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Q: What is your favorite interview question?

In most hiring processes, you’re lucky if you get 45 minutes to chat with a candidate before you have to make a thumbs-up or thumbs-down decision. How do you use that precious time to get the most—and most important—information?

For over a year now, I’ve been asking my illustrious podcast guests to share their favorite interview questions (nearly 150 guests now!), and the collection of questions that’s emerged is like nothing I’ve seen elsewhere. These are not just great questions—they are exceptionally good at pulling out the essential insights about the candidate in the least amount of time.

Below, I’ll share my 25 favorite high-signal-to-noise interview questions, including what to look for in a great answer, grouped by theme. If you’ve found any other questions that are super-valuable in your interview experience, please share in the comments!

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Thank you to Jeremy Jerschina for encouraging me to write this post, Gün Karagöz for consolidating a lot of these questions for me, and all of my podcast guests for sharing such amazing questions!

As you read through this list, pick a few that resonate with your process and goals, and try them out in your next interview panel.

How do they handle the hard stuff?

You can learn the most about how a person operates, thinks, and collaborates by exploring times when things didn’t go as planned. If they get hired, you can guarantee they’ll face unexpected challenges, so you’ll want to know how they’ll handle these moments before they have to tackle them on your team.

1. Talk me through your biggest product flop. What happened and what did you do about it?

“I look for people being brutally honest about how bad it was and why it failed. The rest of the interview, they’re trying to tell you all the wonderful things they did and all the accomplishments they had. And so I think the rawer the answer in terms of how bad it was and why, the better.”

—Annie Pearl, corporate vice president at Microsoft, ex-CPO at Calendly

2. 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.”

—Geoff Charles, VP of product at Ramp

3. Tell me about a time you’ve been in a challenging or highly ambiguous situation, and how you navigated that ambiguity.

“This 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. So I ask a lot of behavioral questions around that.

I look for people who look for structure and a way forward through the ambiguity. Also, I look for people who seek help, seek inputs, versus ‘This is the way.’ ”

—Jiaona Zhang (JZ), head of product at Linktree, ex-SVP of product at Webflow

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4. Describe a time when you were part of a controversial product decision, and what you did.

“It’s really revealing, because if they can explain this conflict and understand why this problem was really important—and represent both sides such that you can understand why that conflict existed in the first place—and they can do it in this even-keeled way, where you realize that they can take on these different perspectives, you start to learn a lot about that person.”

—Yuhki Yamashita, CPO of Figma

5. Tell me about a time something went wrong. What happened and what did you do about it?

“The question gets at when the product failed, and when something about the team didn’t work, because that’s what happens when you’re doing this work. What are people’s mindset? I look at the way they talk about it and the way they relate to evaluating the situation. 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 and head of AI at Asana

6. What is the worst product that you’ve ever shipped?

“It tells me you have some humor, you’re humble, and you can point out when you’ve made a mistake. You’ve done enough to be able to confidently say, of course I’ve made a mistake. Because none of us are perfect. And you know how to spot those mistakes and you can learn from them.”

—Maggie Crowley, VP of product at Toast

7. Tell me about a time when you needed to disagree with your manager or fight for a position against higher leadership.

“You want to look for people who have backbone but can also disagree and commit. That’s what I’m normally looking for.”

—Ethan Evans, retired VP at Amazon

“It showcases a lot about your character and if you are willing to stand your ground and push up when you need to. What is that influential communication skill that you have?”

—Inbal Shani, CPO of GitHub

How do they think?

The strongest and most valuable candidates are people who are good at self-reflection and can approach problems differently. They break norms, they challenge assumptions, and they think from first principles. These questions can help you find lateral and “out-of-the-box” thinkers.

8. What’s something that everyone takes for granted that you think is hogwash?

“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...?’ 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?’ 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 Meta

9. What’s an unfair secret you’ve learned to improve a product team’s velocity and energy level?

“When I say ‘unfair’ or ‘secret,’ I mean not something that you read on Medium. I’m looking for what you learned, how you learned it, how it works, and how you apply it.”

—Noah Weiss, CPO at Slack

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

“I’m trying to tease out introspection. Are you a person who is reflective about the decisions you made, why they worked, and why they did not? And do you incorporate that into your model so you make different decisions?”

—Ayo Omojola, CPO of Carbon Health

11. What is an experiment you launched that had a very unexpected result? And what did you do after that?

“This reveals the deep, deep level of their thinking. If you should expect that result based on what they described, then they are not thinking deeply enough. They are not understanding the customer enough.”

—Hila Qu, growth advisor

How do they build, ship, and drive impact?

You’re likely asking questions along these lines already, but here are some clever ways to get to the juiciest bits...