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.