My favorite interview questions from 100+ guests

Transcription for the video titled "My favorite interview questions from 100+ guests".


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Lenny (00:00)

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 about 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. 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. 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 to begin your free journey. That's This episode is brought to you by Epo. Epo 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 Epo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features. And EPO 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. EPO 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. EPO also makes it easy for you to share experiment insights with your team, sparking new ideas for the A-B testing flywheel. EPO powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out EPO at and 10x your experiment velocity. That's

Guest Speakers

Eeke De Miliano (03:21)

First up, we've got Eike De Miliano. Eike was the head of product at Retool. She was also a PM at Stripe. Currently, she's starting her own company. And so here's Eike sharing her favorite interview question. Eike De Miliano: "To what do you attribute your success and you can't say luck? 'Cause you know, I think humble people will always say luck in some way. And you know, I always kind of wanted it, like, how self-aware are you basically, and I think, and how curious are you? And I think humble people will always say luck in some way. And, you know, I always kind of wanted it 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 about how they think about the world."

Geoff Charles (03:57)

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. 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 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 had in overcoming that. Overcome that difficulty and how much agency they had in overcoming that. So, it's really a good sign around what is difficulty to them and how much work they put into overcoming that. 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.

Shishir Mehrotra (04:31)

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 Marocha sharing his favorite interview question. 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, product counterpart. What if this question actually worked well for any role, but say you could be a product manager for this thing, bring it to market, what do you do? That's the whole question, right? And 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? That's the whole question, right? And 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 disintegrate things or not? Does it need a receiver and a sender? 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 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 eigen questions on 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? And that was a, like a very like crisp way to get to like just safety. How reliable is it? It didn't ask how reliable it is. How many bits and middle is it? 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, just 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 how we're gonna run it. If 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 probably do is replace airports. Because airports are pretty strategically placed in places where people are trying to 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 people come up with, do you do the most expensive things? Do you do the, is teleporting people come up with like, you know, do you do the most expensive things or do you do like, you know, is teleporting, you know, people's replacement hearts, is that like a really demanding thing? So, but these two questions kind of, kind of get to 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. That question, by the way, if you ask a kid that question, the, you know, hey, new teleportation device, you know, you get to ask two questions. Like almost every kid will like quickly get to two pretty good eigen questions. Again, kids are incredibly good at simplifying these things down. It's actually a skill we like remove from ourselves. Like I'll see all your candidates tell me things like, well, I guess I would ask them what size it is. And like, like, yes, I would ask them what size it is. And like, why would you ask them what size? What decision is that going to allow you to make to know what size it is? And, you know, sometimes I can explain it, sometimes not. Don't get hired. But yeah, but actually the thing I'd say about it is there are eigen questions kind of everywhere. I mean, you can you can take any product out there. I'll do it with my kids a lot. They'll say, you know, I was just riding with with my younger daughter and she said, you can take any product out there. I'll do it with my kids a lot. And they'll say, you know, I was just riding with my younger daughter. And she said, you know, how come there's three gas stations like in the same corner? Why do people do that? 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 this answer?

Yuhki Yamashita (08:44)

This next interview question comes from Yuki Yamashita, Chief Product Officer at Figma. I can almost take anything and say, what is the question that really drives. Could I just answer? This next interview question comes from Yuki Yamashita, chief product officer at Figma, also a former head of design at Uber. Describe to me a time when you were part of a controversial product. And what does it do and all those things. And I think 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 in such a way that you can understand why that conflict existed in the first place and they can do it in this kind of even-keeled way where 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 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, I think a really great product manager kind of like casts something. It's like, well, this is why it's something. it's like, this is why it's so existential to listen, there's so interesting, and really riled a trip. So that's kind of one big thing of storytelling communication, because at the end of the day, like so much of our job is around that. Next, you'll hear from Katie Dill, head of design at Stripe, Kari Saarinen, CEO of Linear, and Camille Hurst, product leader at Spotify, former product Saarinen, CEO of Linear, and Camille Hurst, Product Leader at Spotify, former Product Leader at Patreon, who all share the same favorite interview question.

Katie Dill (09:56)

Camille Hurst, CEO of Linear, could you please tell me what work you are most proud of? I ask because it helps me understand your taste, judgment, motivations, and what work you view as good and a positive outcome. It also helps me understand what you like to do and where your passion lies.

Karri Saarinen (10:36)

I usually like to ask, "What are you most proud of in your professional or personal life, and why?" I think this gives me an indication of what the person values and how they think about things. I also think it's nice for people to share something they believe they did really well, as we can then spend time discussing it, rather than focusing on negative aspects. I like to ask people to tell me about something they are really proud of accomplishing, and to take me through the process. I want them to explain why they are proud of it. I find that you can learn so much about a person's motivations, work ethic, and what they care about, and what they consider to be an achievement.

Camille Hearst (11:02)

And I think those are all really important things to understand about a person if you're going to work closely with them. Next is Jay Z, head of product at Webflow, former Airbnb colleague, sharing his favorite interview question.

Jiaona Zhang (11:28)

I do like to ask behavioral questions, just really understand 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. 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. That's what you look for. 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 seeking help, seeking those inputs as opposed to being like, 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 get those inputs, be able to say like, this is the path. This is how I 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 is a big thing I look for. Next up is Noah Weiss, chief product officer at Slack.

Noah Weiss (12:43)

What unfair secrets have you learned to improve the velocity and energy level of a product? By unfair or secret, I usually mean something not commonly found on platforms like Medium. What did you learn? How did you learn it, and how does it work? How do you apply it? You also get amazing, interesting bits of inspiration from asking that.

Ben Williams (13:10)

This next question comes from the very solitary voice of Ben Williams, former VP of product at Snyk and now an advisor to product-led growth startups. Ben Williams, VP of product at Snyk. 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, 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 conversation. It's not really a question, but something I'm looking for. And then maybe I want to flip it because building on something that Adam Fishman was saying, his 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.

Meltem Kuran Berkowitz (14:41)

Next up is Meltem Kuran Berkowitz, head of growth and a very early employee at Deal. 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. What do you look for in their answer that gives you a sign that they're a good candidate or not? I look for sincerity and self-awareness. Like your siblings are never... I mean, I love my sister, but she'll probably shoot talk to 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, they'll say these weird things about me" that shows a little bit of self-awareness and humbleness that I wanna see in a person. Next is Paige Costello, co-head of product management and also head of AI at Asana.

Paige Costello (15:29)

I like to ask, tell me about a time something went wrong. What was it? What did you do about it? And effectively the question gets that 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 not working well. We are in the final stretch now.

Additional Guests

Nikhyl Singhal (16:13)

There are only five more interview questions to go. Next up is Nikhil Singhal, VP of Product at Facebook, also one of the most popular episodes of the podcast. 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 hundreds of people in your career. What's conventional wisdom that you bet against that you have found is actually inaccurate?" And you can do that for what people think about AI that's inaccurate, that everyone believes. You could do that for domains. You can do all kinds of things. I'm always looking 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 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.

Ayo Omojola (17:51)

This next question comes from Ayo Omodjalo, Chief Product Officer at Carbon Health, former product lead at Square, and also a former founder. 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 my process is just teasing out introspection. It's just like, are you a person who is reflective about the decisions you've made and why they worked and why they did not and incorporating that into your model so you make different decisions next time. Next up is Scott Belsky, Chief Strategy Officer at Adobe, former Chief Product Officer of Adobe, also a former founder of Behance.

Scott Belsky (18:20)

I like asking people about something they have learned about themselves that reveals the limitations in how they work. It's a way to test introspection. 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, "Do you consider yourself lucky?" I think it's a fascinating question because it also, you know, some people who are super insecure about 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 privileged. And, you know, I just think that that's always an interesting conversation. Our penultimate interview question comes from Lauren Isford, head of growth at Notion, former head of growth at Airtable.

Lauryn Isford (19:17)

From Lauren Isford, Head of Growth at Notion, former Head of Growth at Airtable: "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 a growth practitioner is intrinsic motivation about having an impact on the business. Our final interview question is actually advice for doing reference calls, which comes after finding someone great through your interview process.

Paul Adams

Paul Adams (19:46)

And this comes from Paul Adams, chief product officer at Intercom, with this killer Irish accent. 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. 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.

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