Lenny's Newsletter · Product & Work
TIER 4 2024-02-27
*P.S. Don’t miss **[Lennybot](https://www.lennybot.com/)** (an AI chatbot trained on my newsletter posts, podcast interviews, and more), my **[PM recruiting service](https://www.lennysjobs.com/)** (helping you hire Sr. PMs and VPs), my **[swag store](https://lennyswag.com/)****(great gifts for your favorite PM, or yourself!), and* **[The Best of Lenny’s Newsletter](https://lennyswag.com/products/vol-1)** ***[book](https://lennyswag.com/products/vol-1)** (all proceeds going to charity).* > ## 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! [Leave a comment](https://www.lennysnewsletter.com/p/how-to-learn-the-most-about-a-candidate/comments) *Thank you to [Jeremy Jerschina](https://www.linkedin.com/in/jeremy-jerschina/) for encouraging me to write this post, [Gün Karagöz](https://medium.com/@GunKaragoz/essential-takeaways-from-lennys-podcast-interview-episode-exploring-effective-interview-questions-edfc0cd8eb56) 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](https://www.lennyspodcast.com/behind-the-scenes-of-calendlys-rapid-growth-annie-pearl-cpo/), 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](https://www.lennyspodcast.com/velocity-over-everything-how-ramp-became-the-fastest-growing-saas-startup-of-all-time-geoff-charl/), 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)](https://www.lennyspodcast.com/building-minimum-lovable-products-stories-from-wework-and-airbnb-and-thriving-as-a-pm-jiaona-zha/), head of product at Linktree, ex-SVP of product at Webflow [](https://www.tiktok.com/@lennyrachitsky/video/7253276672542199083) [@lennyrachitsky](https://www.tiktok.com/@lennyrachitsky)[Pause it and try before she reveals what she’s looking for! #productmanager #productmanagement #jobinterview #interviewquestions #interviewtips best job interview questions, job interview examples, product manager job interview, how to become a product manager, product manager jobs, product manager test](https://www.tiktok.com/@lennyrachitsky/video/7253276672542199083) Tiktok failed to load. Enable 3rd party cookies or use another browser #### 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](https://www.lennyspodcast.com/an-inside-look-at-how-figma-builds-product-yuhki-yamashita-cpo-of-figma/), 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](https://www.lennyspodcast.com/how-to-ask-the-right-questions-project-confidence-and-win-over-skeptics-paige-costello-asana-i/), 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](https://www.lennyspodcast.com/mastering-product-strategy-and-growing-as-a-pm-maggie-crowley-toast-drift-tripadvisor/), 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](https://www.lennyspodcast.com/taking-control-of-your-career-ethan-evans-amazon/), 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](https://www.lennyspodcast.com/the-future-of-ai-in-software-development-inbal-shani-cpo-of-github/), 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](https://www.lennysnewsletter.com/p/first-principles-thinking). 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](https://www.lennyspodcast.com/building-a-long-and-meaningful-career-nikhyl-singhal-meta-google/), VP of product at Meta [Watch on YouTube](https://www.youtube.com/watch?v=o0Kq8QEijO4) #### 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](https://www.lennyspodcast.com/the-10-traits-of-great-pms-how-ai-will-impact-your-product-and-slacks-product-development-process/), 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](https://www.lennyspodcast.com/frameworks-for-product-differentiation-team-building-and-thinking-from-first-principles-ayo-omoj/), 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](https://www.lennyspodcast.com/the-ultimate-guide-to-adding-a-plg-motion-hila-qu-reforge-gitlab/), 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. #### 12. Tell me about your most significant professional accomplishment. > “To understand everything from the situation to the result, and everything they did in between, who they influenced, how they’d influenced, what decisions they had to make, what roadblocks they encountered.” > > —[Bill Carr](https://www.lennyspodcast.com/unpacking-amazons-unique-ways-of-working-bill-carr-author-of-working-backwards/), ex-Amazon VP, author of *Working Backwards* #### 13. Ask them about a product they shipped or a release they led that is not cherry-picked by the person. > “This helps you learn more about their frameworks, not just their outcomes—how they build products, how they know if they’re going to succeed, and how they approach building.” > > —[Laura Schaffer](https://www.lennyspodcast.com/career-frameworks-ab-testing-mistakes-counterintuitive-onboarding-tips-selling-to-developers-l/), VP of growth at Amplitude #### 14. What’s something that would not exist without your initiative? > “The ability to actually define something specific and tangible in itself is a really, really, really good sign. I think a lot of people definitely get startled by that question sometimes, because it requires you to know what it is you put on the table.” > > —[Upasna Gautam](https://www.lennyspodcast.com/an-inside-look-at-how-cnn-builds-product-upasna-gautam/), Sr. PM at CNN #### **15. Tell me about a time when 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](https://www.lennyspodcast.com/mastering-onboarding-lauryn-isford-head-of-growth-at-airtable/), head of growth at Notion #### **16. 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 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.’ 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](https://www.lennyspodcast.com/videos/an-inside-look-at-how-figma-builds-product-yuhki-yamashita-cpo-of-figma/), CPO of Figma [lennyspodcast](https://instagram.com/lennyspodcast) [](https://instagram.com/p/CtXwoCLp0-v) A post shared by [@lennyspodcast](https://instagram.com/lennyspodcast) #### **17. Tell me about a piece of work that you’re most proud of.** > “The reason I ask that is because 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](https://www.lennyspodcast.com/building-beautiful-products-with-stripes-head-of-design-katie-dill-stripe-airbnb-lyft/), head of design at Stripe > > “It gives you a little bit of indication what the person values and how they think about things.” > > —[Karri Saarinen](https://www.lennyspodcast.com/inside-linear-building-with-taste-craft-and-focus-karri-saarinen-co-founder-designer-ceo/), CEO of Linear [Watch on YouTube](https://www.youtube.com/watch?v=UhASMW6X4AY) ### Who are they as people? You’re hiring a whole human to work with all the other humans at your company. To get a sense of how that dynamic will or won’t work, you want to understand the person deeply. What are their strengths? What do they value? Where do they want to go in their career? #### **18. When I ask people you’ve worked with about you, what will I hear? What would they say are your superpowers and weaknesses?** > “I like this for a couple of reasons, not least of which is I often do follow up with references, and I like to triangulate their awareness of how other people calibrate them. Also, I like how they respond to criticism. Sometimes candidates surprise me. They say, hey, you’ll hear this critique a lot about me, I don’t think it’s fair. That can be an okay answer, but they’ve gotta be pretty robust there. > > Or it’s like, hey, this is something I’m working on. > > But I also like to hear what they think the superpowers are. Too often, a lot of attention in interviews is paid to weaknesses, which I care about, because I want to know what the downside is. But way more important to me is, what are you awesome at? What is the thing that I can just hitch a wagon to and ride? That’s what I want to know. Where’s the superpower that you’re crushing? > > What’s funny is that people are rarely, given my reference checks, accurate about what the critiques are, but they are usually pretty accurate about what their strengths are.” > > —[Andrew Bosworth](https://www.linkedin.com/in/andrew-bosworth-8247a01/), CTO at Meta #### **19. 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 if people have really gone back and reflected on why they are where they are today, that really says a lot about how they think about the world.” > > —[Eeke de Milliano](https://www.lennyspodcast.com/how-to-foster-innovation-and-big-thinking-eeke-de-milliano-retool-stripe/), ex-Retool, Stripe, co-founder of Constellate [Watch on YouTube](https://www.youtube.com/watch?v=Hneuz4rHSgc) #### **20. Tell me about something you’re really proud of that you accomplished. Take me through the process, and talk to me about why you’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](https://www.lennyspodcast.com/monetizing-passions-scaling-marketplaces-and-stories-from-a-creator-economy-vet-camille-hearst/), head of fan monetization at Spotify #### 21. Fast-forward three years. What’s different about you then? > “A lot of people will default to telling you about where they aspire to be in terms of role or title. I’m really looking for signals of humility, of self-awareness around areas of personal and professional growth; people who can be open about where they think they need work to grow themselves as people.” > > —[Ben Williams](https://www.lennyspodcast.com/how-snyk-built-a-product-led-growth-juggernaut-ben-williams-vp-of-product-at-snyk/), product and growth advisor [lennyspodcast](https://instagram.com/lennyspodcast) [](https://instagram.com/p/CsXcodXgYOL) A post shared by [@lennyspodcast](https://instagram.com/lennyspodcast) #### **22. Imagine you had a really great day at work and you’re telling your partner all about it. What are you telling them?** > “I’m trying to figure out if, left to their own devices, what do they go to naturally because it rewards them? Because I think it’s really important to find the highest, best use of everyone you hire. And sometimes you can get to the bottom of what’s the highest, best use if you understand where there’s a natural reward mechanism.” > > —[Tom Conrad](https://www.lennyspodcast.com/billion-dollar-failures-and-billion-dollar-success-tom-conrad-quibi-pandora-petscom-snap-ze/), CEO of Zero #### 23. What frustrates you the most about where you’re working right now? > “This is as people always tell you why they want to join Wise, or join whatever company you’re coming to, and that’s not that interesting. But what’s interesting is what they’re running away from. And usually there’s something broken there, that’s really wound them up. But what’s more interesting is they’ve been unable to fix it. And so, in asking this question and probing, you 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? And you think, ‘Okay, you’re going to run into that here every day, every week. Or ... you should be fine.’ And that’s why I ask that question.” > > —[Nilan Peiris](https://www.lennyspodcast.com/how-to-drive-word-of-mouth-nilan-peiris-cpo-of-wise/#transcript), CPO of Wise ### Other unexpected questions to consider #### **24. A group of scientists have invented a teleportation device. They’ve hired you to be their business counterpart and bring this to market. What two questions do you ask those scientists?** > “It’s a very simple question, and it’s a coded [Eigenquestion](https://coda.io/@shishir/eigenquestions-the-art-of-framing-problems/eigenquestions-3) test. Interestingly, all of a sudden the sharp product managers, engineers—basically every role—very quickly find what are the one or two Eigenquestions on this topic. Two questions can get to the heart of the problem.**”** > > **—**[Shishir Mehrotra](https://www.lennyspodcast.com/the-rituals-of-great-teams-shishir-mehrotra-coda-youtube-microsoft/), co-founder and CEO of Coda [](https://www.tiktok.com/@lennyrachitsky/video/7133654527420468526) [@lennyrachitsky](https://www.tiktok.com/@lennyrachitsky)[Pause and try! Are you getting the job at google? #google #founder #tech #productmanagement #startup #vctok #vc #softwareengineer](https://www.tiktok.com/@lennyrachitsky/video/7133654527420468526) Tiktok failed to load. Enable 3rd party cookies or use another browser #### 25. What question should I have asked you? > “I’ve been using that one forever, whether I am interviewing somebody or being interviewed, because the person is an expert in themselves. And if you say, ‘What question should I have asked you?’ a lot of times they’ll be like, ‘Oof.’ They’ll be knocked off base and then they’ll give you a really honest answer.” > > —[Christina Wodtke](https://www.lennyspodcast.com/the-ultimate-guide-to-okrs-christina-wodtke-stanford/), Stanford University professor If you’ve found any of these questions particularly interesting, or have your own ideas to share, leave a comment and share with other readers! [Leave a comment](https://www.lennysnewsletter.com/p/how-to-learn-the-most-about-a-candidate/comments) ### 📚 Further study 1. [How to pass any first-round interview (even in a terrible talent market)](https://www.lennysnewsletter.com/p/how-to-pass-any-first-round-interview) 2. [Adding a work trial to your interview process](https://www.lennysnewsletter.com/p/adding-a-work-trial-to-your-interview) 3. [Preparing for a PM interview](https://www.lennysnewsletter.com/p/preparing-for-a-pm-interview) 4. [My favorite PM interview questions](https://www.lennysnewsletter.com/p/my-favorite-pm-interview-questions) 5. [How to interview product managers](https://www.lennysnewsletter.com/p/how-to-interview-product-managers) 6. [Podcast episode: My favorite interview questions from 100+ guests](https://www.lennysnewsletter.com/p/my-favorite-interview-questions-from) *Have a fulfilling and productive week 🙏* ### **🔥 Featured open role: PM, Projects @ Notion** We recently partnered with Notion to help them scale their PM team. [One role that’s particularly interesting to me](https://boards.greenhouse.io/notion/jobs/5841932003) is an opportunity to own the end-to-end Project Management experience within Notion. If you’d like to get referred directly for this role, follow this button: [Apply to Notion](https://lennys-jobs.pallet.com/onboard/v3/0153c44c-b8c4-44b6-ba42-78fbcf220033/get-referred) *If you’re hiring and want to work with us, [apply here](https://airtable.com/apprGaxWWPYU0068E/shr2WFo5UqJjA5dQ8). Our team will reach out if we think it’s a good fit. Note, we primarily work with fast-growing U.S.-based startups.* **If you’re finding this newsletter valuable, share it with a friend, and consider subscribing if you haven’t already. There are [group discounts](https://www.lennysnewsletter.com/subscribe?group=true), [gift options](https://www.lennysnewsletter.com/subscribe?gift=true), and [referral bonuses](https://www.lennysnewsletter.com/leaderboard) available.** Sincerely, Lenny 👋