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My favorite interview questions from 100+ guests

Lenny Rachitsky - Favorite interview questions all combined

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“This is a special episode of the podcast where I’ve curated my favorite interview questions that guests have shared, among over 100 podcast guests. Whether you’re a hiring manager, currently interviewing, or simply intrigued by the creative and perceptive questions that top product leaders rely on to find top talent, these questions offer unique insights into the strategies and philosophies that shape successful interviews.” - Lenny / ↗️

Episode⁠

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Lenny's Questions

Lenny's Questions

Question

To Look For

Who

To what do you attribute your success?

You can't say "luck". I always kind of want to know, how self-aware are you, basically, and how curious are you? I think people have really sort of gone back and reflected on why are they where they are today really says a lot about how they think about the world.

Eeko De Miliano

Head of Product at Retool

What's the hardest thing you've ever done?

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

Geoff Charles

VP of Product at Ramp

A group of scientists have invented a teleportation device. They've hired you to be their business counterpart, bring this to market, product fit. What two questions do you ask to those scientists?

It's a very simple question, and it's a coded Eigenquestion test. Interestingly, all of a sudden the sharp product managers, engineers, basically every role, they very quickly find what are the one or two Eigenquestions on this topic.

Two questions kind of get to the heart of it. The question is totally made up. No teleportation device exists, at least not yet. I find that people's ability to learn the method is significantly higher if it's low stakes.

Bonus Link:

https://coda.io/@shishir/eigenquestions-the-art-of-framing-problems/eigenquestions-3

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Shishir Mehrotra

CEO, and Co-founder of Coda

Describe to me a time when you were part of a controversial product decision. What did you do?

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 and such 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, you start to learn a lot about that person, I think.

Yuhki Yamashita

Chief Product Officer at Figma

Talk about a big problem that you worked on.

The thought experiment for me is always, coming out of that, do I feel compelled to work on that problem? Right? No matter how boring it sounds on the surface, I think a really great product manager kind of casts something. It's like, "Well, this is why it's so existential and this is why it's so interesting, and really rallied the troops up. That's kind of one big thing of storytelling and communication, because at the end of the day, so much of our job is around that.

Yuhki Yamashita

Chief Product Officer at Figma

Tell me what work you are most proud of?

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 what they like to do and where their gravity pulls them.

Katie Dill

Head of Design at Stripe

Tell me about something they're really proud of that they accomplished, 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, and I think those are all really important things to understand about a person if you're going to work closely with them.

Camille Hearst

Head of Fan Monetization at Spotify

Behavioral questions - Just really understanding, when they've been in challenging situations, when they've been in ambiguous situations, how do they navigate?

Ambiguity is a big one for me, because at the end of the day, 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.

I want to see someone be able to get those inputs, be able to say, "This is the path. This is how I learned why I put this path together."

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.

Jiaona Zhang

SVP of Product at Webflow

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

When I say "unfair" or "secret", I usually mean not something that you probably read on a media. "What did you learn? How did you learn it? How does it work, and how do you apply it?

Noah Weiss

Chief Product Officer at Slack

Fast forward three years, what's different about you then?

What I'm really looking for is signals of humility, of self-awareness, around areas of personal and professional growth. People who can be open about where they think they need to work on to grow themselves as people. I love that.

Generally throughout interviews, I'm looking for curiosity. 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.

Ben Williams

Advisor to product-led growth startups

Tell me about the diversity, equity, inclusion and belonging initiatives that you've recently personally been involved with?

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.

Ben Williams

Advisor to product-led growth startups

What would your siblings say about you?

What will your parents say about you?

I look for sincerity and self-awareness. Your siblings are never ... I mean, I love my sister, but she'll call me. She'll talk to me a lot. Being aware of that is very important. If someone was like, "My siblings will say I'm very organized and that I'm the one that brings our family together," 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 want to see in a person.

Meltem Kuran Berkowitz

Head of Growth at Deel

Tell me about a time something went wrong. What was it? What did you do about it?

Effectively, the question gets at, 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. Evaluating people's mindset, 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.

Paige Costello

Co-Head of Product Management, Head of AI at Asana

What's something that everyone takes for granted that you think is essentially hogwash or inaccurate?

I'm always looking for people to break this sort of interview mindset. Everyone always prepares for interviews, and then their entire conversation is predicting what you think you want me to say. 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 sit here and then tell me why it's inaccurate." When I break that wall, I'm testing, is this person authentic? Because sometimes I'm dismissing them because they told me nothing new. But I don't want the interview process to penalize them, and this was my save question.

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 could do that for, "What do people think about AI that's inaccurate, that everyone believes?" You could do that for domains. You can do all kinds of things.

Nikhyl Singhal

VP of Product at Facebook

Tell me something you did that worked out, but not for the reason that you thought it would work.

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?

Ayo Omojola

Chief Product Officer at Carbon Health

Tell me about something you have learned about yourself that reveal the limitation in how they work.

It's a way to test introspection, and once 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.

Scott Belsky

Chief Strategy Officer at Adobe

Do you consider yourself lucky?

I think it's a fascinating question, because some people who are super-insecure about where they are and how they got there and might decline admitting luck. 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 I just think that that's always an interesting conversation.

Scott Belsky

Chief Strategy Officer at Adobe

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.

Lauryn Isford

Head of Growth at Notion

What feedback will I be giving this person in their first performance review?

I have to do referral calls. You're interviewing someone, you want to give them the job, and they've got referees. Of course, the referees they have are the best people that they ever worked with and their favorite managers.

It's an amazing question, because the person can't dodge it. There's an answer, and it's incredibly enlightening.

Paul Adams

Chief Product Officer at Intercom

There are no rows in this table

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Lenny's People