| Date | Guest | Interview Question |
| 12-Sep-24 | Phyl Terry | Tell me about a time that you, the company, brought in a senior level person and it failed, and why? |
| 12-Sep-24 | Phyl Terry | If you want to get references, what you do is you want to leave a voicemail or you could send an email, whatever. And you want to say, "I'm about to hire Lenny. If it would be a huge mistake if I didn't bring him on, if you think he's amazing, then call me back. Otherwise, don't bother." |
| 16-Jun-24 | Tanguy Crusson | 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?" |
| 26-May-24 | Bangaly Kaba | I go through and I think about what are the four, usually five skills that are really critical for someone to have in this job ... then I ask them, I say, Hey, take out a piece of paper or take out your laptop. I'm going to give you five skills and I want you to stack-rank them for me. One to five. So one being the one you're strongest at and five being the one you're relatively weakest at. |
| 12-May-24 | Vikrama Dhiman | What I like to do with them is to brainstorm choices on an actual product. |
| 28-Apr-24 | Kayvon Beykpour | 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. |
| 21-Apr-24 | Mihika Kapoor | I like to ask people what motivates them. |
| 18-Apr-24 | Dalton Caldwell | "Tell me about what you're working on." Or, "What have you learned since you started?" |
| 14-Apr-24 | David DeSanto | I won't say there's a specific question. It's so much a method. So I really like the star method for asking questions. |
| 07-Apr-24 | Claire Vo | I like to ask candidates how they would improve our business model. |
| 24-Mar-24 | Kunal Shah | 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 military? What happens to stock market? What happens to order of things? |
| 21-Mar-24 | Emilie Gerber | If a client comes to you and they're convinced they have something that's press worthy, like an announcement that they think should be in the Wall Street Journal or something, and you know for a fact that it isn't, what steps do you take? What do you do next? |
| 17-Mar-24 | Noam Lovinsky | I generally like interview questions that allow us to kind of do some work together ... "Let's work a product problem together." It could be anything from like, "Let's design an alarm clock for children." Or lately I've been using one. "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. |
| 10-Mar-24 | Marty Cagan | Can you define the job of a product manager? |
| 03-Mar-24 | Andrew ‘Boz’ Bosworth | People you've worked with, what would they say are your greatest strengths and weaknesses? |
| 25-Feb-24 | Donna Lichaw | Imagine it's a few years out and you've had the best however long, year or three years of your life, what would you be telling me? |
| 22-Feb-24 | Elizabeth Stone | I often ask people what would their priorities be, what would they do differently if they had my job. |
| 18-Feb-24 | Jason Lemkin | What do you want to do your first fourteen days? |
| 08-Feb-24 | Logan Kilpatrick | I'm always curious to hear what people's... The thing that they so strongly believe that people disagree with them on. |
| 04-Feb-24 | Megan Cook | I love to ask people about their biggest failure. |
| 21-Jan-24 | Richard Rumelt | What have you done that was difficult and that you're proud of? |
| 21-Jan-24 | Richard Rumelt | What do you think was an interesting strategy from any time in the past you want to call out? |
| 21-Jan-24 | Richard Rumelt | Depending on the person's background, I might ask them about a particular company or situation, let's say, why do you think this worked or why didn't it work? |
| 18-Jan-24 | Heidi Helfand | 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? |
| 11-Jan-24 | Sam Schillace | How many zeros are at the end of 100 factorial? |
| 07-Jan-24 | Will Larson | Hey, we've really loved you. You're going to come through. I think you're going to get a lot of offers from other companies too. I bet you'll have three or four really compelling offers because you're a fantastic candidate. How are you going to figure out really specifically which of those options are right for you? |
| 04-Jan-24 | Judd Antin | 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. |
| 29-Dec-23 | Nir Eyal | I'm a huge fan of small projects. So, what I'll oftentimes do is pay people to do a small project and then I can see their work output. I find that that works much, much better than any question I can come up with. |
| 27-Dec-23 | Sarah Tavel | I always love hearing the journey people take and specifically how they've made decisions along the way, what drives them from each step. I think that's always very illuminating. |
| 21-Dec-23 | Christian Idiodi | I always give them a problem to solve. That is probably my favorite question, and it's not a traditional problem. I probably will say something like, 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, will not solve the problem. And I would love to give that problem to you. Walk me through how you go about tackling this or solving this. |
| 17-Dec-23 | Jason Fried | If you had more time, what would you do with this idea. |
| 17-Dec-23 | Jason Fried | Whose work do you admire? Why? |
| 15-Dec-23 | Matthew Dicks | How did you get into the job you currently have? |
| 10-Dec-23 | Kim Scott | Tell me the story of your career. |
| 07-Dec-23 | Anuj Rathi | Which are the products where you decide speed is more important versus which are the products where you have decide excellence is more important? |
| 03-Dec-23 | Ebi Atawodi | What is your leadership philosophy? |
| 03-Dec-23 | Ebi Atawodi | Tell me your favourite product and why? If you could improve it, what would you do? |
| 01-Dec-23 | Inbal Shani | What is the most innovative thing you have done? Why is it innovative? |
| 01-Dec-23 | Inbal Shani | Give me an example of a time when you had a disagreement with your manager and how did you handle it? |
| 26-Nov-23 | Tom Conrad | Tell me about a time in your career when |
| 26-Nov-23 | Tom Conrad | Imagine you have a great day at work. Tell me what you did on that day? |
| 19-Nov-23 | Paul Millerd | What makes you come alive? |
| 16-Nov-23 | Melissa Perri and Denise Tilles | When was the last time you changed your mind about something really important and why? |
| 16-Nov-23 | Melissa Perri and Denise Tilles | Tell me about the time when you failed and what happened? |
| 09-Nov-23 | Ramesh Johari | Imagine all your plans and dreams work out. What you imagine the impact is? Who is impacted? |
| 05-Nov-23 | Maggie Crowley | What is the worst product you've ever shipped? |
| 02-Nov-23 | Bill Carr | Tell me about your most significant professional accomplishment? |
| 29-Oct-23 | Eric Ries | Describe a best practice you've learned in your career? Tell me a situation in which this best practice wouldn't work or be the right thing to do? |
| 22-Oct-23 | April Dunford | Think of something you've bought recently and write me two paragraphs and sell me on it. |
| 19-Oct-23 | Gina Gotthilf | Why do you want to work here? |
| 19-Oct-23 | Gina Gotthilf | What are you world class at? How do you know? |
| 15-Oct-23 | Katie Dill | Tell me about the work you're most proud of? |
| 08-Oct-23 | Karri Saarinen | What are you the most proud of and why? |
| 05-Oct-23 | Brian Balfour | Breaking down their previous work / problems. |
| 01-Oct-23 | Lane Shackleton | Teach me something that I already don't know. |
| 28-Sep-23 | Maya Prohovnik | If you could make a podcast about anything, what would it be? |
| 24-Sep-23 | Nilan Peiris | What is it that most frustrates you about where you're working in right now? |
| 21-Sep-23 | Itamar Gilad | Design something for a niche audience? E.g. Navigation system for elderly, Laptop for vision impaired people |
| 17-Sep-23 | Christopher Lochhead | Is there anything else? |
| 17-Sep-23 | Christopher Lochhead | Are you legendary? |
| 14-Sep-23 | Oji Udezue | Ask people to introduce themselves. |
| 14-Sep-23 | Oji Udezue | Ask people about what they think they are really good at? What do they need to learn? |
| 03-Sep-23 | Tim Holley | Case Study Question |
| 03-Sep-23 | Tim Holley | Tell me something you've taught yourself? |
| 27-Aug-23 | Meltem Kuran Berkowitz | What would your siblings say about you? |
| 24-Aug-23 | Bob Moesta | What are the top 3 things you struggle with in your business today that if you solved could fundamentally change the business? |
| 20-Aug-23 | Camille Hearst | Tell me about something you're really proud of? |
| 13-Aug-23 | Austin Hay | Tell me about the most difficult/challenging thing you've had to overcome in your life? |
| 10-Aug-23 | Christopher Miller | Case Study Question |
| 06-Aug-23 | Geoff Charles | What's the hardest thing you've ever done? |
| 30-Jul-23 | Nicole Forsgren | Question about hard decisions that they had to make. |
| 27-Jul-23 | Ronny Kohavi | Tell me what the static qualifier does for a variable/function? |
| 23-Jul-23 | Noah Weiss | What unfair secrets have you learned to improve velocity or energy levels of your team? |
| 16-Jul-23 | Hari Srinivasan | What's the most complex thing you've ever built? |
| 13-Jul-23 | Julia Schottenstein | When was the last time you had to learn something new and how did you do it? |
| 09-Jul-23 | Paige Costello | Tell me about a situation when things went wrong. |
| 02-Jul-23 | Jiaona Zhang | Tell me about an challenging and ambiguous situation and how did you deal with it? |
| 25-Jun-23 | Sri Batchu | What's something you're really bad at that you still do and why? |
| 15-Jun-23 | Luc Levesque | Teach me something about growth that I don't already know. |
| 11-Jun-23 | Nikhyl Singhal | What's something everyone takes for granted that you think is inaccurate? |
| 04-Jun-23 | Jeremy Henrickson | What question do you have for me? |
| 21-May-23 | Gustav's derstr m | What's the meaning of it all? |
| 18-May-23 | Scott Belsky | What have you learned about yourself? |
| 18-May-23 | Scott Belsky | Do you consider yourself lucky? |
| 14-May-23 | Ayo Omojola | Tell me something you did that worked out but not for the reason you thought it would work? |
| 14-May-23 | Ayo Omojola | Tell me something you did that was a good decision that didn't work? |
| 04-May-23 | David Singleton | Which leader that they've worked for do they admire the most and why? |
| 30-Apr-23 | Carilu Dietrich | How many people have you fired and tell me about each of these experiences. |
| 20-Apr-23 | Varun Parmar | Math problem based on how Adobe created its Adobe Creative Suite Bundle Pricing. |
| 16-Apr-23 | Ada Chen Rekhi | What's a common misconception people have about you? |
| 13-Apr-23 | Laura Modi | Teach me something. |
| 09-Apr-23 | Shweta Shrivastava | When was one time that you failed and what did you learn from it? |
| 06-Apr-23 | Nikita Miller | We think about product in the context of artist, scientist, general manager. Where do you spike? |
| 02-Apr-23 | Hila Qu | What is an experiment you launched that had a very unexpected result and what did you do after? |
| 23-Mar-23 | Lulu Cheng Meservey | What have you been reading? |
| 19-Mar-23 | Josh Miller | What would you like to ask me? |
| 16-Mar-23 | Christina Wodtke | What question should I have asked you? |
| 02-Mar-23 | Gustaf Alstr mer | What have you done since you applied at YC? |
| 26-Feb-23 | Annie Pearl | Talk me through your biggest flop? What happened and what did you do about it? |
| 23-Feb-23 | Upasna Gautam | What's something that would not exist without your initiative? |
| 19-Feb-23 | Patrick Campbell | If someone in slack responded to a message with something indirectly offensive, what would you do? What do you think the company should do? |
| 16-Feb-23 | Christine Itwaru | If you could choose any career other than what you're doing, what would it be and why? |
| 05-Feb-23 | Marily Nika | How would you explain what a database is to a 5 year old? |
| 02-Feb-23 | Eeke de Milliano | To what do you attribute your success? And you can't say luck. |
| 29-Jan-23 | Zoelle Egner | Solve an unfamiliar problem using Zappier. |
| 26-Jan-23 | Vijay Iyengar | Walk me through the story of you from college to now. |
| 19-Jan-23 | Ravi Mehta | Tell me about a product that you love? |
| 15-Jan-23 | John Cutler | So one that I like to do is, I do the behavioral questions like, "Tell me about stuff," but then I'll ask them like, "Imagine I'm interviewing a person you worked with. Now answer in there, tell me about of the same situation." |
| 05-Jan-23 | Jules Walter | What's something work related that you're trying to get better about? |
| 11-Dec-22 | Camille Ricketts | What is one thing that you think that led to your success that nobody else in your peer set has done? What was something that you did on a lark or that you were like, this is a big bet, or this isn't probably going to work, or it's a mistake that it even turned out this way, but it ended up being great. What is that one thing that was unusually conceived that you want to share with people? |
| 27-Nov-22 | Petra Wille | Tell me about the last time when you did user interviews. |
| 20-Nov-22 | Ian McAllister | At this stage in your career, what have you learned about yourself? How are you different? |
| 06-Nov-22 | Ben Williams | Fast forward three years, what's different about you? |
| 06-Nov-22 | Ben Williams | Tell me about DEI initiatives you've personally been involved in. |
| 03-Nov-22 | Lauren Ipsen | Good strengths and weaknesses question |
| 02-Oct-22 | Kristen Berman | What is a personality trait that defines you? |
| 18-Sep-22 | Jason Shah | What is a risk you regret not taking, why, and what did you learn about yourself? |
| 11-Sep-22 | Emily Kramer | The company that you're working on, what's the product? Why is it better? Who is it for? |
| 11-Sep-22 | Emily Kramer | Describe something complicated that you know well that others don't and describe it as simply as you can. |
| 11-Sep-22 | Emily Kramer | Walk me through a project you've done recently from start to finish. Can you tell me the goal? And can you tell the audience? |
| 04-Sep-22 | Ryan J. Salva | Teach me something new in one minute. |
| 18-Aug-22 | Arielle Jackson | Tell me about a project you're proud of. |
| 18-Aug-22 | Arielle Jackson | Tell me about a campaign you recently come across that you were not involved with that you thought was cool. |
| 14-Aug-22 | Shishir Mehrotra | Design a one-page dashboard for a product. |
| 24-Jul-22 | Ken Norton | How does the company define a product team? |
| 24-Jul-22 | Ken Norton | Discuss an example of something they've shipped recently. |
| 05-Jul-22 | Sanchan Saxena | Tell me the story of your career and focus more on why you did what you did. |
| 16-Jun-22 | Jackie Bavaro | Tell me about a recent project that you're proud of. |
| 13-Jun-22 | Gokul Rajaram | What are you most proud of? |