17 个面试题：看候选人到底怎么想

Lenny opens the episode by explaining that the lightning-round question about a favorite interview question has remained one of listeners' favorite segments. He says the compilation pulls 17 favorite interview questions from more than 100 guests into a single episode. The host frames it as useful for preparing to interview candidates, improving existing interview questions, or getting ready to be interviewed.

The episode is organized as a rapid sequence of guest clips rather than a single interview. Each guest names a question and explains what a strong answer reveals about a candidate. The result is a compact toolkit of prompts for probing judgment, self-awareness, agency, and communication.

Eeke De Miliano, former head of product at Retool and a former PM at Stripe, asks candidates, 'To what do you attribute your success?' with one constraint: they cannot say 'luck.' She explains that humble people often reach for luck, so banning it forces candidates to reflect on why they are where they are. That reflection, she says, reveals self-awareness, curiosity, and how they think about the world.

Geoff Charles, head of product at Ramp, asks, 'What's the hardest thing you've ever done?' He asks because working at Ramp is hard, and he wants to learn what 'hard' means to the candidate. He listens for why the work was difficult, how the candidate overcame it, how they worked with other people, and how much agency they had. A strong answer shows both the candidate's definition of difficulty and the effort they put into overcoming it.

Shishir Mehrotra, CEO and co-founder of Coda, uses a made-up scenario: a group of scientists has invented a teleportation device and hired the candidate as its business counterpart to bring it to market. The candidate can be a PM or any other role, and the opening question is simply, 'What do you do?' Most candidates generate many questions, so Shishir then raises the stakes: the scientists hate talking to people and will answer only two questions before expecting a plan. He watches for the one or two Eigenquestions that actually determine the answer.

One favorite answer asked, 'Is it safe enough for humans?' and, 'Is it more expensive CapEx or OpEx—is it more expensive to buy them or to run them?' From those two questions the candidate built quadrants. If the device is safe but cheap to buy and expensive to run, it might become a human fax machine placed everywhere; if it is expensive to buy but cheap to run, it might replace airports; if it is not safe for humans, the use cases shift to goods that are costly to transport.

Shishir argues that the fictional, low-stakes framing helps people learn the method, and he notes that children often reach two good Eigenquestions quickly. Some candidates ask about the device's size without explaining what decision that answer would unlock, which is the failure mode he is testing for. He also says Eigenquestions are everywhere: when his younger daughter asked why three gas stations sit on the same corner, the underlying question was how a gas station's placement is decided.

Yuhki Yamashita, chief product officer at Figma and former head of design at Uber, asks candidates to describe a time they were part of a controversial product decision and what they did. He finds the question revealing because strong candidates can set up the conflict, explain why the problem mattered, represent both sides, and stay even-keeled while showing they can take different perspectives. In a simpler variant, he asks candidates to talk about a big problem they worked on, then checks whether he feels compelled to work on that problem himself. A great PM, he says, can cast a problem as existential and interesting enough to rally the troops, which is a storytelling and communication test.

Katie Dill, head of design at Stripe; Karri Saarinen, CEO of Linear; and Camille Hearst, a product leader at Spotify and former product leader at Patreon, all share the same favorite question: 'Tell me what work you are most proud of?' The question helps them understand a candidate's taste, judgment, motivations, and sense of what counts as good work. Camille asks what the candidate is most proud of and why, in professional life or otherwise, because it indicates what the person values. Katie adds that spending time on something the candidate did well reveals motivations, work ethic, and what good looks like to them.

JZ, head of product at Webflow and a former Airbnb colleague of Lenny's, likes behavioral questions about challenging and ambiguous situations. She says the PM job is inherently ambiguous, so she looks for candidates who put structure and a path forward through the ambiguity. Strong answers also show that the candidate seeks help and inputs rather than pretending certainty, and that they define milestones for checking whether the chosen path is working.

Noah Weiss, chief product officer at Slack, asks, 'What unfair secrets have you learned to improve the velocity and energy level of a product team?' By 'unfair' or 'secret,' he means something the candidate probably did not read in the media. He wants to know what they learned, how they learned it, how it works, and how they apply it. The question also gives interviewers interesting bits of inspiration.

Ben Williams, former VP of product at Snyk and now an advisor to product-led growth startups, asks, 'Fast forward three years, what's different about you then?' Many candidates default to role or title aspirations, but he looks for humility and self-awareness about personal and professional growth. He also values openness about where someone needs to work on themselves. Across interviews, Ben looks for curiosity, comparing good PMs to his six-year-old son in how often they ask 'why.'

Ben also highlights a question a candidate once asked him: 'Tell me about the diversity, equity, inclusion and belonging initiatives that you've recently personally been involved with?' He calls it brilliant because it lets a candidate test whether their personal values align with those of someone they would work closely with. It flips the interview into a two-way evaluation of values.

Meltem Kuran Berkowitz, head of growth and a very early employee at Deel, asks, 'What would your siblings say about you?' If the candidate has no siblings, she asks what their parents would say. She looks for sincerity and self-awareness about how other people see them. A polished answer such as 'my siblings would say I'm very organized and bring the family together' probably sounds like a bullshit answer, while acknowledging weird or critical things shows the humility she wants.

Paige Costello, co-head of product management and head of AI at Asana, asks, 'Tell me about a time something went wrong. What was it? What did you do about it?' The question gets at product failures and team breakdowns, which are inevitable in the work. She evaluates the candidate's mindset, how they talk about the situation, and how they relate to evaluating it. It reveals how people think and perceive themselves when things are not working well.

Nikhyl Singhal, VP of product at Facebook, asks, 'What's something that everyone takes for granted that you think is essentially hogwash or inaccurate?' He adapts it to managers by asking what conventional wisdom they bet against after managing hundreds of people, and says it can be pointed at domains such as AI misconceptions. He is trying to break the interview mindset in which candidates spend the whole conversation predicting what the interviewer wants to hear. High-quality people can be dismissed when they are not genuine, and this question is hard to answer without offering a genuinely held opinion. He calls it a save question for candidates who might otherwise be dismissed for saying nothing new.

Ayo Omojola, chief product officer at Carbon Health, former product lead at Square, and a former founder, asks, 'Tell me something you did that worked out, but not for the reason that you thought it would work,' or, 'Tell me something you did that was a good decision that didn't work.' His process is about teasing out introspection. He wants to know whether a person is reflective about the decisions they have made, why those decisions worked or failed, and whether they incorporate that learning into their model so they make different decisions next time.

Scott Belsky, chief strategy officer at Adobe, former chief product officer of Adobe, and former founder of Behance, asks about something people have learned about themselves that reveals a limitation in how they work. The question tests introspection and whether someone can be open when they hit their limits or struggle, rather than blaming others and pointing fingers. He also likes asking, 'Do you consider yourself lucky?' He finds it fascinating because people who are insecure about how they got where they are may decline to admit luck, while comfortable people should admit it; in his view, everyone is very lucky and certainly privileged.

Lauryn Isford, head of growth at Notion and former head of growth at Airtable, asks, 'Tell me about a time that you delivered something that was impactful.' She wants the candidate to explain how they define impact and what it means to them. For a growth practitioner, a good answer shows intrinsic motivation to have an impact on the business.

Paul Adams, chief product officer at Intercom, closes the episode with advice for reference calls after a great candidate emerges from the interview process. Referees are usually the candidate's best collaborators and favorite managers, so he asks, 'What feedback will I be giving this person in their first performance review?' The question is powerful because the referee cannot easily dodge it: there is an answer, and it is often incredibly enlightening about the candidate's real development areas.