The best interview questions to ask candidates aren't the ones found in generic hiring guides — they're the ones that break through rehearsed answers and reveal how a person actually thinks. To find those questions, we compiled 17 favorites from top product leaders at companies like Figma, Slack, Stripe, Ramp, and Notion. Whether you're building an interview loop, refreshing your existing questions, or preparing for your next interview, this list is the only resource you'll need.

What Are the Best Interview Questions to Ask Candidates?

The best interview questions share a common trait: they're nearly impossible to fake. They either require genuine self-reflection, on-the-spot structured thinking, or a willingness to be vulnerable. The 17 questions below — sourced from over 100 conversations with top product leaders — cover all three dimensions. Here they are, with context on what great answers actually look like.

What Interview Questions Do Top Product Leaders Ask?

1. "To what do you attribute your success?" (No saying luck.)

Asked by: Eeke De Miliano, former Head of Product at Retool and PM at Stripe.

Humble candidates default to luck. This question removes that escape hatch and forces real self-reflection. What you're looking for is self-awareness and curiosity — does this person actually know why they are where they are? Candidates who have genuinely reflected on their trajectory reveal how they think about the world and their place in it.

2. "What's the hardest thing you've ever done?"

Asked by: Geoff Charles, Head of Product at Ramp.

This question surfaces what "hard" means to a candidate — and whether their threshold matches the demands of your team. Listen for how they overcame the difficulty, how they worked with others, and how much personal agency they exercised. It's not just about the story; it's about the texture of their resilience.

3. "What's something everyone takes for granted that you think is hogwash?"

Asked by: Nikhyl Singhal, VP of Product at Facebook.

Most interview answers are performance — candidates saying what they think you want to hear. This question makes that impossible. There's no safe, pre-packaged answer. You either have a genuine, well-reasoned contrarian view or you don't. It's Nikhyl's "save question" for high-quality candidates who might otherwise get dismissed for being too polished.

4. "Tell me about a time you were part of a controversial product decision."

Asked by: Yuhki Yamashita, Chief Product Officer at Figma.

Great product managers can hold two opposing views simultaneously and represent both sides fairly. This question tests exactly that. Can the candidate set up the conflict clearly? Can they explain why reasonable people disagreed? The best answers feel like a balanced case study, not a grievance. As a bonus probe: after the story, ask whether the candidate feels compelled to work on that problem — strong PMs make even mundane challenges sound existential.

5. "Tell me what work you are most proud of."

Asked by: Katie Dill (Stripe), Karri Saarine (Linear), and Camille Hearst (Spotify) — independently, all three named this their favorite question.

Three leaders from different companies converging on the same question is a signal worth paying attention to. What you learn: a candidate's taste, judgment, intrinsic motivation, and definition of a good outcome. It also creates space for the candidate to shine, which makes for a better conversation than leading with something negative.

6. "Tell me about a time you navigated significant ambiguity."

Asked by: JZ, Head of Product at Webflow.

The PM job is, by definition, ambiguous. What you want to see is someone who doesn't just survive uncertainty — they impose structure on it. Good answers show a candidate who sought input, laid out a path forward, defined small milestones to validate direction, and adjusted when the path proved wrong. Beware of anyone who makes ambiguous situations sound obvious in hindsight.

7. "What unfair secrets have you learned to improve team velocity and energy?"

Asked by: Noah Weiss, Chief Product Officer at Slack.

The keyword here is "unfair." You're explicitly not looking for something they read in a Medium article. You want something earned — a lesson from genuine trial and error that isn't common knowledge. This question also doubles as a learning opportunity: great candidates will teach you something.

8. "Fast forward three years — what's different about you then?"

Asked by: Ben Williams, former VP of Product at Snyk.

Most candidates interpret this as a question about role or title. The best answers are about personal and professional growth — specific areas the candidate knows they need to develop. It's a humility and self-awareness test disguised as a forward-looking question. Bonus: it also signals ambition and intentionality about growth.

9. "What would your siblings say about you?"

Asked by: Meltem Kuran Berkowitz, Head of Growth at Deel.

Family members, especially siblings, don't sugarcoat. This question forces candidates to imagine themselves through the lens of someone who has no incentive to be polite. If the answer sounds like a LinkedIn bio ("organized, always bringing the family together"), that's a red flag. The best answers include something a little unflattering — because that's what real self-awareness sounds like.

10. "Tell me about a time something went wrong."

Asked by: Paige Costello, Co-Head of Product and Head of AI at Asana.

Things go wrong in product work constantly. What matters is mindset. Does the candidate take ownership? Do they analyze what failed and why? Do they blame circumstances or teammates? This question is a window into how someone processes failure — one of the most important signals in any hiring decision.

11. "Tell me something you did that worked, but not for the reason you expected."

Asked by: Ayo Omojola, Chief Product Officer at Carbon Health.

This is one of the most underrated questions on this list. It specifically tests for intellectual honesty. Anyone can talk about a win. Can they acknowledge that they got lucky, or that their original hypothesis was wrong even though the outcome was right? That kind of introspection is rare — and it predicts good future decision-making far better than clean success stories do.

12. "Tell me something you learned about yourself that reveals a limitation in how you work."

Asked by: Scott Belsky, Chief Strategy Officer at Adobe.

Scott pairs this with a companion question: "Do you consider yourself lucky?" Together, they probe for ego and defensiveness. People who are secure in their accomplishments can admit both their limitations and their luck. People who aren't will dodge both. The willingness to say "I got lucky and here's where I struggle" is a strong predictor of coachability.

13. "Tell me about a time you delivered something impactful."

Asked by: Lauryn Isford, Head of Growth at Notion.

The interesting part isn't the story — it's how the candidate defines impact. For a growth practitioner especially, you're listening for intrinsic motivation tied to business outcomes, not just feature launches or shipping velocity. How someone frames impact tells you what they actually care about optimizing for.

What Is an Eigenquestion and Why Does It Matter?

One of the most creative interview formats on this list comes from Shishir Mehrotra, CEO of Coda. He calls it the Eigenquestion test, and it went viral on TikTok and Instagram Reels for good reason.

Here's how it works: Tell the candidate that a group of scientists have invented a teleportation device. They've hired the candidate to bring it to market. What do they do? Let the candidate ask questions about the device — then cut them off. Tell them the scientists will only answer two questions. What two do they ask?

The point isn't the teleportation scenario. The point is whether the candidate can identify the one or two questions whose answers determine everything else — the Eigenquestions. One candidate's answer stood out: Is it safe enough for humans? And is it more expensive to buy or to run? Those two questions alone map out four distinct go-to-market strategies. That's sharp thinking under artificial constraint — exactly what product work requires.

How Do You Evaluate Self-Awareness in an Interview?

Several questions on this list target self-awareness specifically, and for good reason. Self-aware candidates give better feedback, grow faster, and are less likely to protect ego at the expense of the team. Signals to watch for:

  • They include something unflattering without being prompted.
  • They separate outcomes from decisions — acknowledging when something worked despite bad reasoning, or failed despite good reasoning.
  • They don't default to team or circumstance when explaining failure.
  • They can name specific things they're working on, not vague platitudes about "continuing to grow."

How Do You Get Honest Answers in a Reference Check?

Even the best interview process has limits. Paul Adams, Chief Product Officer at Intercom, offers a single question that cuts through the noise of reference calls: "What feedback will I be giving this person in their first performance review?"

References are hand-picked by the candidate, so they're naturally positive. This question is different because it has a real, specific answer — and the reference knows it. They can't just say "they're a great person." They have to think about where the candidate actually struggles. The answers are often the most illuminating data point in the entire hiring process.

What Makes a Great Interview Answer Stand Out?

Across all 17 questions, the common thread in strong answers is the same: specificity, honesty, and structure. Great candidates don't give polished non-answers. They bring a real story, acknowledge what actually happened (including the messy parts), and can explain their reasoning at every step. They also make you want to work on the problem with them — because they frame challenges in ways that feel urgent and interesting, not bureaucratic and dull.

Use these questions in your next interview loop, mix and match based on role, and pay close attention not just to what candidates say — but to what they choose to share.