Essential Takeaways from Lenny’s Podcast Interview Episode: Exploring Effective Interview Questions

Gün Karagöz
3 min readDec 13, 2023

Well-known newsletter writer and podcast host Lenny Rachitsky recently shared an episode, “My favorite interview questions from 100+ guests”. These questions are highly valuable for anyone involved in the hiring process or seeking to enhance their understanding of the questions that product leaders employ to identify top talent.

Since I started embracing Atomic Habits, I’ve developed a habit of structuring my notes to make them more organized and easy to read. This has helped me digest the information more efficiently and also makes it easier to find my notes when I need to refer back to them. I’m building my library of notes from books, podcasts, and courses in Coda, and I recently published some documents publicly.

I have done the same for this episode: I wrote down interview questions and highlighted answers, as well as the information about the interviewees, covering various types and scenarios that job seekers may encounter or hiring managers can use during the interview process.

Here is a summary of the interview questions from 17 product leaders:

  1. Eeke De Miliano — Question on attributing success beyond luck, reflecting self-awareness.
  2. Geoff Charles — Question about the hardest challenge faced and how it was overcome.
  3. Shishir Mehrotra — Teleportation device scenario to test problem-solving and critical thinking.
  4. Yuhki Yamashita — Questions on controversial product decisions and storytelling ability.
  5. Katie Dill, Karri Saarinen, Camille Hearst — Shared questions on work they’re most proud of, revealing motivations and judgments.
  6. Jiaona Zhang — Behavioral questions to assess the handling of ambiguity.
  7. Noah Weiss — Question on learned “unfair secrets” to improve team velocity and energy.
  8. Ben Williams — Questions on personal growth and curiosity.
  9. Meltem Kuran Berkowitz — Question about how siblings or parents would describe them, assessing self-awareness.
  10. Paige Costello — Inquiry into handling situations when things go wrong.
  11. Nikhyl Singhal — Question on challenging conventional wisdom.
  12. Ayo Omojola — Reflecting on decisions that worked out differently than expected.
  13. Scott Belsky — Questions revealing limitations and views on luck.
  14. Lauryn Isford — Question on impactful delivery and defining impact.
  15. Paul Adams — Advice on reference calls, asking about potential future feedback.

Here are the steps I followed for creating my document.

“Tell me something you did that worked out, but not for the reason that you thought it would work” — Ayo Omojola

Initially, I crafted a ‘list of questions’ from the podcast, emphasizing key parts of the responses. The episode’s transcript, readily available, saved me the hassle of repeated listening for transcription. Next, I enriched the ‘people’ database with details like their current/former roles, Twitter profiles, and links to their full episodes, using Lenny’s Bot and some extra research. I then linked this data to the ‘question’ section for a cohesive overview. Finally, I introduced the ‘View a Random Question’ feature for dynamic content engagement.

A short demonstration of Lenny’s Favorite Interview Questions Document

That’s a wrap on the insights from Lenny’s podcast and my process behind the document creation in Coda. Feel free to explore and copy the complete document here. Happy reading, and may it aid you in your interviewing or job-seeking journey!

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Gün Karagöz

Experienced Product Enthusiast, Data Generalist, Automation Expert and No-Code Software Developer https://gk.gunkaragoz.net