apply it

• Advice for product managers on fostering productive relationships with engineering managers

• Why companies should treat engineers like adults

• How to best measure developer productivity

• Writing and its impact on his career

• How to balance writing with a demanding job

• How to develop your company values

Some takeaways:

1. Foster productive relationships between product managers and engineers by understanding each other’s incentives and needs. Promote open communication and collaboration to bridge the gap between different roles within the organization.

2. The first rule of strategy is to write it down. Until it’s written down, it’s hard to measure decisions against, and it’s easy to avoid useful discussions about what needs to be improved.

3. Utilize writing as a powerful tool for personal and professional growth. Focus on topics that genuinely excite you in order to avoid burnout.

4. No metric is perfect, and that’s okay. Questions about the validity of metrics are an opportunity to educate people on the nuances of what’s being measured. There is much less nuance in the alternative approach: measuring nothing at all.

5. To develop your company values, make sure they are (1) honest, (2) applicable, and (3) reversible. Avoid generic or identity values (like “we build good software”) that lack differentiation and fail to provide useful guidance for employees.

Listen now on Apple, Spotify, Overcast, and YouTube.

Find the full transcript at: https://www.lennyspodcast.com/the-engineering-mindset-will-larson-carta-stripe-uber-calm-digg/

Where to find Will Larson:

• X: https://twitter.com/Lethain

• LinkedIn: https://www.linkedin.com/in/will-larson-a44b543/

• Website: https://lethain.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Will’s background

(04:12) Changes in the field of engineering

(06:27) We need to stop treating engineers like children

(08:32) Systems thinking

(13:23) Implementing systems thinking in hiring

(16:32) Engineering strategy

(20:21) Examples of engineering strategies

(25:08) How to get good at strategy

(26:48) The importance of writing about things that excite you

(32:40) The biggest risk to content creation is quitting too soon

(35:24) How to make time for writing

(37:41) Tips for aspiring writers

(41:18) Building productive relationships between product managers and engineers

(43:45) Giving the same performance rating to EMs and PMs

(48:24) Measuring engineering productivity

(55:53) Defining company values

(01:02:10) Failure corner: the Digg rewrite

(01:11:05) Will’s upcoming book, The Engineering Executive’s Primer

(01:12:04) Lightning round

Referenced:

• The end of the “free money” era: https://www.theguardian.com/technology/2023/apr/11/techscape-zirp-tech-boom

• Work on what matters: https://lethain.com/work-on-what-matters/

• Sheryl Sandberg to Harvard Biz Grads: “Find a Rocket Ship”: https://www.forbes.com/sites/kashmirhill/2012/05/24/sheryl-sandberg-to-harvard-biz-grads-find-a-rocket-ship/?sh=708c9a93b37a

• What Is Systems Thinking?: https://www.snhu.edu/about-us/newsroom/business/what-is-systems-thinking

• Introduction to systems thinking: https://lethain.com/systems-thinking/

• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557

• Silent Spring: https://www.amazon.com/Silent-Spring-Rachel-Carson/dp/0618249060

• Writing an engineering strategy: https://lethain.com/eng-strategies/

• Carta: https://carta.com/

• Eric Vogl on LinkedIn: https://www.linkedin.com/in/ericvogl/

• Good Strategy/Bad Strategy: The difference and why it matters: https://www.amazon.com/Good-Strategy-Bad-difference-matters/dp/1781256179

• The Crux: How Leaders Become Strategists: https://www.amazon.com/Crux-How-Leaders-Become-Strategists/dp/1541701240/

• How Big Things Get Done: The Surprising Factors That Determine the Fate of Every Project, from Home Renovations to Space Exploration and Everything in Between: https://www.amazon.com/How-Big-Things-Get-Done/dp/0593239512/

• Technology Strategy Patterns: Architecture as Strategy: https://www.amazon.com/Technology-Strategy-Patterns-Architecture/dp/1492040878/

• The Value Flywheel Effect: Power the Future and Accelerate Your Organization to the Modern Cloud: https://www.amazon.com/Value-Flywheel-Effect-Accelerate-Organization/dp/1950508579

• The Phoenix Project: A Novel about IT, DevOps, and Helping Your Business Win: https://www.amazon.com/Phoenix-Project-DevOps-Helping-Business/dp/1942788290

• The Engineering Executive’s Primer: Impactful Technical Leadership: https://www.amazon.com/Engineering-Executives-Primer-Impactful-Leadership/dp/1098149483

• An Elegant Puzzle: Systems of Engineering Management: https://press.stripe.com/an-elegant-puzzle

• Staff Engineer: Leadership beyond the management track: https://www.amazon.com/Staff-Engineer-Leadership-beyond-management-ebook/dp/B08RMSHYGG

• Gergely Orosz’s newsletter: https://blog.pragmaticengineer.com/author/gergely/

• Leaving big tech to build the #1 technology newsletter | Gergely Orosz (The Pragmatic Engineer): https://www.lennyspodcast.com/videos/leaving-big-tech-to-build-the-1-technology-newsletter-gergely-orosz-the-pragmatic-engineer/

• The art of product management | Shreyas Doshi (Stripe, Twitter, Google, Yahoo): https://www.lennyspodcast.com/videos/the-art-of-product-management-shreyas-doshi-stripe-twitter-google-yahoo/

• Henry Ward on LinkedIn: https://www.linkedin.com/in/heward/

• Vrushali Paunikar on LinkedIn: https://www.linkedin.com/in/vrushali-paunikar/

• Accelerate: The Science of Lean Software and DevOps: Building and Scaling High Performing Technology Organizations: https://www.amazon.com/Accelerate-Software-Performing-Technology-Organizations/dp/1942788339

• How to measure and improve developer productivity | Nicole Forsgren (Microsoft Research, GitHub, Google): https://www.lennyspodcast.com/how-to-measure-and-improve-developer-productivity-nicole-forsgren-microsoft-research-github-goo/

• DORA: https://dora.dev/

• Setting engineering org values: https://lethain.com/setting-engineering-org-values/

• Digg: https://digg.com/

• Kevin Rose on LinkedIn: https://www.linkedin.com/in/kevinrose/

• Digg’s v4 launch: an optimism born of necessity: https://lethain.com/digg-v4/

• Dash Gopinath on LinkedIn: https://www.linkedin.com/in/dashgopinath/

• Rich Schumacher on LinkedIn: https://www.linkedin.com/in/richschumacher/

• The ALL NEW Don’t Think of an Elephant!: Know Your Values and Frame the Debate: https://www.amazon.com/ALL-NEW-Dont-Think-Elephant-ebook/dp/B00NP9LHFA

• Top Chef on Peacock: https://www.peacocktv.com/watch-online/tv/top-chef/5172289448907967112

• Hard to work with: https://lethain.com/hard-to-work-with/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.