My favorite interview questions from 100+ guests

This is a special episode of the podcast where I've curated my favorite interview questions from over a hundred podcast guests. Whether you're a hiring manager, a job seeker, or simply intrigued by the brilliant minds behind groundbreaking products, these questions offer unique insights into the strategies and philosophies that shape successful interviews. — Brought to you by Sendbird—The (all-in-one) communications API platform for mobile apps: https://sendbird.com/lenny | Eppo—Run reliable, impactful experiments: https://www.geteppo.com/ Find the transcript at: https://www.lennysnewsletter.com/p/my-favorite-interview-questions-from Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, you’ll hear from: (00:00) Lenny (03:21) Eeke De Miliano (03:57) Geoff Charles (04:31) Shishir Mehrotra (08:44) Yuhki Yamashita (09:56) Katie Dill (10:36) Karri Saarinen (11:02) Camille Hearst (11:28) Jiaona Zhang (12:43) Noah Weiss (13:10) Ben Williams (14:41) Meltem Kuran Berkowitz (15:29) Paige Costello (16:13) Nikhyl Singhal (17:51) Ayo Omojola (18:20) Scott Belsky (19:17) Lauryn Isford (19:46) Paul Adams Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:02Lenny Rachitsky?

  Welcome to a very special episode of the podcast. Ever since I started this podcast, one of people's favorite segments continues to be the lightning round, and in particular, a question I ask guests around their favorite interview question that they like to ask candidates and what they look for in a good answer. What we've done is we've picked my favorite interview questions that guests have shared. Out of over 100 guests on the podcast, we've got 17 of my favorite interview questions, all combined in this one episode. You can use this episode anytime you are preparing to interview candidates, if you want to improve your existing interview questions, or if you're about to get interviewed and you want to prepare for the kinds of questions that you might get in the interview process.

• 0:47Lenny Rachitsky?

  Before we dive in, let me tell you about a product called Sendbird, the all-in-one communications API platform designed for both web and mobile apps. In a world saturated with multi-channel communication, product teams are discovering the effectiveness of in-app communication. With Sendbird, businesses can elevate their in-app experience with decluttered and branded communication, featuring AI-powered chatbots, one-way messages, chat, video calls, and live stream capabilities, all tailored for commerce, marketing, and top-tier support. Forward-thinking companies such as Hinge, Patreon, Yahoo, Accolade, and more use Sendbird to build in-app communication experiences that drive engagement, conversion, and retention.

• 1:29Lenny Rachitsky?

  In-app communication has the highest conversion, highest engagement, and highest satisfaction of any communication channel. And when it comes to investing in this channel, trust Sendbird to take your in-app communication experience to the next level. Start today with Sendbird's free plan, and as a listener of Lenny's podcast, you'll get an additional two months of unlimited usage and access to all premium features, including creating your very own generative AI chatbot. Visit sendbird.com/Lenny to begin your free journey. That's sendbird.com/Lenny.

• 2:04Lenny Rachitsky?

  This episode is brought to you by Eppo. Eppo is a next-generation A/B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and DraftKings rely on Eppo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features. And Eppo helps you increase experimentation velocity while unlocking rigorous, deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform, where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own. Eppo does all that and more with advanced statistical methods that can help you shave

• 2:48Lenny Rachitsky?

  weeks off experiment time, an accessible UI for diving deeper into performance, and out-of-the-box reporting that helps you avoid annoying, prolonged analytic cycles. Eppo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A/B testing flywheel. Eppo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Eppo at geteppo.com/lenny and 10x your experiment velocity. That's geteppo.com/lenny. First up, we've got Aika Demilliano. Aika was Head of Product at Retool. She was also a PM at Stripe. Currently, she's actually starting her own company.

• 3:31Lenny Rachitsky?

  And so here's Aika sharing her favorite interview question.

• 3:36Speaker 01

  To what do you attribute your success? And you can't say luck. Because I think humble people will always say luck in some way. And I always kind of wondered, like, how self-aware are you, basically? And how curious are you? And I think people have really sort of gone back and reflected on, why are they where they are today really says a lot about how they think about the world.

• 3:58Lenny Rachitsky?

  Next up, we've got Jeff Charles, Head of Product at Ramp, and also just happens to be one of the most popular episodes of the podcast.

• 4:05Speaker 02

  I asked, what's the hardest thing you've ever done? And I asked that because working at Ramp is hard. I want to understand like what hard means for them. I want to understand why it was hard. I want to understand how they overcame that difficulty, how they worked with other people to overcome that difficulty and how much agency they they had in overcoming that. So it's a really, it's a really good sign around what is difficulty to them and how how much work they put into overcoming that.

• 4:31Lenny Rachitsky?

  Next up, we've got Shashir Marotra, CEO and co-founder of Coda. Funny enough, we posted this exact clip to TikTok and Instagram reels, and it blew up. It's one of the most popular clips we've ever put on our channels. By the way, did you know I have a TikTok and an Instagram channel? Just look up Lenny's podcast on TikTok or Instagram. Anyway, with that, here's Shashir Marotra sharing his favorite interview question.

• 4:57Shishir Mehrotra?

  It's a very simple question, and it's a coded I can question test. And the question is, a group of scientists have invented a teleportation device. They've hired you, Lenny, to be their their sort of business counterpart, bring this to market, product counterpart. What is the question actually worked well for any role? Let's say you would be a product manager for this thing, bring it to market, what do you do? That's the whole question. Right? So people, usually people will start asking a bunch of questions and say, well, tell me more about this device. Like, what does it do? How does it work? And, you know, is it is it big? Is it small? Is it fast? Does it like, does it disintegrate things or not? Does it need a receiver and a sender? Does it, you know, it's safe? Like, all these different questions come out. And at some point, I'll just let those questions come out.

• 5:41Shishir Mehrotra?

  And at some point, I'll say, okay, nice job doing all the questions. Turns out, these scientists, they kind of hate talking to people. And they're kind of annoyed by all your questions. And so they've decided that they will answer only two of your questions. And after that, they expect a plan. What two questions do you ask? And interestingly, all of a sudden, like, the sharp, you know, product managers, engineers, so like, basically every role. They very quickly find what are the two one or two item questions in this topic? And there's no right answer, but I'll tell you like one of my favorite ones as a product manager said, okay, if I had to ask two questions, the two questions I'd ask, one is, is it safe enough for humans or not?

• 6:21Shishir Mehrotra?

  And that was a like a very like crisp way to get to like just safety, how reliable is it? Didn't ask how reliable it is, how many bits in the middle is like, just tell me, is it safe enough for humans or not? And the second one is, is it more expensive CapEx or OpEx? Is it more expensive to buy them or to run them? And then he took those two questions and he said, like, get with those two questions. I can form these quadrants and you can say, oh, it's safe enough for humans and it's cheaper to, they're very cheap to buy, but expensive to run. Then you probably run them like human fax machines, like you put them everywhere you can. And you say, hey, look, it's expensive to use, but like you all have the ability to teleport anywhere you want. And this is, this is how we're gonna run it. On the other hand, they're very expensive to buy, but cheap to run.

• 7:03Shishir Mehrotra?

  You probably have to place them very strategically, in which case what you probably do is replace airports. It's like airports are pretty strategically placed in places where people are trying to, trying to get, get around places. If it's not safe enough for humans, then you've got a whole different class of use cases where you go value what goods are transported in very costly ways. And you know, people come up with like, you know, do you do the most expensive things? And do you do the like, you know, is, is teleporting, you know, people's replacement hearts? Is that like a, like a really demanding thing? So, but these two questions kind of, kind of get to the, the heart of it. The question's totally made up, like no teleportation device exists, at least not yet. And I find that people's ability to learn the method is significantly higher if it's low stakes.

• 7:45Shishir Mehrotra?

  That question, by the way, if you ask a kid that question, the, you know, a new teleportation device, you know, you get, you get to ask two questions. But almost every kid will like quickly get to two pretty good item questions. Again, kids are incredibly good at simplifying these things down. It's actually a skill we like. Remove from ourself. Like I'll see all your candidates tell me things like, I guess I would ask them what size it is. And like, why would you ask them what size? What, what, what decision is that going to allow you to make? To, to know what size it is. And you know, sometimes I can explain it, but sometimes not, don't get hired. But yeah, but then actually the thing I'd say about it is there are questions kind of everywhere. I mean, you could, you could take any product out there. I'll, I'll do it with my kids a lot and they'll say, you know, I was just riding with, with my younger daughter and she said, you know, how come there's three gas stations?

• 8:30Shishir Mehrotra?

  Like in the same corner. Why, why, why, why do people do that? Yep. Uh, that's a really, that's a really insightful observation. What's the question? How do you place a gas station? You can almost take anything and say, what is the question that really drives, drives this answer?

• 8:45Lenny Rachitsky?

  This next interview question comes from Yuhki Yamashita, Chief Product Officer at Figma, also a former head of design at Uber.

• 8:53Yuhki Yamashita?

  Describe to me a time when you're part of a controversial product assistant, right? And you know, what does it do and all those things. And I, I think it's, it's really revealing because, you know, if they can kind of like set up this conflict and understand like why this problem is really important and represent both sides and, and such that you can understand why that conflict existed in the first place. And they can do it in this kind of like even keeled way where you, you realize that they can take on these different perspectives. Like you start to learn a lot about that person, I think. Or sometimes I just ask them for basic things like, okay, talk about kind of like a big problem that you worked on. And the thought experiment for me is always like, coming out of that, do I feel compelled to work on that problem?

• 9:37Yuhki Yamashita?

  Right? And no matter how boring it sounds on the surface, like I think a really great product manager kind of like, cast something as like, well, this is why it's so existential. And this slide is so interesting. I like really rallied it. So that's kind of one big thing of like storytelling, communication, because at the end of the day, like so much of our job is around that.

• 9:57Lenny Rachitsky?

  Next, you'll hear from Katie Dill, Head of Design at Stripe, Kari Sarnen, CEO of Linear, and Camille Hearst, Product Leader at Spotify, former Product Leader at Patreon, who all share the same favorite interview question.

• 10:12Katie Dill?

  Tell me what work you are most proud of. And the reason I ask that is because, well, it helps me understand their taste and their judgment, what motivates them, what work they view as good and as a good outcome. It also helps me understand a little bit about, you know, what they like to do and where, you know, their kind of like gravity pulls them.

• 10:37Speaker 06

  I think usually I like to ask, like, what is the candidate most proud of and why? Like on their professional life or otherwise, like what they're most proud of and why. But I think it's kind of like, gives you a little bit indication like what the person values and like how they think about things. And I also like, I think it's always nice that people can share something like they think they did really well. And we can spend time on it versus just like asking something like more like negative things.

• 11:03Speaker 07

  I like to ask people to tell me about something they're really proud of, that they accomplished and take me through the process and tell, talk to me about why they're proud of it. And divine, you can learn so much about a person's motivations, about their work ethic, about what they care about, like what good looks like to them. And I think those are all really important things to understand about a person if you're going to work closely with them.

• 11:29Lenny Rachitsky?

  Next is Jay Z, head of product at Webflow, former Airbnb colleague, sharing her favorite interview question.

• 11:35Jiaona Zhang?

  I do like to do behavioral questions, just really understanding like when they've been in challenging situations, when they've been in ambiguous situations, like how do they navigate ambiguity is a big one for me. Because at the end of the day, like the PM job is really ambiguous. Like it's really hard to describe on a piece of paper, all the things that you're going to encounter. Good answers are people who put structure and a way forward through the ambiguity. Like that's what you look for. Like you want your PM to not just be like, oh no, we're swimming in ambiguity, but like actually put a path forward. I think also looking for people who are like seeking help, seeking those inputs as opposed to be like, yep, this is the way. This is very clear because again, the chances of whatever path you chart out for any product,

• 12:17Jiaona Zhang?

  for anything that you're doing is like the right path from the first time that you do it, so rare. And so I want to see someone be able to like get those inputs, be able to like say like, this is the path. This is how I like learned why, you know, I put this path together. And then going back to a lot of the stuff, I think we touched upon in this, this podcast is like, what are the little milestones that make you say, hey, is this working? Is this not working? And then make you either make a different decision, seeing people do that really well is a big thing I look for.

• 12:44Lenny Rachitsky?

  Next up is Noah Weiss, Chief Product Officer at Slack.

• 12:49Speaker 09

  What unfair secrets have you learned to improve the velocity and energy level of a product team?

• 12:56Speaker 09

  In my second unfair or secret, I usually mean like not something that you probably read on like a medium put that like what did you learn, how did you learn it? And how does it work and how do you apply it? You also just get amazing, interesting like bits of inspiration from asking that.

• 13:11Lenny Rachitsky?

  This next question comes from the very solitary voice of Ben Williams, former VP of Product at Sneak, and now an advisor to product-led growth startups.

• 13:22Speaker 10

  Fast forward three years, what's different about you then? A lot of people will default to telling you where they aspire to be in terms of role or title. But what I'm really looking for is signals of humility, of self-awareness around areas of personal and professional growth. So, you know, people who can be open about where they think they need to work on to grow themselves as people. I love that. Also, just generally throughout interviews, I'm looking for curiosity. So day to day, good PMs will be asking why as much as my six-year-old son does, which is a lot. So I'll try and discern that through the course of the conversations. Not really a question, but something I'm looking for.

• 14:08Speaker 10

  And then maybe I want to flip it because building on something that Adam Fishman was saying is theme of evaluating the people dimension of folks you're potentially going to work with when you're interviewing with a company. And this was a question I got asked myself recently by a candidate, which I just thought was brilliant. And that was, tell me about the diversity, equity, inclusion and belonging initiatives that you've recently personally been involved with. And that it just felt like a really great way for them to be able to test alignment of their personal values with those of someone they'd be working with really closely. So I love that.

• 14:42Lenny Rachitsky?

  Next up is Meltem Kuran-Berkowitz, Head of Growth and a very early employee at Deal.

• 14:48Speaker 11

  What would your siblings say about you? It's very telling if they have siblings. If they don't, I will say, what would your parents say about you? But it's very telling what you think other people think of you.

• 15:01Lenny Rachitsky?

  What do you look for in their answer that gives you a sign that they're a good candidate or not?

• 15:05Speaker 11

  I look for sincerity and self-awareness. Like, your siblings are never, I mean, I love my sister, but she probably should talk me a lot. And being aware of that is very important. Like, if someone's like, "My siblings will say I'm very organized," and that I'm the one that brings our family together, like, that's probably a bullshit answer. But if they're like, "Oh, yeah," like, they'll say these weird things about me that shows a little bit of, like, self-awareness and humbleness that I want to see in a person.

• 15:30Lenny Rachitsky?

  Next is Paige Costello, co-head of product management and also head of AI at Asana.

• 15:37Speaker 12

  I like to ask, "Tell me about a time something went wrong. What was it? What did you do about it?" Yada, yada. And effectively, the question gets that. When, when the product failed, when something about the team didn't work, just things that go wrong, because that's what happens when you're doing this work. And evaluating people's mindset and the way they talk about it and the way they relate to evaluating the situation, I think it's a great question. It really tells you a lot about how people think and how they perceive themselves when things are not working well.

• 16:14Lenny Rachitsky?

  We are in the final stretch now. There's only five more interview questions to go. Next up is Nikhil Singal, VP of Product at Facebook, also one of the most popular episodes of the podcast.

• 16:25Nikhyl Singhal?

  What's something that everyone takes for granted that you think is essentially hogwash or inaccurate? You know, sometimes I'll ask a manager, "Look, you've managed, you know, hundreds of people in your career. What's conventional wisdom that you bet against that you have found exactly, actually, inaccurate?" And you could do that for, "What do people think about AI that's inaccurate that everyone believes?" You could do that for, you know, domains. You can do all kinds of things. I'm always looking to, for people to break this sort of interview mindset. So- Everyone always prepares for interviews and then their entire conversation is predicting

• 17:08Nikhyl Singhal?

  what you think you want me to say. And as a result, you can have high-quality people that you dismiss because they weren't genuine. There's no way to answer that question without being genuinely opinionated. Because it starts with, what is the thing that you think I want to say here and then tell me why it's inaccurate. So when I break that wall, I'm testing, is this person authentic? Because sometimes I'm dismissing them because they gave me, they told me nothing new. But I don't want the interview process to penalize them. And this was my save question.

• 17:52Lenny Rachitsky?

  This next question comes from Iyo Omajalo, Chief Product Officer at Carbon Health, former product lead at Square, and also a former founder.

• 18:01Speaker 14

  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. A lot of like my process is just teasing out introspection. It's just like, are you a person who is reflective about like the decisions you've made and why they worked and why they did not, and incorporating them to your model so you make difference as soon as next time?

• 18:21Lenny Rachitsky?

  Next up is Scott Belsky, Chief Strategy Officer at Adobe, former Chief Product Officer of Adobe, also former founder of Behance.

• 18:30Scott Belsky?

  I like asking about something people have learned about themselves that reveal the limitation in how they work. You know, it's a way to test like introspection. And when this person hits their limits or struggles, can they be open and introspective? Or are they going to blame and point fingers? So I do ask that. I also like the question, like, do you consider yourself lucky? I think it's a fascinating question. Because it also, you know, some people who are super insecure about, you know, where they are and how they got there might decline admitting luck. You know, those who are comfortable should admit that they were lucky. I mean, I think the truth is, we're all very lucky and certainly

• 19:13Scott Belsky?

  privileged. And, you know, I just think that that's always an interesting conversation.

• 19:17Lenny Rachitsky?

  Our penultimate interview question comes from Lauren Isford, Head of Growth at Notion, former Head of Growth at Airtable.

• 19:25Speaker 16

  Tell me about a time that you delivered something that was impactful. I'm looking for someone to help me understand how they define impact and what it means to them. I think a good answer for growth practitioner is intrinsic motivation about having an impact on the business.

• 19:46Lenny Rachitsky?

  Our final interview question is actually advice for doing reference calls, which comes after finding someone great through your interview process. And this comes from Paul Adams, Chief Product Officer at Intercom with his killer Irish accent.

• 20:00Paul Adams?

  I had to do referral calls. So like you're interviewing someone, you want to give them the job and they've got referees. And of course, the referees they have are like the best people that they've ever worked with and their favorite managers. So this question is, what feedback will I be giving this person in their first performance review? That's an amazing question because the person can't dodge it, you know, there's an answer and it's incredibly enlightening.

• 20:23Lenny Rachitsky?

  And it's a wrap. Thank you so much for listening. I hope you found this valuable. Leave a comment either on the newsletter post or in the YouTube comments or even on Twitter. Let me know what you think. If there's a great response, we'll continue to do this. If not, we'll never do this again. All right. Thank you. Enjoy.