My favorite interview questions from 100+ guests

0:02Welcome to a very special episode of the podcast. Ever since I started this podcast, one of people's favorite segments continues to be the lighting 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.

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3:22First up, we've got Aika Demoliano. Aika was head of product at Ritual. She was also a PM at Stripe. Currently, she's actually starting her own company. And so here's Aika sharing her favorite interview question. 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 wanted to do like how self -aware are you basically? And I think in 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? Really says a lot about how they think about the world.

3:58Next 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. Yeah, 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 had in overcoming that. So it's a really good sign around what is difficulty to them. And how much work they put into overcoming that.

4:31Next 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. 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 business counterpart, bring this to market product counter for what it's a question actually worth a while for a new wall.

5:16But say, you could be a product manager for this thing, bring it to market. What do you do? That's the whole question. I mean, usually people will start asking a bunch of questions and say, we'll tell me more about this device. Like, what does it do? How does it work? Is it big? It's small? Is it fast? Does it disintegrate things? Does it need a receiver and a sender? Does it save? 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, down to any older questions. Turns out, the scientists, they can't ink talking to people.

5:48And 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, this sharp product manager's engineer, so basically every role, they very quickly find what are the two one or two eigen questions on this topic. And I don't write 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 question that I'd ask, one is, is it safe enough for humans or not? And I was a very like, crisp way to get to, like, just safety, how reliable is it?

6:27He didn't ask how reliable it is. I'm going to get some middleist, like, just tell me, it's safe enough for humans or not. And the second one is, is it more expensive cap extra effects? Is it more expensive to buy them or to run them? And then he took those two questions and he said, like, death of 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 vaccine 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.

6:58And this is, this is how I'm going to 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. It's like airports are pretty strategically placed in places where people are trying to, 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 like, do you do the most expensive things? Or do you do the like, you know, is is teleporting, you know, people's replacement hearts?

7:28Is that like a like a really demanding thing? So, but these two questions kind of kind of get to the heart of it. The questions totally made up like no teleportation device exists. You know, he's not yes. And I'd 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, eight new teleportation device, you know, you get to ask two questions. Almost every kid will like quickly get to two pretty good eigen questions. The kids are incredibly good at simplifying these things down. It's actually a skill we like, remove from ourself.

8:02Like I'll see, I'll let your candidates tell me things like, like, I guess I would ask them what size it is. And like, why would you ask them what's like, what, what, what decision is that going to allow you to make? To know what size it. And you know, sometimes I can explain it, but sometimes not. Don't get hired, but they'd be, uh, but then actually the, the thing I'd say about it is they're, I ain't in question ten everywhere. I mean, you could, you could 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, with my younger daughter. And she said, you know, how come there's three gas stations, like in the same corner?

8:32Why, why, why do people do that? You know, uh, that's a really, that's a really insightful observation. What's the eigen question? How do you place a gas station? You can almost take anything and say, what is the question that really drives your body to the answer? This next interview question comes from Yuki Yamashita, Chief Product Officer at Figma, also a former head of design at Uber. It described to me a time when you're part of like, controversial product assistant, right? And, you know, what does 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 and, and such that you can understand why that conflict is just in the first place.

9:16And 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, right? I think, or sometimes I just ask saying for basic things like, okay, talk about kind of like a big problem that you worked on. And that 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, cash something is like, this is why it's so existential close.

9:47And there's slides so interesting. I like really rally that trip. So that's kind of one big thing of like, storytelling communication because the thing they like so much of our job is around that. Next, you'll hear from Katie Dill, head of design at Stripe, Kari Sarnan, CEO of Linear, and Camille Hurst, product leader at Spotify, former product leader at Patreon, who all share the same favorite interview question. Tell me what work you're 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.

10:29It also helps me understand a little bit about what they like to do, and where their kind of like gravity pulls them. I think usually I like to ask, what is the kind of 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 how they think about things. And I also like, I think it's always nice that people can share something like, they think they do it really well. And we can spend time on it versus just like asking something like, more like negative things.

11:03I like to ask people to tell me about something they're really proud of that they accomplished and take me through the process and talk to me about why they're proud of it. And if I need to 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. Next is Jay -Z, head of product that Webflow, former Airbnb colleague, sharing her favorite interview question. I do like to do behavioral questions, it's really understanding like when they've been in challenging situations, when they've been in ambiguous situations, like how do they navigate ambiguity?

11:45Is it 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 counter. 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 is supposed to be 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.

12:21So 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 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. What unfair secrets have you learned to improve the velocity and energy level of a product team?

12:56Am I saying unfair or secret agent mean like, not something that you probably read on like, I mean, input the look, what did you learn how to do 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. This next question comes from the very solitary voice of Ben Williams, former VP of Product at Sneak and now an advisor to Product Lead Growth startups. 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.

13:39So, no, 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 on the confecuriosity. 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 is the theme of evaluating the people dimension of folks you're potentially going to work with when you're interviewing with a company.

14:21And 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 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. Next up is Melton, Quran 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 were your parents say about you, but it's very telling what do you think other people think of you?

15:01What do you look for in their answer that gives you a sign that they're a good candidate or not? I have a look for sincerity and self -awareness. Like your siblings are never, I mean, I love my sister, but she'll 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.

15:30Next is Paige Castello, co -head of product management and also head of AI at Asana. I like to ask, tell me about a time something went wrong. What was it? What did you do about it? Yeah, yeah. 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. It really tells you a lot about how people think and how they perceive themselves when things are not working well.

16:14We are in the final stretch now. There's 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 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.

16:52You 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 the 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 told me nothing though.

17:46But I don't want the interview process to penalize them. And this was my save question. This next question comes from I .O. Omujalo, 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 like my process is just teasing out in respect. Is just like, are you a person who is reflective about like the decisions you've made and why they're worth and why they did not and incorporating them to model so you make different sins next.

18:21Next up is Scott Belcey, Chief Strategy Officer at Adobe, Former Chief Product Officer of Adobe, also former founder of Behands. I like asking about something people have learned about themselves that reveal the limitation in how they work. 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, some people who are super insecure about where they are and how they got there might decline admitting luck.

19:05Those 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 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 Caretable. Tell me about a time that you delivered something that was impactful. I'm looking for someone to help me understand how they define him and what it means to them. I think a good answer for 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 the interview process.

19:54And this comes from Paul Adams, Chief Product Officer at Intercom with his killer Irish accent. I had to do referral calls so I could urge you and 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 to in their favorite managers. So this question is what feedback will I be giving this person in their first performance review? 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.

20:27Leave a comment either on the newsletter post or in 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.