Conducting Interviews

"Can you explain to me what that means? In the abstract, what are the things that you're looking for in someone that you want to fill that role? And we can then excavate that, right? And make what is implicit... let's make that explicit. So we can make that explicit, we can turn it into a decision rubric, we can create a structured interview process out of that."

"Talk me through your biggest product flop. What happened and what did you do about it?... I think the rawer the answer in terms of how bad it was and why, the better."

"I like to ask people how they prepared for the interview. This is not, I can't take credit for this. My wife told me about, gave me this idea and I loved it. I think it was a16z partner. But I love the question because when you ask, hey, how did you prepare? You're really asking how does the person think? How did they plan? How did they take things seriously or not? What did they read? What did they do?"

"Tell me about the most difficult or challenging thing you've overcome in the last year in your life. It doesn't have to be work related, it could be personal. And I think it's a great way to just reset the atmosphere, make people dig a little bit deeper into who they are and be more vulnerable."

"I like asking what someone's top 10 accomplishments are. They hate it because it's like, 'Oh, God. Ugh.' But it's really interesting to understand the level of quantitative versus qualitative in their accomplishments, what they value. And also if it's a, 'Oh, I ran a hundred miles or I have a great family,' whatever it is, it's really interesting to get to know somebody and also what they value."

"We created a set of objective criteria that would be used and an interview methodology that would be used in every interview, which was the objective criteria would be our leadership principles, and the methodology would be behavioral based interviewing."

"I have to always clarify this, by this I mean not some award you won or some promotion you got, I mean something you built, or some product, some process, some organization you built... And I could basically then, once they get into that example, ask a lot of probing and follow-up questions and I could fill an entire hour interview just sticking with this one example."

"One of the most important things that I always ask people is what people who've worked with them would say are their greatest strengths and weaknesses."

"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 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, what good looks like to them..."

"I always give them a problem to solve. That is probably my favorite question... 'Hey Lenny, I have a friend. He's been legally deaf or hearing impaired his whole life, and he just got a new job that requires him to wake up significantly earlier than he normally does. And as you can imagine, traditional alarm clocks will not do it... Walk me through how you go about tackling this or solving this.'"

"Before we wrap, is there anything else? ... the interesting thing about that question, you can spend three hours with somebody... And at the very end you say, 'Hey, Susan, before we wrap, is there anything else?' And often, Lenny, the most important thing for that person to communicate comes out then."

"My first favorite is, so Lenny, are you legendary? ... I want to get a read on that person and how they respond to a purposely provocative question about themselves."

"I think interviewing is not a skill that comes naturally. People think it does. It does not... I really recommend... and my book has examples of rubrics, questions you can use. How do you really get at... Because it's hard to really evaluate someone in 30 minutes or 45 minutes."

"I would say the other question I really like to ask is, if the people that you most recently worked with were in a room and you weren't there, how would they talk about you?"

"I like to ask candidates how they would improve our business model. I think so many PMs come in with a point of view of the product... but don't actually understand the underlying mechanisms of how we make money."

"I actually look for that first principle bias. So I'll give people case studies of here's what we see, how do you know that this is true? And then I have them set up an experiment design. I want to see that they are sampling randomly."

"We're starting to do that now. So traditionally we would just use CoderPad or something like that to wipe boards or a problem... But now we're looking at can you use Vibe code to build something? How comfortable are you with these tools or how are you thinking about evolving with them as well?"

"Show your passion around the product itself, around the use case, around the customer. Show who you are and why you care. I think sometimes people just say, 'I want a product job.' But you have to be able to fall in love with the problem. You have to fall in love, not with the product, but I said the problem, right? The use case. What problem are you trying to solve? And if you can do that, you can be a great product manager even without a lot of experience."

"To what do you attribute your success? And you can't say luck... I always kind of wanted to know, 'How self aware are you, and how curious are you?'"

"My favorite interview question of all time is to ask people to describe a best practice that they learned in their career... and then you'd be like, 'Great. Tell me a situation where that best practice would not be applicable.'"

"I think my favorite interview question is, 'Tell me about a time where you needed to disagree with your management, where you needed to stand up or fight for a position against higher leadership or people in power.'"

"If you're early in your career, ask if you could be on interview teams, even if you're not hiring, because then you're starting to practice something that's really important as you want to grow your career later, which is it's really hiring and recruiting people."

"Why do you want to work here is what I really like to ask because it tells me a lot... I want to know if this person knows what it is that we do, if they did a minimum level of research and if they connect with our mission because we're going to talk about mission a lot and I don't want them to gloss over it."

"What are you world-class at and how do you know that you're at that? And the second part is almost more important... It tells me if people actually care about metrics, and I don't care what the metrics are, but just how do you know this to be true? It has to be more than like, 'Oh, because my boss loves me,' or 'Because my mom told me,'... I want to hear, 'I'm proud of having accomplished this.' And maybe if you have some numbers to show, that's also really important."

"What is the accomplishment, career accomplishment you're most proud of? Because it tells you how they measure their impact. Tells you a lot about what they care about, how they measure their impact."

"I always like to ask people, 'Well, why do you want to join our company? What is it about working with us that would be exciting for you? Why our company as opposed to another one?'"

"What is the most innovative thing you have done and why do you think it's innovative? And it's really interesting that there are some people that think they need to answer about the biggest invention that they've done, and there are some people that are very vulnerable and they talk about something very personal that they have innovated. It shows a lot of their character."

"Give me an example in a time where you had a disagreement with your manager... what did you do about it and how did you go? Because it showcase a lot about your character and are you willing to stand your ground and push up when you need to?"

"And immediately I noticed there was this real difference in how people would answer the questions. And some people didn't seem to understand what the question was trying to get at. And some people sounded really good because they'd say, 'Well, I'll tell you three things. Number one, number two, number three.' And then when I paid attention to my notes, I'd be like, 'Wait, their three ideas weren't actually good ideas. They just sounded like they knew what they were doing.'"

"That's how I feel about this interviewing. Is that the reason that some people don't do as well as they could on interviews is just because a lot of these interview questions are trick questions. When they say, 'Oh, how would you design a bathroom?' I used to think that meant, 'What do you want in a bathroom?' And that's not what it means at all. It means 'Who is the best customer for a bathroom? What would they want?' But if you haven't been trained in this, you wouldn't know."

"I love to ask, 'Tell me about a recent project that you're proud of.' I feel like a lot of interviews don't give people enough chance to shine, to talk about something that they did really, really well and hear about what made it so good and what are they proud of, and how did they achieve those amazing results."

"I have a framework for this. The pearl framework for answering questions like this is problem, epiphany, action, result and learning. It's a little bit like the star framework, but I want it all like, 'What's the problem that you thought was worth solving, a problem that I think is big enough? What's your epiphany? What's the insight that you had? Do you notice something that nobody else did and how valuable was it?'"

"My favorite strategy for interviewing people is to throw a theory at them... I'll make a connection in my head and I'll say, 'I want to run a theory by you. Do you think that the reason why you are really interested in this or you made that decision is actually because of this other thing that you told me a little bit about?'... It forces people to think in real time in front of you."

"What do you want to do your first 30 days? ... In B2B, if I don't hear from the VP of sales or the VP of product that I'm going to go meet customers, out, I'm out."

"Give them time. And I don't like to judge too harshly, but whether it's the first interview or the second, they got to sell you this pen. But it's not 'Sell me this pen,' it's 'Sell me this app.'"

"My favorite one is 'What questions do you have for me?' by far... it is again indicative of these things that people have thought through or not thought through or the depth that they're thinking or their interest in engagement in the role."

"I would be in charge of the stopwatch that would time us. And I'd say, 'Okay, our time's up.' ... I would observe. Paul, Robert and Trevor, my co-founders would be asking them all sorts of questions about their product and their technology... I would usually remain pretty silent. And so I don't think people even really noticed me. But I would be just watching them and sort of trying to observe as much as I could"

"The 10 minutes is kind of as long as you need, in most cases. Because we found when they were longer, like 20 minutes, you'd know in 10 minutes and be twiddling your thumbs trying to get through the interview for the next 10 minutes. So we kept them short so we could interview more people."

"One of the things that Elon Musk has said that I found it very valuable in my time, is that if you really want to interview somebody and they claim that they've done something, you ask them six levels down. You improved sales. How did you do that, exactly? Well, we improved the pipeline. How'd you do that, exactly? Oh, well, we made the pipeline more measurable by having things that could be. How did you know? What were the seven stages of the pipeline and what made you pick them? You go six levels down and you can really understand if somebody was the person who solved the problem or if they're the person who is claiming that they solved the problem."

"I do like to do behavioral questions... 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 actually put a path forward."

"Imagine I'm interviewing a person you worked with. Now answer in there, tell me about of the same situation... what was that story from the perspective of one of the people you worked with? I think it can show some really interesting self awareness."

"We think that there is a culture interview, there is a functional interview, and there is a technical interview, but they're designed to get at these notions of have they actually done this kind of work before? Have they been pulled or pushed in their career and are they your kind of human?"

"Just to ask the simple question even in the cover letter, of your last ex-bosses, how many would get on the phone and say, you're amazing? If there's any equivocation in the answer, great, move on."

"Think of a topic that you had to explain lately that was the most complex, and then explain it to me like I'm five... I want to see if somebody can break a complex problem down in a really simple way, and give me an intuition for it in a short amount of time."

"The thing that I find is both very illustrative and helpful is just asking people to talk about something they worked on that failed and talk about something they built that succeeded as well. But I think you just learn a lot about self-reflection and their passions."

"I often think ask people that... Ask about their projects and I try to go deeper. It's like why was this decision made? Why do you think the decision was made? And I might ask, 'Do you think it was the right decision or did you agree on it?'"

"The question that I like to ask is just tell me the story of your career... I always learn a lot about people from how they tell the story of their life and their career... I learn how the person approaches setbacks from a story... I learn whether a person is able to identify mistakes they made."

"I like to ask a hypothetical second order thinking question. For example, if everybody who has taken a COVID vaccine dies tonight, what happens in 12 months from now? Can you explain the world- from what happens to money, what happens to law? What happens to countries? What happens to the military? What happens to the stock market? What happens to the order of things?"

"interviews, actually we know, don't predict job performance. So, very little to no evidence would say interviews will predict how I perform on the job... We use skill assessments and trials as ways to predict job performance, but interviews are good at predicting affinity and culture fit."

"one of my favorite questions is just, what is a personality trait that defines you? So, really, one that you are filled with strength, but that also can be seen as something you're working to improve."

"One is teach me something that I don't already know. I think it's just an awesome way of seeing if someone's going to lean in and really figure out what you don't know and then how passionate they are about pitching what they do know I think is really fun."

"Teach me something. Actually, we just talked about that today. Teach me something. Yeah. I love getting someone to, not related to work, not related to their job, something in your life, something you find interesting, just teach me about it."

"Teach me something about growth that I don't already know. Because... it really gives you a sense of what this person thinks is the top of the stack in terms of the smartest thing they know. Whether you know it or not is irrelevant. But sometimes you actually do end up learning some stuff."

"I love to ask people, how would you explain a database to a three year old? ... it's so important to be able to explain things in a simple ring and have the storytelling to convince a kid and really explain technical terms to non-technical people."

"Every product person at every seniority level is given the same case study. And the case study is extraordinarily difficult. It requires you to think about many, many dimensions simultaneously, to think about data propagation issues. It gets quite technical."

"When was the last time you changed your mind about something really important and why?"

"Tell me about a time that you failed and what happened."

"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... I look for sincerity and self-awareness."

"I always have a presentation component to the interview process that checks for prepared thinking communication. And I recommend a prep call between the two of us before that presentation. And I actually will give feedback on the presentation. And what this gives me signal is what is it actually going to be like to work together?"

"Usually hiring manager screen, and I actually do the live problem solving at this screen. I actually think it weeds out the most people... I sometimes would say, 'Hey, do you have your laptop? Can you pull up our pricing page? Curious to get your thoughts, what would you want to change?'"

"For the longest time, they had... a founder had to interview you in order for you to receive an offer... With Stephen, it would be, you'd be chatting about philosophy for an hour and a half and it would very much just be like he would pick a topic out of thin air. It was impossible to prepare for, and then he would just go very, very deep and try and test the limits of your understanding."

"what is it that most frustrates you about... instead of why you're leaving, what frustrates you the most about where you're working right now? ... what's more interesting is they've been unable to fix it. And so, in asking this question, and probing, you kind of get quite good at getting a sense of what is their limit, what's the thing they found, and what did they get stuck with?"

"I generally like interview questions that allow us to kind of do some work together... 'Given where technology is at, if we were to rebuild email, how might we do that?' I just feel like getting into it and getting into the details and really watching each other exercise our craft I think is really important."

"I'm always curious about, what makes you come alive? I want to work with people that are alive, and connected, and inspired... I'm always looking for that energy first and skills second."

"I like to ask people about, what have you done that was hard that you're proud of? What have you done that was difficult? And what was it and why was it difficult and how did you get it done?"

"I like to ask people is, 'Okay, now imagine everything works out, all the challenges you're facing work out, all your plans work out, everything hits the top end of your vision for what this could be. What do you imagine is the impact of having done that? Who's being impacted by that? Why is that a big deal that happened?'"

"I ask them to teach me something new in one minute. Usually I'll pull up my phone and I'll start the timer. I'll give them a second to think about it and start the timer. They're graded on three different criteria. One is completeness. Did they actually finish the lesson inside of one minute? Two is complexity. ... And then last is really clarity. ... Did they convey the idea fully and wholly?"

"I have found that there's not one question that will get me the signal I actually want given how diverse the candidate's experiences might be... we just need people who can run through walls to accomplish big goals. Maybe grit and endurance in some ways and drive are the words I would throw out there."

"A group of scientists have invented a teleportation device... 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? ...all of a sudden the sharp product managers, engineers, so basically every role, they very quickly find what are the one or two eigenquestions on this topic."

"At the beginning of the loop, the person presents... about half the time is spent on them presenting whatever they want. They can talk about themselves. They can teach us something and then another half is we've given them a prompt... I want you to upper bound us. I want you to tell us what's really amazing here."

"When people describe an experience, you ask them the name of the person that they worked with back then. And you ask them, 'So when I call this person after our call, what do you think they're going to say about that?'... people are unable to project and invent on the spot something from the lens of another person talking about them."

"I tell people that almost every interview question should start with, 'Tell me about a time in your career when...' to give them permission or to set their expectation that I'm asking them to tell me about something they've actually done that is relevant to the topic that I'm probing."

"I ask almost everybody, 'Imagine that you had a really great day at work. What was it that you did on that day?' Because what I'm trying to figure out is left to their own devices, what do they go to naturally because it rewards them?"

"What's something that would not exist without your initiative?"

"We are okay with people using the tools because I think one of the worst things is like, if someone comes here and doesn't like using these tools... we do want to see how they think on their feet and hopefully they're not just taking what we're saying, putting it in a voice translator and sticking it into ChatGPT and getting the answer out."

"I'll typically pick up a product that they use most often and then I will be like, 'Okay, what if this product were to do this? Then what do you think, it makes sense? Don't think it makes sense? What about this? Okay, how would it evolve in six months? What would happen in 12 months and so on?'"

"One of the questions I ask in the behavioral interview at the start is, walk me through the story of you from college to now... interesting to see where people spend most of their time talking and where they don't, and also how they describe the other people on that journey."

"one of my favorite interview questions is asking, 'describe to me a time when you're part of controversial product decision, and what did you do,' and all those things. And I think it's really revealing because if they can set up this conflict and understand why this problem was really important and represent both sides in such that you can understand why that conflict existed in the first place, then they can do it in this even-keeled way, where you realize that they can take on these different perspectives."

"I like to ask anyone who's going to be in a customer facing role... to solve an unfamiliar problem using Zapier... I basically lay out for them a problem that I, as the customer want to solve, and have them build it for me live."

"We'll give people interviews where we say, 'Use whatever tools are available to build a website and let's see what product you're able to build in an hour.'"

"To a man with a hammer, everything looks like a nail... I want to be nodding along. I want to go, that's exactly what I would do or that's way smarter than my idea. And then I just leave them alone because I've found that anytime I try and pull them in a certain direction or coach them or whatever, it just doesn't work."

"Two questions. If they're a people manager, what is your leadership philosophy? The amount of leaders who have never thought about that is quite scary. And if you're just pure product chops, tell me your favorite product, product you're most passionate about, and why."

"We have this interview step called the life story where we try to figure out if, are all the experiences you've had up until now actually going to be... Does it show that you are a curious person with range? ... Your resume should be a why, like why did you go from this company to this?"

"I like to ask, 'Tell me about a time something went wrong. What was it? What did you do about it? Yada, yada.'... evaluating people's mindset, and the way they talk about it, and the way they relate to evaluating the situation."

"We actually gave you a work challenge. We said, 'This is the problem you're facing. How are you going to solve it?' ... We want to see the depth of thinking. They don't know the right answer because they don't have the right data. That's okay. But they at least need to show us how they approach the problem."

"I like asking about something people have learned about themselves that reveal the limitation in how they work. It's a way to test introspection... I also like the question, like, 'Do you consider yourself lucky?'"

"When I was at Uber, some days I would do six interviews back to back. I would just be in a conference room and at some point you can't even remember who you're talking to because you talk to so many people, one after another after another. You just have some scrambled notes you're trying to decode afterwards."

"The whole thing's gotten so performative. It's like interviewing is handing out Oscars..."

"We put everyone through a very consistent process... nothing is a trick question."

"Call 10 customers. Pick up the phone yourself. Don't ask a researcher."

"How many zeros at the end of 100 factorial? I want to see how people react to impossible problems."