A masterclass in engineering leadership from Carta, Stripe, Uber, and Calm | Will Larson (CTO at Carta)

Will Larson is the CTO at Carta, an ownership and equity management platform that raised at a $7.4b valuation in 2021. Prior to joining Carta, Will was CTO at Calm, founded Stripe's Foundation Engineering org, and led Uber’s Platform Engineering people and strategy. Will also writes extensively about engineering leadership, and has authored two books in this area: Staff Engineer, and An Elegant Puzzle.

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In today’s episode we discuss:

• How to form an engineering strategy
• Common engineering management mistakes, and how to avoid them
• Advice for explaining, measuring, and optimizing engineering velocity
• Will’s nuanced approach to organizational policies
• Why it’s sometimes counterproductive to tell someone not to micromanage

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Referenced:

• Accelerate (book): https://www.amazon.com/Accelerate-Software-Performing-Technology-Organizations/dp/1942788339
• Calm: https://www.calm.com/
• Carta: https://www.carta.com/
• DORA: https://dora.dev/
• Good Strategy, Bad Strategy (book): https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239
• JavaScript: https://www.javascript.com/
• KAFKA: https://kafka.apache.org/
• Minto Pyramid (framework): https://untools.co/minto-pyramid
• Ruby on Rails: https://rubyonrails.org/
• SPACE (framework): https://queue.acm.org/detail.cfm
• Stripe: https://www.stripe.com/

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Where to find Brett Berson:

• Twitter/X: https://twitter.com/brettberson
• LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/

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Where to find Will Larson:

• Twitter/X: https://twitter.com/lethain
• LinkedIn: https://www.linkedin.com/in/will-larson-a44b543/
• Personal website/blog: https://lethain.com/
• An Elegant Puzzle (book): https://www.amazon.com/Elegant-Puzzle-Systems-Engineering-Management/dp/1732265186
• Staff Engineer (book): https://staffeng.com/book

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Where to find First Round Capital:

• Website: https://firstround.com/
• First Round Review: https://review.firstround.com/
• Twitter: https://twitter.com/firstround
• Youtube: https://www.youtube.com/@FirstRoundCapital
• This podcast on all platforms: https://review.firstround.com/podcast

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Timestamps:

(00:00) Introduction

(03:03) The nuances of taking lessons from old companies

(14:28) The value of writing down engineering principles

(17:03) How to structure a strategy document

(18:48) The 2 parts of any engineering strategy

(21:08) Advice for turning strategy into action

(23:44) Carta's unique "navigator" model

(24:50) The Hidden Variable Problem

(29:59) Explaining, measuring, and optimizing velocity

(35:28) Useful metrics for engineering orgs

(39:08) The balance between micromanagement and understanding details

(43:03) Management anti-patterns

(45:49) How to execute policies whilst managing their exceptions

(47:56) What an excellent engineering executive looks like

(53:53) How Will has evolved as an engineering executive

(56:56) How to communicate with executives

(63:18) Things that derail meetings

(66:10) How to approach presentation feedback

(67:30) A bad sign when working with direct reports

(69:13) Advice for growing as an early-career engineer

(71:11) Will's model for developing engineering teams

(74:33) Sources of inspiration for Will's views on engineering management