My favorite interview questions from 100+ guests
Summary
This episode compiles 17 favorite interview questions from over 100 guests of Lenny’s Podcast, focusing on the lightning round segment where guests share their go-to questions for evaluating candidates. The questions are curated to help listeners prepare for interviews, whether they are hiring managers looking to refine their process or candidates anticipating tough questions.
Each question is presented with context from the guest who recommended it, explaining what they look for in a response. The questions range from assessing self-awareness and curiosity (“To what do you attribute your success? And you can’t say luck.”) to evaluating problem-solving under constraints (the teleportation device eigenquestion test). Other themes include understanding how candidates handle ambiguity, failure, and personal growth.
The compilation includes insights from product leaders at companies like Retool, Ramp, Coda, Figma, Stripe, Linear, Spotify, Webflow, Slack, and Adobe. The episode concludes with a piece of advice on conducting reference calls, framing the question around what feedback the referee would give in the candidate’s first performance review.
Recommendations
Tools
- Sendbird — An all-in-one communications API platform for web and mobile, featuring AI-powered chatbots, chat, video calls, and live streaming. Mentioned as a sponsor, it’s used by companies like Hinge and Patreon for in-app communication.
- Eppo — A next-generation A/B testing and feature management platform built by alums of Airbnb and Snowflake. Used by companies like Twitch and Miro to power experiments and increase experimentation velocity. Mentioned as a sponsor.
Topic Timeline
- 00:00:00 — Introduction to the lightning round interview questions compilation — Lenny introduces the episode, explaining it is a special compilation of his favorite interview questions from the lightning round segment of his podcast. He has selected 17 questions from over 100 guests. The episode is intended for anyone preparing to interview candidates, improving their interview questions, or getting ready to be interviewed themselves.
- 00:03:22 — Eka DeMigliano’s question on attributing success — The first question is from Eka DeMigliano, former head of product at Retool and PM at Stripe. She asks, “To what do you attribute your success? And you can’t say luck.” She explains this reveals a candidate’s self-awareness and curiosity, showing how they reflect on their journey and think about the world.
- 00:04:02 — Jeff Charles on the hardest thing ever done — Jeff Charles, head of product at Ramp, shares his question: “What’s the hardest thing you’ve ever done?” He asks this because working at Ramp is hard, and he wants to understand what difficulty means to the candidate, why it was hard, how they overcame it, and their agency in the process.
- 00:04:36 — Shashir Marotra’s teleportation device eigenquestion test — Shashir Marotra, CEO and co-founder of Coda, presents a hypothetical question about bringing a teleportation device to market. The candidate can only ask two questions of the reclusive scientists. This tests their ability to identify the fundamental eigenquestions that drive decision-making, such as safety for humans and cost structure (CapEx vs. OpEx).
- 00:08:45 — Yuki Yamashita on controversial product decisions — Yuki Yamashita, chief product officer at Figma, recommends asking candidates to describe a time they were part of a controversial product decision. This reveals their ability to set up conflict, understand why a problem is important, represent multiple perspectives evenly, and demonstrate storytelling skills that compel others to care about the problem.
- 00:10:03 — Katie Dill, Kari Saarinen, and Camille Hurst on pride in work — Katie Dill (head of design at Stripe), Kari Saarinen (CEO of Linear), and Camille Hurst (product leader at Spotify) all share the question: “Tell me what work you are most proud of.” This helps understand a candidate’s taste, judgment, motivation, what they value, and what good outcomes look like to them. It’s a positive way to explore their work ethic and what they care about.
- 00:11:29 — Jay-Z on navigating ambiguity — Jay-Z, head of product at Webflow, prefers behavioral questions about challenging or ambiguous situations. She looks for candidates who can put structure and a path forward through ambiguity, seek help and inputs, and define milestones to gauge if their approach is working. This reflects the inherently ambiguous nature of product management.
- 00:12:48 — Noah Weiss on unfair secrets for velocity and energy — Noah Weiss, chief product officer at Slack, asks: “What unfair secrets have you learned to improve the velocity and energy level of a product team?” He seeks insights not found on Medium, wanting to understand how the candidate learned and applies these unique tactics, which also provides interesting bits of inspiration.
- 00:13:15 — Ben Williams on future self and curiosity — Ben Williams, former VP of product at Snyk, asks: “Fast forward three years. What’s different about you?” He looks for humility and self-awareness about areas for personal and professional growth, not just role aspirations. He also emphasizes looking for curiosity throughout the interview, akin to a child constantly asking why.
- 00:14:42 — Meltem Koran Berkowitz on sibling or parent perspective — Meltem Koran Berkowitz, head of growth at an early-stage company, asks: “What would your siblings say about you?” (or parents if no siblings). This reveals the candidate’s self-awareness and sincerity about how others perceive them, looking for humble, genuine answers rather than idealized, boastful ones.
- 00:15:36 — Paige Costello on when something went wrong — Paige Costello, co-head of product management and head of AI at Asana, asks: “Tell me about a time something went wrong.” She wants to understand the candidate’s mindset, how they relate to and evaluate failure, and their approach when things aren’t working. This reveals a lot about their thought process and self-perception in difficult situations.
- 00:16:22 — Nikhil Singhal on conventional wisdom hogwash — Nikhil Singhal, VP of product at Facebook, asks: “What’s something that everyone takes for granted that you think is essentially hogwash or inaccurate?” This question breaks the interview mindset, forcing genuine, opinionated answers. It tests authenticity and helps avoid dismissing high-quality candidates who might otherwise give rehearsed responses.
- 00:18:01 — Ayo Omojalo on outcomes versus expectations — Ayo Omojalo, chief product officer at Carbon Health, asks: “Tell me something you did that worked out, but not for the reason that you thought it would work. Or tell me something you did that was a good decision that didn’t work.” This probes the candidate’s introspection and ability to reflect on decisions, learn from outcomes, and incorporate those lessons into future models.
- 00:18:30 — Scott Belsky on personal limitations and luck — Scott Belsky, chief strategy officer at Adobe, asks about something the candidate has learned about themselves that reveals a limitation in how they work, testing introspection and openness about struggles. He also likes the question, “Do you consider yourself lucky?” to gauge comfort with acknowledging privilege and luck in their career journey.
- 00:19:22 — Lauren Isford on defining impact — Lauren Isford, head of growth at Notion, asks: “Tell me about a time that you delivered something that was impactful.” She uses this to understand how the candidate defines impact and what it means to them. For growth roles, she looks for intrinsic motivation about impacting the business.
- 00:19:52 — Paul Adams on reference call advice — Paul Adams, chief product officer at Intercom, shares a killer question for reference calls: “What feedback will I be giving this person in their first performance review?” This question is hard to dodge and provides incredibly enlightening insights from referees who are typically the candidate’s biggest supporters.
Episode Info
- Podcast: Lenny’s Podcast: Product | Career | Growth
- Author: Lenny Rachitsky
- Category: Technology Business Entrepreneurship
- Published: 2023-11-29T12:01:00Z
- Duration: 00:20:45
References
- URL PocketCasts: https://pocketcasts.com/podcast/lennys-podcast-product-career-growth/aff3edd0-c8a4-013a-d954-0acc26574db2/my-favorite-interview-questions-from-100-guests/beb4d0d8-6db0-4e4b-ab6b-b137f31f5292
- Episode UUID: beb4d0d8-6db0-4e4b-ab6b-b137f31f5292
Podcast Info
- Name: Lenny’s Podcast: Product | Career | Growth
- Type: episodic
- Site: https://www.lennysnewsletter.com/podcast
- UUID: aff3edd0-c8a4-013a-d954-0acc26574db2
Transcript
[00:00:00] Welcome to a very special episode of the podcast.
[00:00:06] Ever since I started this podcast, one of people’s favorite segments continues to be
[00:00:10] the lightning round, and in particular, a question I ask guests around their favorite
[00:00:15] interview question that they like to ask candidates and what they look for in a good answer.
[00:00:20] What we’ve done is we’ve picked my favorite interview questions that guests have shared.
[00:00:25] Out of over 100 guests on the podcast, we’ve got 17 of my favorite interview questions
[00:00:30] all combined in this one episode.
[00:00:33] You can use this episode anytime you are preparing to interview candidates, if you want to improve
[00:00:39] your existing interview questions, or if you’re about to get interviewed and you want to prepare
[00:00:43] for the kinds of questions that you might get in the interview process.
[00:00:47] Before we dive in, let me tell you about a product called Sendbird, the all-in-one communications
[00:00:52] API platform designed for both web and mobile.
[00:00:55] In a world saturated with multi-channel communication, product teams are discovering
[00:01:00] the effectiveness of in-app communication.
[00:01:02] With Sendbird, businesses can elevate their in-app experience with decluttered and branded
[00:01:08] communication featuring AI-powered chatbots, one-way messages, chat, video calls, and live
[00:01:14] stream capabilities, all tailored for commerce, marketing, and top-tier support.
[00:01:18] Forward-thinking companies such as Hinge, Patreon, Yahoo, Accolade, and more use Sendbird
[00:01:24] to build in-app communication.
[00:01:25] In-app communication has the highest conversion, highest engagement, and highest satisfaction
[00:01:34] of any communication channel.
[00:01:36] And when it comes to investing in this channel, trust Sendbird to take your in-app communication
[00:01:41] experience to the next level.
[00:01:43] Start today with Sendbird’s free plan, and as a listener of Lenny’s podcast, you’ll get
[00:01:48] an additional two months of unlimited usage and access to all premium features, including
[00:01:53] creating your very own generative AI chatbot.
[00:01:55] Visit Sendbird.com slash Lenny to begin your free journey.
[00:02:01] That’s Sendbird.com slash Lenny.
[00:02:04] This episode is brought to you by Eppo.
[00:02:07] Eppo is a next-generation A-B testing and feature management platform built by alums
[00:02:12] of Airbnb and Snowflake for modern growth teams.
[00:02:15] Companies like Twitch, Miro, ClickUp, and DraftKings rely on Eppo to power their experiments.
[00:02:21] Experimentation is increasingly essential for driving growth and for understanding the
[00:02:25] performance of new features.
[00:02:27] And Eppo helps you increase experimentation velocity while unlocking rigorous, deep analysis
[00:02:32] in a way that no other commercial tool does.
[00:02:35] When I was at Airbnb, one of the things that I loved most was our experimentation platform,
[00:02:39] where I could set up experiments easily, troubleshoot issues, and analyze performance all on my
[00:02:43] own.
[00:02:44] Eppo does all that and more, with advanced statistical methods that can help you shave
[00:02:48] weeks off experiment time, an accessible UI for diving deeper into performance, and out-of-the-box
[00:02:53] reporting that helps you avoid the risk of a failure.
[00:02:55] Eppo is a next-generation A-B testing and feature management platform built by alums of
[00:02:55] Airbnb and Snowflake for modern growth teams.
[00:02:55] Eppo also makes it easy for you to share experiment insights with your team,
[00:03:01] sparking new ideas for the A-B testing flywheel.
[00:03:04] Eppo powers experimentation across every use case, including product, growth, machine learning,
[00:03:10] monetization, and email marketing.
[00:03:12] Check out Eppo at geteppo.com slash lenny and 10x your experiment velocity.
[00:03:18] That’s geteppo.com slash lenny.
[00:03:22] First up, we’ve got Eka DeMigliano.
[00:03:24] Eka was head of product at Retool.
[00:03:27] She was also a PM at Stripe.
[00:03:29] Currently, she’s actually starting her own company.
[00:03:31] And so here’s Eka sharing her favorite interview question.
[00:03:36] To what do you attribute your success?
[00:03:38] And you can’t say luck.
[00:03:40] Because, you know, I think humble people will always say luck in some way.
[00:03:44] And, you know, I always kind of wanted it like, did you like, how self-aware are you
[00:03:47] basically?
[00:03:48] And I think, and how curious are you?
[00:03:49] And I think people have really sort of gone back and reflected on
[00:03:52] why are they?
[00:03:54] Where they are today really, really says a lot about how they think about the world.
[00:03:58] Next up, we’ve got Jeff Charles, head of product at Ramp.
[00:04:02] And also just happens to be one of the most popular episodes of the podcast.
[00:04:05] I asked, what’s the hardest thing you’ve ever done?
[00:04:08] And I asked that because working at Ramp is hard.
[00:04:12] I want to understand like what hard means for them.
[00:04:14] I want to understand why it was hard.
[00:04:16] I want to understand how they overcame that difficulty, how they worked with other people
[00:04:19] to overcome that difficulty and how much agency they had in overcoming that.
[00:04:24] So it’s a really, it’s a really good sign around what is difficulty to them and how
[00:04:29] much work they put into overcoming that.
[00:04:31] Next up, we’ve got Shashir Marotra, CEO and co-founder of Coda.
[00:04:36] Funny enough, we posted this exact clip to TikTok and Instagram reels and it blew up.
[00:04:43] It’s one of the most popular clips we’ve ever put on our channels.
[00:04:46] By the way, did you know I have a TikTok and an Instagram channel?
[00:04:49] Just look up Lenny’s podcast on TikTok or Instagram.
[00:04:52] Anyway, with that, here’s Shashir Marotra.
[00:04:54] Sharing his favorite interview question.
[00:04:57] It’s a very simple question and it’s a coded eigenquestion test.
[00:05:01] And the question is, a group of scientists have invented a teleportation device.
[00:05:07] They’ve hired you, Lenny, to be their sort of business counterpart, bring this to market,
[00:05:13] product counterpart.
[00:05:14] This question actually worked well for anyone.
[00:05:16] Let’s say you could be a product manager for this thing, bring it to market.
[00:05:19] What do you do?
[00:05:20] That’s the whole question.
[00:05:21] People, usually people will start asking a bunch of questions.
[00:05:24] And say, well, tell me more about this device.
[00:05:26] Like, what does it do?
[00:05:27] How does it work?
[00:05:28] And, you know, is it, is it big?
[00:05:30] Is it small?
[00:05:30] Is it fast?
[00:05:31] Does it like, does it disintegrate things or not?
[00:05:34] Does it need a receiver and a sender?
[00:05:36] Does it, you know, is it safe?
[00:05:37] Like all these different questions come out.
[00:05:38] And at some point I’ll just let those questions come out.
[00:05:41] And at some point I’ll say, okay, a nice job generating all the questions.
[00:05:45] Turns out the scientists, they kind of hate talking to people.
[00:05:47] And they’re kind of annoyed by all your questions.
[00:05:50] And so they’ve decided that they will answer only two of your questions.
[00:05:54] Okay.
[00:05:54] And after that, they expect a plan.
[00:05:57] What two questions do you ask?
[00:05:59] And interestingly, all of a sudden, like the sharp, you know, product
[00:06:02] managers, engineers, so basically every role, they very quickly find what
[00:06:07] are the two, one or two eigen questions on this topic and there’s no right
[00:06:11] answer, but I’ll tell you, like one of my favorite ones as a product manager
[00:06:15] said, okay, if I had to ask two questions, the two questions I’d ask one is, is
[00:06:19] it safe enough for humans or not?
[00:06:21] And that was a, like a very like crisp way to get to.
[00:06:25] Like just safety, how reliable is it?
[00:06:27] He didn’t ask how reliable it is, how many bits in the middle is like, just
[00:06:29] tell me, is it safe enough for humans or not?
[00:06:31] And the second one is, is it more expensive CapEx or OpEx?
[00:06:34] Is it more expensive to buy them or to run them?
[00:06:36] And then he took those two questions and he said like, just with those two
[00:06:39] questions, I can form these quadrants and you can say, oh, it’s safe enough for
[00:06:43] humans and it’s cheaper to, they’re very cheap to buy, but expensive to run.
[00:06:48] Then you probably run them like human fax machines.
[00:06:50] Like you put them everywhere you can and you say, hey, look, it’s expensive to use.
[00:06:54] But like, you all have the ability to teleport anywhere you want.
[00:06:57] And this is, this is how we’re gonna run it.
[00:06:58] If the other hand, they’re very expensive to buy, but cheap to run, you probably
[00:07:04] have to place them very strategically.
[00:07:05] In which case, what do you probably do is replace airports.
[00:07:07] Cause like airports are pretty strategically placed in places where people are trying
[00:07:10] to, trying to get, get around places.
[00:07:12] If it’s not safe enough for humans, then you’ve got a whole different class of
[00:07:14] use cases where you go value what goods are transported in very costly ways.
[00:07:19] And, you know, people come up with like, you know, do you do the most expensive
[00:07:22] things or do you do the, like, you know, the, it is.
[00:07:24] Is, is teleporting, you know, people’s replacement hearts.
[00:07:28] Is that like a, like a really demanding thing?
[00:07:31] So, so, but these two questions kind of, kind of get to the, the, the heart of it.
[00:07:35] The question’s totally made up, like no teleportation device
[00:07:37] exists, at least not yet.
[00:07:39] And I find that people’s ability to learn the method is significantly
[00:07:44] higher if it’s low stakes, that question, by the way, if you ask a kid that
[00:07:47] question, the, you know, hey, new teleportation device, you know, you,
[00:07:50] you get to ask two questions, almost every kid will like quickly get to two
[00:07:54] pretty good eyeing questions.
[00:07:55] Again, kids are incredibly good at simplifying these things down.
[00:07:58] It’s actually a skill we like remove from ourselves.
[00:08:02] Like I’ll see all your candidates tell me things like, well, I guess I would
[00:08:04] ask them what, what size it is.
[00:08:06] And like, why would you ask them what size, what, what, what decision is that
[00:08:09] can allow you to make to, to know what size it is and, and, you know, sometimes
[00:08:13] they can explain it, sometimes not don’t get hired, but they, uh, but then actually
[00:08:17] the, the thing I’d say about it is there are eyeing questions kind of everywhere.
[00:08:20] I mean, it’s, you can, you can take any product out there.
[00:08:22] I’ll, I’ll do it with my kids a lot.
[00:08:23] And they’ll say.
[00:08:24] You know, uh, I was just riding with, with my younger daughter and she said,
[00:08:28] you know, how come there’s three gas stations, like in the same corner?
[00:08:32] Like, why, why, why do, why do people do that?
[00:08:34] Yeah.
[00:08:34] Uh, that’s a really, that’s a really insightful observation.
[00:08:37] What’s the eyeing question?
[00:08:38] How do you place a gas station?
[00:08:39] You can almost take anything and say, what is the question that
[00:08:42] really drives, drives this answer?
[00:08:45] This next interview question comes from Yuki Yamashita, chief product
[00:08:48] officer at Figma, also a former head of design at Uber.
[00:08:53] Yuki Yamashita, Chief Product Officer at Figma, and described to me
[00:08:54] a time when you’re part of a controversial product assistant, right.
[00:08:58] And, you know, what does it do and all those things.
[00:09:01] And I think it’s, it’s really revealing because, you know, if they can kind of
[00:09:05] like set up this conflict and understand like why this problem is really important
[00:09:09] and represent both sides in a, in such that you can understand why that conflict
[00:09:14] existed in the first place and they can do it in this kind of like even keeled
[00:09:18] way where you realize that they can take on these different perspectives.
[00:09:22] Like you start to learn a lot about that person.
[00:09:24] I think, or sometimes I just ask them for basic things like, okay, talk about
[00:09:28] kind of like a big problem that you worked on and the thought experiment for me is
[00:09:32] always like coming out of that, do I feel compelled to work on that problem?
[00:09:37] Right.
[00:09:37] And no matter how boring it sounds on the surface, like I think a really great
[00:09:41] product manager kind of like cash something is like, well, this is why it’s so existential
[00:09:46] to this and this is why it’s so interesting and like really rallied the troops.
[00:09:49] So that’s kind of one big thing of like storytelling communication, because if they’re
[00:09:54] going to, they like so much of our job, it’s around that.
[00:09:57] Next, you’ll hear from Katie Dill, head of design at Stripe, Kari Saarinen, CEO of Linear
[00:10:03] and Camille Hurst, product leader at Spotify, former product leader at Patreon,
[00:10:08] who all share the same favorite interview question.
[00:10:12] Tell me what work you are most proud of.
[00:10:16] And the reason I ask that is because, well, it helps me understand their taste and their judgment,
[00:10:23] what motivates them.
[00:10:24] What work they view as good and as a good outcome.
[00:10:29] It also helps me understand a little bit about, you know, what they like to do
[00:10:33] and where, you know, their kind of like gravity pulls them.
[00:10:37] I think usually I like to ask, like, what is the candidate most proud of and why
[00:10:41] like on their professional life or otherwise, like what they’re most proud of and why.
[00:10:46] But I think it’s kind of like gives you a little bit indication, like what the person values and
[00:10:50] like how they think about things.
[00:10:52] And I also like, I think it’s always nice.
[00:10:54] Like people can share something like they think they did really well and we can spend time on it
[00:10:59] versus just like asking something like more like negative things.
[00:11:03] I like to ask people to tell me about something they’re really proud of that they accomplished
[00:11:08] and take me through the process and talk to me about why they’re proud of it.
[00:11:14] And I find you can learn so much about a person’s motivations, about their work ethic,
[00:11:19] about what they care about, like what good looks like to them.
[00:11:24] And I think that’s really important.
[00:11:24] And I think those are all really important things to understand about a person if you’re
[00:11:27] going to work closely with them.
[00:11:29] Next is Jay-Z, head of product at Webflow, former Airbnb colleague,
[00:11:33] sharing her favorite interview question.
[00:11:35] I do like to do behavioral questions.
[00:11:37] It’s really understanding like when they’ve been in challenging situations,
[00:11:40] when they’ve been in ambiguous situations, like how do they navigate ambiguity is a big one for me.
[00:11:46] Because at the end of the day, like the PM job is really ambiguous.
[00:11:49] Like it’s really hard to describe on a piece of paper all the things that you’re going to encounter.
[00:11:52] Good answers are.
[00:11:54] People who put structure and a way forward through the ambiguity, like that’s what you look for.
[00:12:00] Like you want your PM to not just be like, oh, no, we’re swimming in ambiguity,
[00:12:03] but like actually put a path forward.
[00:12:05] I think also looking for people who are like seeking help, seeking those inputs,
[00:12:11] as opposed to being like, this is the way this is very clear.
[00:12:13] Because again, the chances of whatever path you chart out for any product,
[00:12:17] for anything that you’re doing is like the right path from the first time that you do it.
[00:12:21] So rare.
[00:12:22] And so I want to see someone be able to like get those.
[00:12:24] Yeah.
[00:12:24] Yeah.
[00:12:24] Be able to like say like, this is the path.
[00:12:26] This is how I like learn why, you know, I put this path together.
[00:12:29] And then going back to a lot of the stuff I think we touched upon in this podcast is like,
[00:12:33] what are the little milestones that make you say, hey, is this working?
[00:12:37] Is this not working?
[00:12:38] And then make you either make a different decision.
[00:12:40] Seeing people do that really well is a big thing I look for.
[00:12:44] Next up is Noah Weiss, chief product officer at Slack.
[00:12:48] What unfair secrets have you learned to improve the velocity and energy level
[00:12:54] of a product to you?
[00:12:56] Am I saying unfair or secret?
[00:12:58] I usually mean like not something that you probably read on like a medium.
[00:13:02] What did you learn?
[00:13:03] How did you learn it?
[00:13:04] And how does it work?
[00:13:05] And how do you apply it?
[00:13:07] You also just get amazing, interesting, like bits of inspiration from asking that.
[00:13:11] This next question comes from the very sultry voice of Ben Williams,
[00:13:15] former VP of product at Snyk and now an advisor to product-led growth startups.
[00:13:22] Fast forward three years.
[00:13:23] What’s different about you then a lot of people will default to telling you where
[00:13:28] they aspire to be in terms of role or title, but what I’m really looking for is
[00:13:32] signals of humility of self-awareness around areas of personal and professional
[00:13:38] growth.
[00:13:38] So no people who can be open about where they think they need to work on to, to
[00:13:46] grow themselves as people.
[00:13:48] I love that.
[00:13:49] Also, just generally throughout interviews.
[00:13:52] I’m looking for.
[00:13:53] I’m looking for curiosity.
[00:13:54] So day to day, good PMs will be asking why as much as my six-year-old son does, which is a lot.
[00:14:02] So I’ll try and discern that through the course of the conversation.
[00:14:05] It’s not really a question, but something I’m looking for.
[00:14:08] And then maybe I want to flip it because building on something that Adam Fishman was saying, his
[00:14:15] theme of evaluating the people dimension of folks, you’re potentially going to work with when you’re
[00:14:19] interviewing with a company.
[00:14:21] And this was a question I got asked myself.
[00:14:23] Recently by a candidate, which I just thought was brilliant.
[00:14:25] And that was, tell me about the diversity, equity, inclusion, and belonging initiatives that you’ve recently
[00:14:31] personally been involved with.
[00:14:32] And that, it just felt like a really great way for them to be able to test alignment of their personal values with
[00:14:38] those of someone they’d be working with really closely.
[00:14:40] So I love that.
[00:14:42] Next up is Meltem Koran Berkowitz, head of growth and a very early employee at deal.
[00:14:48] What would your siblings say about you?
[00:14:51] It’s very telling.
[00:14:52] If they have siblings, if they don’t, I will say, what will your parents say about you?
[00:14:56] But it’s very telling what you think other people think of you.
[00:15:00] What do you look for in their answer that gives you a sign that they’re a good candidate or not?
[00:15:05] I look for sincerity and self-awareness.
[00:15:07] Like your siblings are never, I mean, I love my sister, but she’ll probably should talk to me a lot.
[00:15:12] And being aware of that is very important.
[00:15:14] Like if someone’s like my siblings will say I’m very organized and that I’m the one that brings our family together.
[00:15:19] Like that’s probably a bullshit answer.
[00:15:21] But if they’re like.
[00:15:22] Like, oh yeah, like they’ll say these weird things about me that shows a little bit of like self-awareness and humbleness that I want to see in a person.
[00:15:30] Next is Paige Costello, co-head of product management and also head of AI at Asana.
[00:15:36] I like to ask, tell me about a time something went wrong.
[00:15:41] What was it?
[00:15:42] What did you do about it?
[00:15:43] And effectively the question gets that when, when the product failed, when something about the team didn’t work, just.
[00:15:52] Things that go wrong because that’s what happens when you’re doing this work and evaluating people’s mindset and the way they talk about it and the way they relate to evaluating the situation.
[00:16:05] And I think it’s a great question.
[00:16:07] Really tells you a lot about how people think and how they perceive themselves when things are not working well.
[00:16:14] We are in the final stretch now.
[00:16:16] There’s only five more interview questions to go.
[00:16:18] Next up is Nikhil Singhal, VP of product at Facebook.
[00:16:22] Also one of the most popular episodes of the podcast.
[00:16:25] What’s something that everyone takes for granted that you think is essentially hogwash or inaccurate?
[00:16:33] You know, sometimes I’ll ask a manager, look, you’ve managed, you know, hundreds of people in your career.
[00:16:38] What’s conventional wisdom that you bet against that you have found exactly actually inaccurate.
[00:16:45] And you can do that for what do people think about AI?
[00:16:48] That’s inaccurate that everyone believes you could do that for, you know, domain.
[00:16:52] And you can do all kinds of things.
[00:16:53] I’m always looking for people to break this sort of interview mindset.
[00:17:01] So everyone always prepares for interviews and then their entire conversation is predicting what you think you want me to say.
[00:17:12] And as a result, you can have high quality people that you dismiss because they weren’t genuine.
[00:17:19] There’s no way to answer that question.
[00:17:22] Without being genuinely opinionated.
[00:17:25] Because it starts with what is the thing that you think I want to say here and then tell me why it’s inaccurate.
[00:17:35] So when I break that wall, I’m testing is this person authentic?
[00:17:41] Because sometimes I’m dismissing them because they gave me, they told me nothing new.
[00:17:45] But I don’t want the interview process to penalize them.
[00:17:49] And this was my save question.
[00:17:52] This next question comes from Ayo Omojalo, chief product officer at Carbon Health, former product lead at Square, and also a former founder.
[00:18:01] Tell me something you did that worked out, but not for the reason that you thought it would work.
[00:18:06] Or tell me something you did that was a good decision that didn’t work.
[00:18:09] A lot of like my process is just teasing out introspection.
[00:18:12] It’s just like, are you a person who is reflective about like 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.
[00:18:21] Next up.
[00:18:22] Is Scott Belsky, chief strategy officer at Adobe, former chief product officer of Adobe, also former founder of Behance.
[00:18:30] I like asking about something people have learned about themselves that reveal the limitation in how they work.
[00:18:38] You know, it’s a way to test like introspection.
[00:18:41] And when this person hits their limits or struggles, can they be open and introspective?
[00:18:45] Are they going to blame and point fingers?
[00:18:48] So I do ask that.
[00:18:49] I also like the question that do you consider yourself lucky?
[00:18:52] I think it’s a fascinating question because it also, you know, some people who are super insecure about, you know, where where they are and how they got there might decline admitting luck.
[00:19:05] You know, those who are comfortable should admit that they were lucky.
[00:19:08] I mean, I think the truth is we’re all very lucky and and certainly privileged.
[00:19:14] And, you know, I just think that that’s always an interesting conversation.
[00:19:18] Our penultimate interview question comes from Lauren Isford, head of growth at Notion.
[00:19:22] Former head of growth at Airtable.
[00:19:25] Tell me about a time that you delivered something that was impactful.
[00:19:31] I’m looking for someone to help me understand how they define impact and what it means to them.
[00:19:39] I think a good answer for growth practitioner is intrinsic motivation about having an impact on the business.
[00:19:46] Our final interview question is actually advice for doing reference calls, which comes after.
[00:19:52] And this comes from Paul Adams, chief product officer at Intercom with his killer Irish accent.
[00:20:00] I had to do referral calls.
[00:20:02] So like you’re interviewing someone, you want to give them the job and they’ve got referees.
[00:20:05] And of course, the referees they have are like the best people that they ever worked with and their favorite managers.
[00:20:09] So this question is, what feedback will I be giving this person in their first performance review?
[00:20:15] That’s an amazing question because the person can’t dodge it.
[00:20:18] You know, there’s an answer.
[00:20:20] And it’s incredibly enlightening.
[00:20:22] And it’s a wrap.
[00:20:25] Thank you so much for listening.
[00:20:26] I hope you found this valuable.
[00:20:27] Leave a comment either on the newsletter post or in the YouTube comments or even on Twitter.
[00:20:32] Let me know what you think.
[00:20:33] If there’s a great response, we’ll continue to do this.
[00:20:35] If not, we’ll never do this again.
[00:20:37] All right. Thank you.
[00:20:38] Enjoy.