The Best Interview Questions from Lenny's Podcast (Compilation)

The Best Interview Questions from Lenny's Podcast (Compilation)

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The Best Interview Questions from Lenny’s Podcast (Compilation)

A compilation of 17 favourite interview questions drawn from the lightning rounds of over 100 Lenny’s Podcast guests. Intended as a reference for interviewers preparing for candidate reviews and candidates preparing for PM interviews. The episode features short clips from existing guests; it does not contain original interview content.

Key ideas

  • Eigenquestion: Shishir Mehrotra’s framework — the Eigenquestion is the one or two questions whose answers unlock the rest. His teleportation device exercise forces candidates to identify the Eigenquestions in a novel domain by restricting them to just two questions after open brainstorming; the constraint reveals whether someone can get to the heart of a problem.

  • Introspection and self-awareness as the common thread: Across many of the best interview questions — “to what do you attribute your success?”, “what’s the hardest thing you’ve done?”, “tell me something that worked but not for the reason you thought” — interviewers are testing whether the candidate has built an accurate mental model of themselves and their decision-making.

  • Reference check question: Paul Adams (Intercom) asks references “what feedback will I be giving this person in their first performance review?” The constraint that there is an answer prevents evasion and surfaces real developmental observations.

  • Breaking interview mode: Nikhyl Singhal (Facebook) asks “what’s something everyone takes for granted that you think is hogwash?” specifically to break candidates out of prepared-answer mode; authentic opinions cannot be pre-scripted.

  • Pride as a signal of taste and motivation: Three interviewers — Katie Dill (Stripe), Karri Saarinen (Linear), Camille Hearst (Spotify) — independently converged on “tell me about something you’re most proud of.” What someone is proud of reveals their values, taste, and what “good” means to them.

Guest contributions

GuestQuestion/theme
Eeke De Miliano (Retool)“To what do you attribute your success?” (can’t say luck)
Geoff Charles (Ramp)“What’s the hardest thing you’ve ever done?”
Shishir Mehrotra (Coda)Eigenquestion test — teleportation device; what two questions would you ask?
Yuhki Yamashita (Figma CPO)“Describe a time you were part of a controversial product decision.”
Katie Dill (Stripe)“Tell me what work you are most proud of?”
Karri Saarinen (Linear CEO)“What are you most proud of and why?”
Camille Hearst (Spotify)“Tell me about something you’re really proud of — take me through the process.”
Jiaona Zhang (Webflow)Behavioural: how do you navigate ambiguity?
Noah Weiss (Slack CPO)“What unfair secrets have you learned to improve a product team?”
Ben Williams (Snyk)“Fast forward three years — what’s different about you then?”
Meltem Kuran Berkowitz (Deel)“What would your siblings say about you?”
Paige Costello (Asana)“Tell me about a time something went wrong — what did you do?”
Nikhyl Singhal (Facebook)“What does everyone take for granted that you think is hogwash?”
Ayo Omojola (Carbon Health)“Tell me something you did that worked, but not for the reason you thought.”
Scott Belsky (Adobe)“What have you learned about yourself that reveals a limitation in how you work?” / “Do you consider yourself lucky?”
Lauryn Isford (Notion)“Tell me about a time you delivered something impactful.”
Paul Adams (Intercom CPO)Reference check: “What feedback will I be giving this person in their first performance review?”