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Based on Lenny's Podcast data
Lenny's Knowledge Sketch · Interview Q Compilation

17 Best Interview
Questions & What to Listen For

17 Guest Experts
Product Leaders from Stripe, Figma, Slack, Adobe, Asana, Linear, Coda & more
COMPILED
Foundational

What Makes a Question Great?

SELF-AWARENESS
"There's no way to answer that question without being genuinely opinionated. I'm testing: is this person authentic?"
  • Reveals authentic thinking, not rehearsed answers
  • Forces reflection and genuine self-awareness
  • Shows how candidates navigate ambiguity and complexity
  • Uncovers what they truly value and care about
  • Moves beyond interview theater
The Questions

17 Powerful Interview Questions to Use

  • 1. Attribution: "To what do you attribute your success?" (Eeke De Miliano, Retool)
  • 2. Difficulty: "What's the hardest thing you've ever done?" (Geoff Charles, Ramp)
  • 3. Eigenquestion: "You're a PM for a teleportation device. Ask only 2 questions before presenting a plan." (Shishir Mehrotra, Coda)
  • 4. Conviction: "Describe a controversial product decision and what you did." (Yuhki Yamashita, Figma)
  • 6. Pride: "Tell me what work you are most proud of?" (Katie Dill, Stripe; Karri Saarinen, Linear; Camille Hearst, Spotify)
  • 7. Ambiguity: "When have you navigated ambiguous situations? How?" (Jiaona Zhang, Webflow)
  • 8. Unfair Secrets: "What unfair secrets have you learned to improve team velocity?" (Noah Weiss, Slack)
  • 9. Future Self: "Fast forward three years, what's different about you?" (Ben Williams, Snyk)
  • 10. Sibling Test: "What would your siblings say about you?" (Meltem Kuran Berkowitz, Deel)
  • 11–17: Failure stories, "something went wrong", contrary beliefs, lucky breaks, impact definition, and more
Why these 17 workEach forces candidates to be introspective, reveal their authentic judgment, and prove they can think, not just recite accomplishments.
What to Hear

The Signals Behind Each Question

  • Self-awareness: Do they reflect on their role in outcomes vs. blaming luck or others?
  • Genuine reflection: Can they articulate *why* something worked, and own what they didn't understand?
  • Handling ambiguity: Do they freeze or create structure? Do they seek input or assume they're right?
  • Learning loops: Do they ask "is this working?" and change course? Or stay committed to a failing path?
  • Authenticity: Can they answer without sliding into interview-speak mode?
Bad answers

Default answers about roles/titles. Hiding behind luck or blaming context. Refusing to admit mistakes or growth areas. Answering what they think you want.

Great answers

Specific, honest stories with nuance. Showing they tested, learned, and adapted. Admitting what they didn't know. Revealing values through what they chose to highlight.

Interviewer Tips

How to Ask & Listen

  • Get specific: When they give generic answers, push: "Why? What decision did that let you make?"
  • Let silence happen: The best answers come after a long pause, don't fill it
  • Test for curiosity: Do they ask "why" throughout the interview? That's the actual signal
  • Listen for sincerity: Real self-awareness shows humility, not perfection
  • Watch for diversity/belonging: Ask what they've done personally on DEI, it reveals values alignment
The reference call secret"What feedback will I be giving them in their first performance review?" The referee can't dodge it and you get the real story.
What Candidates Get Wrong

4 Interview Myths This Dismantles

✗Prepare scripted answersINSTEAD →✓ The questions force authenticity. Rehearsed answers get exposed. Be genuinely opinionated instead.
✗Tell the interviewer what they want to hearINSTEAD →✓ Interviewers are testing if you're real. The more genuine and opinionated you are, the better you do.
✗Always highlight wins and hide failuresINSTEAD →✓ Great candidates show failures they learned from. Self-awareness about what went wrong is a signal of maturity.
✗Assume luck doesn't matterINSTEAD →✓ Admitting luck and privilege shows confidence and humility. The best people are honest about both effort and fortune.
Based on a compilation episode of Lenny's Podcast. All ideas on this page are from the episode.Watch on YouTube
GO DEEPER IN THE EPISODE
03:21 Eeke De Miliano03:57 Geoff Charles04:31 Shishir Mehrotra08:44 Yuhki Yamashita09:56 Katie Dill10:36 Karri Saarinen11:02 Camille Hearst11:28 Jiaona Zhang12:43 Noah Weiss13:10 Ben Williams14:41 Meltem Kuran Berkowitz15:29 Paige Costello16:13 Nikhyl Singhal17:51 Ayo Omojola18:20 Scott Belsky19:17 Lauryn Isford19:46 Paul Adams
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