The Art of True Listening in Leadership

Shreyas Doshi is a former product leader at Stripe, Twitter, Google, and Yahoo. He’s now a full-time advisor and coach to founders and executives. Shreyas is known for his incredibly insightful writing on products, which has garnered him a passionate following in the PM and startup community. Last week, we sat down together at the very first Lenny and Friends Summit in San Francisco for a special live episode. We covered:

• Why product leaders often feel overwhelmed with work, and how to combat it

• The importance of developing good taste, and how to do it

• How to reduce frustration in your product leadership role

• The critical skill of truly listening as a leader

• Common pitfalls in annual planning and decision-making

• Lots of laughs

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To learn more from Shreyas, check out these courses:

• Improving Your Product Sense: https://bit.ly/product-sense

• Managing Your PM Career: https://bit.ly/pm-career-course

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Find the transcript at: https://www.lennysnewsletter.com/p/shreyas-doshi-live

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Where to find Shreyas Doshi:

• X: https://x.com/shreyas

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

• Threads: https://www.threads.net/@shreyas.threads

• Linktree: https://linktr.ee/shreyasdoshi

• YouTube: https://www.youtube.com/@ShreyasDoshiVideos

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Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Introduction

(05:35) Question one: Why am I so busy?

(10:08) Annual planning as an example

(16:48) Tactical tips for staying less busy

(25:20) Question two: Do I actually have good taste?

(38:09) Question three: Why does my job feel so frustrating?

(43:29) Question four: Am I really listening?

(44:35) Closing remarks

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Referenced:

• Shreyas Doshi on pre-mortems, the LNO framework, the three levels of product work, why most execution problems are strategy problems, and ROI vs. opportunity cost thinking: https://www.lennysnewsletter.com/p/episode-3-shreyas-doshi

• LNO framework: https://twitter.com/shreyas/status/1492345184171945984

• Time management techniques that actually work: https://www.lennysnewsletter.com/p/time-management-techniques-that-actually

• Part 2: Time management techniques that actually work: https://www.lennysnewsletter.com/p/part-2-time-management-techniques

• Eisenhower quote: https://www.brainyquote.com/quotes/dwight_d_eisenhower_164720

• Stripe Connect: https://stripe.com/connect

• Jeff Bezos explains one-way door decisions and two-way door decisions: https://www.youtube.com/watch?v=rxsdOQa_QkM

• Spotify Is America’s Most Loved Workplace: https://www.newsweek.com/2021/10/29/spotify-americas-most-loved-workplace-1639982.html

• Shreyas on “thinking is cheap”: https://www.linkedin.com/posts/shreyasdoshi_thinking-is-very-cheap-doing-is-very-expensive-activity-7225237421813116929-Qzi3/

• Good Product Strategy, Bad Product Strategy from Shreyas: https://x.com/shreyas/status/1244810075908128768

• Shreyas on annual planning and metrics:

https://x.com/shreyas/status/1302423854095036421

https://x.com/shreyas/status/1304628719374544896

• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang/

• Patrick Mahomes’s website: https://www.adidas.com/us/patrick_mahomes

• Virat Kohli: https://en.wikipedia.org/wiki/Virat_Kohli

• Reversible and Irreversible Decisions: https://fs.blog/reversible-irreversible-decisions/

• Fail fast: https://en.wikipedia.org/wiki/Fail_fast

• 3 levels of product work: https://twitter.com/shreyas/status/1370248637842812936

• Shakespeare quote: https://nosweatshakespeare.com/quotes/famous/to-thine-own-self-be-true/

• Rick Rubin: Legendary Music Producer | Lex Fridman Podcast #275: https://Dwww.youtube.com/watch?v=H_szemxPcTI

• Blake Burge on Rick Ruben: https://x.com/blakeaburge/status/1794470295828341222

• Rick Rubin on X: https://x.com/RickRubin

• Dee Hock on X: https://x.com/deewhock

• Dee Hock quote on listening: https://x.com/shreyas/status/1351279398423465984

• Peter Drucker: https://en.wikipedia.org/wiki/Peter_Drucker

• Peter Drucker quotes on listening: https://www.azquotes.com/author/4147-Peter_Drucker/tag/listening

• Lenny’s first podcast recording: https://www.youtube.com/watch?v=YP_QghPLG-8

• A Recipe to Become a Great Listener: https://www.youtube.com/watch?v=gUQJkiDy2Ko

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

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Lenny may be an investor in the companies discussed.

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