How to say something uncomfortable

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Claire Hughes Johnson is the former COO at Stripe, which she helped scale from a small startup to the legendary company it is today. She also spent close to 10 years at Google, where she filled several executive roles, including VP of Global Online Sales and Director of Sales and Ops for Gmail, YouTube, Google Apps, and AdWords. Claire shares invaluable insights from her upcoming book, Scaling People, on how to successfully build and scale organizations. We talk about the importance of building self-awareness, and Claire gives tons of tactical advice on how to say things that are hard to say, as well as how to improve your internal communications, and so much more.

Find the full transcript at: https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics

Where to find Claire Hughes Johnson:

• Twitter: https://twitter.com/chughesjohnson

• LinkedIn: https://www.linkedin.com/in/claire-hughes-johnson-7058/

Where to find Lenny:

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

• Twitter: https://twitter.com/lennysan

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

Referenced:

• Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212

• John Collison on LinkedIn: https://www.linkedin.com/in/johnbcollison/

• Patrick Collison on LinkedIn: https://www.linkedin.com/in/patrickcollison/

• Discord: https://discord.com/

• Toast: https://pos.toasttab.com/

• High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100

• Myers-Briggs personality types: https://www.myersbriggs.org/my-mbti-personality-type/mbti-basics/

• Enneagram types: https://www.enneagraminstitute.com/type-descriptions

• Disc assessment: https://www.discprofile.com/what-is-disc

• Conscious Business: How to Build Value through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020/

• Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/

• Eeke de Milliano on Lenny’s Podcast: https://www.lennyspodcast.com/how-to-foster-innovation-and-big-thinking-eeke-de-milliano-retool-stripe/

• Running an effective meeting: https://www.youtube.com/watch?v=GIiaFW874q8

• Gokul’s S.P.A.D.E. framework: https://coda.io/@gokulrajaram/gokuls-spade-toolkit

In this episode, we cover:

(00:00) Claire’s background

(04:47) How writing Scaling People helped Claire crystallize learnings

(07:58) How she got started writing her book

(11:11) Advice that changed the way she operates

(15:18) The lack of job titles at Stripe

(19:01) Scaling your organizational structure

(23:46) What founders need to think about in the early days

(26:38) Personal operating principles

(29:04) How to crystallize your own values to gain self-awareness

(34:29) Advice for saying uncomfortable things

(37:12) Being an explorer, not a lecturer

(43:57) Come back to the operating system

(47:17) Organizational structure using Claire’s house metaphor

(50:50) Why some chaos is normal

(52:45) Founding documents you need

(58:30) The components of a company’s operating system 

(1:01:31) Finding the right cadence

(1:04:48) COOs and which types of businesses need them

(1:11:30) Advice on scaling quickly

(1:13:56) The importance of internal communications

(1:16:03) Running effective meetings

(1:17:17) Advice for aligning and making decisions as a manager

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

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