My favorite interview questions from 100+ guests

1. 0:00 – 3:21

   Lenny

   1. LRLenny Rachitsky0:00

      (instrumental music) . 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 a hundred 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. Before we dive in, let me tell you about our 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. 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. 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 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.

2. 3:21 – 3:57

   Eeke De Miliano

   1. LRLenny Rachitsky3:22

      First up, we've got Eka Damiliano. Eka was head of product at Retool. She was also a PM at Stripe. Currently, she's actually starting her own company. And so here's Eka sharing her favorite interview question.

   2. RVRahul Vohra3:36

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

3. 3:57 – 4:31

   Geoff Charles

   1. RVRahul Vohra3:57

      about how they think about the world.

   2. LRLenny Rachitsky3:58

      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.

   3. JCJeff Charles4:05

      I ask, "What's the hardest thing you've ever done?" And I ask that because working at Ramp is hard, and 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, and how, how much work they put into overcoming

4. 4:31 – 8:44

   Shishir Mehrotra

   1. JCJeff Charles4:31

      that.

   2. LRLenny Rachitsky4:31

      Next up we've got Shishir Mehrotra, 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 Shishir Mehrotra sharing his favorite interview question.

   3. SMShishir Mehrotra4:57

      It's a very simple question, and it's a coded eigenquestion test. And the question is, a group of scientists have invented a teleportation device. They've hired you, Lenny, to be their, uh, their sort of business counterpart, bring this to market ............................ This question actually worked well for any role. But say you could be a project manager for this thing, bring it to market, what do you do? That's, that's the whole question, right? So, 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, uh, is it big? Is it small? Is it fast? Is it, like, does it disintegrate things or not? Does it need a receiver and a sender? Does it, you know, is it safe?" Like, all these different questions come out. And at some point, I'll just let those questions come out. And at some point, I'll say, "Okay, nice job generating 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, in basically every role...... they very quickly find what are the two, one or two eigenquestions on this topic. And there's no right answer, but I'll tell you, like, one of my favorite ones is a product manager said, "Okay, if I had to as- ask two questions, the two questions I would ask, one is, is it safe enough for humans or not?" And that was a, like, a very, like, crisp way to get to, like, just safety, how reliable is it? He didn't ask how reliable it is, how many bits in the middle he's like, "Just tell me, is this 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, "Just with those two questions, I can form these quadrants." You could 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 going to run it." But with the other hand, they're very expensive to buy but cheap to run, you probably have to place them very strategically, in which case what you'd probably do is we place airports, 'cause, 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 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 or do you do the like, you know... The... Is- is teleporting, you know, people's replacement hearts, is that like a- like a really demanding thing to do? So- so but these two questions kind of- kind of get to the- the- the heart of it. The question's totally made up, like n- no- no teleportation device exists or at l- least not yet. And I find that people's ability to learn the method is significantly higher if it's low stakes. That question, by the way, if you ask a kid that question, the, you know, "Hey, new teleportation device, you know, you get- you get to ask two questions," almost every kid will, like, quickly get the two pretty good eigenquestions. Again, kids are incredibly good at simplifying these things down. It's actually a skill we, like, remove from ourselves. Like, I'll see- I'll hear candidates telling me things like, "Well, I guess I would ask them what- what size it is." I'm like, "Why would you ask them what size? What- what- what decision is that gonna allow you to make t- to know what size it is?" And, you know, sometimes they can explain it and sometimes not and don't get hired but the, uh... But, actually, the- the thing I'd say about it is there are eigenquestions kind of everywhere. I mean, so 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... Uh, I was just riding with- with my younger daughter and she said, you know, "How come there's three gas stations, like, in the same corner? Like, why- why- why do- why do people do that?" It's a, you know... Uh, that's a really- that's a really insightful observation, what's the eigenquestion? How do you place a gas station? You can almost take anything and say, "What is the question that really drives- drives this

5. 8:44 – 9:56

   Yuhki Yamashita

   1. SMShishir Mehrotra8:44

      answer?"

   2. LRLenny Rachitsky8:45

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

   3. YYYuhki Yamashita8:53

      Describe to me a time when you were part of a controversial product decision, right? And, you know, what did you 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 was really important and represent both sides in a... In such that you can understand why that conflict ex- 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, t- 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, right? And no matter how boring it sounds on the surface, like, I think a really great product manager kind of, like, can cast something as, like, "Well, this is why it's s- so existential for us and this is why it's so interesting," and, like, really rally the troops, so... That's kind of one big thing of, like, storytelling communication because at the end of the day, like, so much of our

6. 9:56 – 10:36

   Katie Dill

   1. YYYuhki Yamashita9:56

      job is around that.

   2. LRLenny Rachitsky9:57

      Next, you'll hear from Katy Gill, head of design at Stripe; Karri Saaranen, CEO of Linear; and Camille Hearst, product leader at Spotify, former product leader at Patreon, who all share the same favorite interview question.

   3. KGKaty Gill10:12

      "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, uh, and where, you know, their kind of, like, gravity

7. 10:36 – 11:02

   Karri Saarinen

   1. KGKaty Gill10:36

      pulls them.

   2. KSKarri Saarinen10:37

      I think usually I- I like to ask, like, what is the candidate most proud of and why, like, um, 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- and, like, how they think about things and- and also, like, I think it's always nice that people can share something that they think they did really well and we can spend time on it versus just, like, asking something, like, more

8. 11:02 – 11:28

   Camille Hearst

   1. KSKarri Saarinen11:02

      like negative things.

   2. CHCamille Hearst11:03

      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. I find 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

9. 11:28 – 12:43

   Jiaona Zhang

   1. CHCamille Hearst11:28

      with them.

   2. LRLenny Rachitsky11:29

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

   3. JZJZ (Jiaona Zhang)11:35

      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- 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- 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 being like, "Yep, this is the way, this is very clear." Because again, the chances of whatever path you chart out for any product, 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..."... learn 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 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 i-

10. 12:43 – 13:10

    Noah Weiss

    1. JZJZ (Jiaona Zhang)12:43

       is- is a big thing I look for.

    2. LRLenny Rachitsky12:44

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

    3. NWNoah Weiss12:49

       What unfair secrets have you learned to improve the velocity and energy level of a product team? And when I say unfair or you- in secret, I usually mean like not something that you probably read on like a Medium

    4. NANarrator13:01

       (instrumental music)

    5. NWNoah Weiss13:02

       ... post, but 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

11. 13:10 – 14:41

    Ben Williams

    1. NWNoah Weiss13:10

       from asking that.

    2. LRLenny Rachitsky13:11

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

    3. BWBen Williams13:22

       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- to grow themselves as people. I love that. Also, s- 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 (laughs) is a lot. So I'll try and discern that through the course of the conversation. It's not really a question, but something I'm looking for. And then maybe I- I wanna flip it, because building on something, um, that Adam Fishman was saying, his theme of evaluating the- the people dimension of folks you're potentially gonna 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,

12. 14:41 – 15:29

    Meltem Kuran Berkowitz

    1. BWBen Williams14:41

       I love that.

    2. LRLenny Rachitsky14:42

       Next up is Meltem Kuran Berkowicz, Head of Growth and a very early employee at Deel.

    3. MBMeltem Kuran Berkowicz14:49

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

    4. LRLenny Rachitsky15:01

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

    5. MBMeltem Kuran Berkowicz15:05

       I look for sincerity and self-awareness. Like, your siblings are never... I mean, I love my sister, but she probably should tell me a lot. And being aware of that is very important. Like, if someone was 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, "Ah, 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

13. 15:29 – 16:13

    Paige Costello

    1. MBMeltem Kuran Berkowicz15:29

       see in a person.

    2. LRLenny Rachitsky15:30

       Next is Paige Costello, Co-Head of Product Management and also Head of AI at Asana.

    3. PCPaige Costello15:37

       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 at 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. Really tells you a lot about how people think and how they perceive themselves when things are

14. 16:13 – 17:51

    Nikhyl Singhal

    1. PCPaige Costello16:13

       not working well.

    2. LRLenny Rachitsky16:15

       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.

    3. NSNikhyl Singhal16:25

       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 is accurately- 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 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 (laughs) why it's inaccurate." So when I break that wall, I'm testing, is this person authentic? 'Cause 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.

15. 17:51 – 18:20

    Ayo Omojola

    1. NSNikhyl Singhal17:52

    2. LRLenny Rachitsky17:52

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

    3. AOAyo Omojola18:01

       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 then incorporating that into your model so you make different

16. 18:20 – 19:17

    Scott Belsky

    1. AOAyo Omojola18:20

       decisions next time?

    2. LRLenny Rachitsky18:21

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

    3. SBScott Belsky18:30

       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 once this person hits their limits or struggles, can they be open and introspective or are they gonna blame and point fingers? So, I do ask that. I also like the question, like, "Do you consider yourself lucky?" I think that's a fascinating question because it also, you know, some people who are super insecure about, you know, where, where they are and how they got there might decline, uh, 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, uh, and certainly privileged and, you know, I just think that that's always an interesting conversation.

17. 19:17 – 19:46

    Lauryn Isford

    1. SBScott Belsky19:17

    2. LRLenny Rachitsky19:18

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

    3. LILauren Isford19:26

       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.

18. 19:46 – 20:45

    Paul Adams

    1. LILauren Isford19:46

    2. LRLenny Rachitsky19:46

       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.

    3. SPShane Parrish20:00

       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 ever worked with and their favorite managers. So this question is, "What feedback will I be giving this person in their first performance review?" And it's an amazing question because the person can't dodge it, you know? There's an answer and it's incredibly enlightening.

    4. LRLenny Rachitsky20:23

       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.

Episode duration: 20:45