The Best Interview Questions from Lenny’s Podcast

Lenny’s Podcast | ~2022

A compilation of 17 favourite interview questions drawn from over 100 guests on Lenny’s Podcast. Lenny Rachitsky introduces each question with the guest who contributed it and explains what the interviewer listens for in the answer.

Key ideas

1. The Eigenquestion test reveals prioritisation ability. Shishir Mehrotra’s teleportation-device question — given a fictional product and only two questions to ask before writing a strategy — separates candidates who generate many questions from those who identify the two that determine all downstream decisions. A child often does better than a trained adult; the skill is deliberately removing itself.
2. The best questions target self-awareness, not knowledge. Multiple guests converge on the same diagnostic goal: Eeke de Milliano‘s “to what do you attribute your success?” (you cannot answer “luck”), Geoff Charles‘s ‘what’s the hardest thing you’ve ever done?’, Yuhki Yamashita‘s “describe a controversial product decision”, and Scott Belsky‘s ‘do you consider yourself lucky?’ all probe whether a candidate has built a coherent and honest model of their own history and limits.
3. What you’re proud of reveals values, not résumé. Katie Dill, Karri Saarinen, and Camille Hearst independently converged on the same question: ‘tell me what work you are most proud of?’ It surfaces taste, motivations, and the candidate’s definition of a good outcome — information that no skills assessment provides.
4. Unfair secrets filter for genuine practitioners. Noah Weiss asks candidates what unfair secrets they have learned to improve the velocity and energy level of a product team. A media-trained answer to a ‘what do you know that isn’t widely known?’ question is nearly impossible; the question breaks the interview mindset.
5. Reference calls have a cheat code. Paul Adams asks referees ‘what feedback will I be giving this person in their first performance review?’ The referee cannot deflect — there is an answer — and the specificity of the response reveals far more than any direct question about strengths and weaknesses.

See also

• Shishir Mehrotra — Eigenquestion teleportation test
• Eeke de Milliano — attribution question
• Geoff Charles — hardest thing question
• Yuhki Yamashita — controversial product decision
• Katie Dill, Karri Saarinen, Camille Hearst — what work are you most proud of?
• Jiaona Zhang — navigating ambiguity
• Noah Weiss — unfair secrets
• Paul Adams — reference-call question
• Nikhyl Singhal — conventional wisdom question
• Ayo Omojola — good decision that did not work out