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Q: What is your favorite interview question?
In most hiring processes, youâre 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 mostâand most importantâinformation?
For over a year now, Iâve been asking my illustrious podcast guests to share their favorite interview questions (nearly 150 guests now!), and the collection of questions thatâs emerged is like nothing Iâve seen elsewhere. These are not just great questionsâthey are exceptionally good at pulling out the essential insights about the candidate in the least amount of time.
Below, Iâll share my 25 favorite high-signal-to-noise interview questions, including what to look for in a great answer, grouped by theme. If youâve found any other questions that are super-valuable in your interview experience, please share in the comments!
Thank you to Jeremy Jerschina for encouraging me to write this post, GĂŒn 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.
You can learn the most about how a person operates, thinks, and collaborates by exploring times when things didnât go as planned. If they get hired, you can guarantee theyâll face unexpected challenges, so youâll want to know how theyâll handle these moments before they have to tackle them on your team.
âI look for people being brutally honest about how bad it was and why it failed. The rest of the interview, theyâre 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.â
âAnnie Pearl, corporate vice president at Microsoft, ex-CPO at Calendly
âI 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.â
âGeoff Charles, VP of product at Ramp
âThis is a big one for me because, at the end of the day, the PM job is really ambiguous. Itâs really hard to describe on a piece of paper all the things that youâre 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 âThis is the way.â â
âJiaona Zhang (JZ), head of product at Linktree, ex-SVP of product at Webflow
âItâs really revealing, because if they can explain this conflict and understand why this problem was really importantâand represent both sides such that you can understand why that conflict existed in the first placeâand 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.â
âYuhki Yamashita, CPO of Figma
âThe question gets at when the product failed, and when something about the team didnât work, because thatâs what happens when youâre doing this work. What are peopleâs 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.â
âPaige Costello, co-head of product management and head of AI at Asana
âIt tells me you have some humor, youâre humble, and you can point out when youâve made a mistake. Youâve done enough to be able to confidently say, of course Iâve made a mistake. Because none of us are perfect. And you know how to spot those mistakes and you can learn from them.â
âMaggie Crowley, VP of product at Toast
âYou want to look for people who have backbone but can also disagree and commit. Thatâs what Iâm normally looking for.â
âEthan Evans, retired VP at Amazon
âIt 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?â
âInbal Shani, CPO of GitHub
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 âout-of-the-boxâ thinkers.
âIâm 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 werenât genuine.
Thereâs no way to answer that question without being genuinely opinionated. Because it starts with âWhat is the thing that you think…?â When I break that wall, Iâm testing: is this person authentic? Because sometimes Iâm dismissing them because they told me nothing new. But I donât want the interview process to penalize them, and this was my âsaveâ question.
Sometimes Iâll ask a manager, âLook, youâve managed hundreds of people in your career. Whatâs conventional wisdom that you bet against, that you have found is actually inaccurate?â You could do that for âWhat do people think about AI thatâs inaccurate, that everyone believes?â You could do that for domains. You can do all kinds of things.â
âNikhyl Singhal, VP of product at Meta
âWhen I say âunfairâ or âsecret,â I mean not something that you read on Medium. Iâm looking for what you learned, how you learned it, how it works, and how you apply it.â
âNoah Weiss, CPO at Slack
âIâm 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?â
âAyo Omojola, CPO of Carbon Health
âThis 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.â
âHila Qu, growth advisor
Youâre likely asking questions along these lines already, but here are some clever ways to get to the juiciest bits.