My favorite interview questions from 100+ guests

My favorite interview questions from 100+ guests

Lenny's PodcastNov 29, 202320m

Lenny Rachitsky (host), Rahul Vohra (guest), Jeff Charles (guest), Shishir Mehrotra (guest), Yuhki Yamashita (guest), Katy Gill (guest), Karri Saarinen (guest), Camille Hearst (guest), JZ (Jiaona Zhang) (guest), Noah Weiss (guest), Narrator, Ben Williams (guest), Meltem Kuran Berkowicz (guest), Paige Costello (guest), Nikhyl Singhal (guest), Ayo Omojola (guest), Scott Belsky (guest), Lauren Isford (guest), Shane Parrish (guest)

High-signal interview questions used by top product and growth leadersAssessing self-awareness, humility, and introspection in candidatesEvaluating problem-solving, ambiguity navigation, and eigenquestion thinkingIdentifying motivations, values, and definitions of impact and successBehavioral questions around failures, controversy, and hard challengesSignals of communication, storytelling ability, and stakeholder alignmentReference-checking techniques that surface realistic developmental feedback

In this episode of Lenny's Podcast, featuring Lenny Rachitsky and Rahul Vohra, My favorite interview questions from 100+ guests explores seventeen Proven Interview Questions Top Product Leaders Reliably Swear By This episode compiles 17 favorite interview (and reference) questions from over 100 guests on Lenny’s Podcast, most of them senior product and growth leaders. Each guest explains the intent behind their question and what a strong answer reveals about a candidate. Themes include self‑awareness, judgment, storytelling, handling ambiguity, introspection, and authentic opinions. The episode doubles as a toolkit for both interviewers designing better processes and candidates preparing for high‑caliber product interviews.

Seventeen Proven Interview Questions Top Product Leaders Reliably Swear By

This episode compiles 17 favorite interview (and reference) questions from over 100 guests on Lenny’s Podcast, most of them senior product and growth leaders. Each guest explains the intent behind their question and what a strong answer reveals about a candidate. Themes include self‑awareness, judgment, storytelling, handling ambiguity, introspection, and authentic opinions. The episode doubles as a toolkit for both interviewers designing better processes and candidates preparing for high‑caliber product interviews.

Key Takeaways

Use questions that force self-awareness instead of safe, rehearsed answers.

Questions like “To what do you attribute your success (and you can’t say luck)? ...

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Test how candidates handle difficulty, ambiguity, and failure, not just success.

Prompts such as “What’s the hardest thing you’ve ever done? ...

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Probe for clear thinking through constrained problem-framing and eigenquestions.

Shishir Mehrotra’s teleportation device exercise—limiting candidates to two questions—shows who can identify the few ‘eigenquestions’ that truly drive a decision, a powerful signal of strategic, structured thinking for any product role.

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Ask about work people are proud of to uncover taste, motivation, and standards.

Variations of “Tell me about work you’re most proud of and why” consistently surface what candidates value, what ‘good’ looks like to them, and whether their intrinsic motivations and quality bar align with your team’s culture and expectations.

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Look for genuine, non-obvious opinions to break through interview performance mode.

Questions like “What’s something everyone takes for granted that you think is wrong? ...

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Explicitly evaluate curiosity, learning loops, and introspection as core PM skills.

Many leaders scan for candidates who routinely ask ‘why,’ seek input, adapt based on milestones, and can articulate what they’ve learned about themselves and their decision-making over time—key traits for navigating inherently ambiguous product work.

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Use sharper reference questions to access honest developmental feedback.

Paul Adams’s reference question—“What feedback will I be giving this person in their first performance review? ...

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Notable Quotes

“To what do you attribute your success? And you can't say luck.”

Eka Damiliano

“I ask, ‘What’s the hardest thing you’ve ever done?’… I want to understand what hard means for them.”

Jeff Charles

“A group of scientists have invented a teleportation device… they will answer only two of your questions. What two questions do you ask?”

Shishir Mehrotra

“Tell me what work you are most proud of.”

Katy Gill / Karri Saaranen / Camille Hearst

“What feedback will I be giving this person in their first performance review?”

Paul Adams

Questions Answered in This Episode

How could these interview questions be adapted for non-product roles while preserving their diagnostic power?

This episode compiles 17 favorite interview (and reference) questions from over 100 guests on Lenny’s Podcast, most of them senior product and growth leaders. ...

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Which of these questions best differentiates high-potential junior candidates from more experienced but average performers?

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How can teams calibrate on what ‘good’ looks like in answers to subjective, introspection-heavy questions?

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What are potential drawbacks or biases introduced by relying heavily on unconventional or opinion-based questions?

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How might a candidate preparing for interviews systematically practice responding to these specific prompts without sounding overly rehearsed?

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Transcript Preview

Lenny Rachitsky

(instrumental music) . Welcome to a very special episode of the podcast. Ever since I started this podcast, one of people's favorite segments continues to be the lightning round. And in particular, a question I ask guests around their favorite interview question that they like to ask candidates and what they look for in a good answer. What we've done is we've picked my favorite interview questions that guests have shared. Out of over a hundred guests on the podcast, we've got 17 of my favorite interview questions all combined in this one episode. You can use this episode anytime you are preparing to interview candidates, if you want to improve your existing interview questions, or if you're about to get interviewed and you want to prepare for the kinds of questions that you might get in the interview process. Before we dive in, let me tell you about our product called Sendbird, the all-in-one communications API platform designed for both web and mobile apps. In a world saturated with multi-channel communication, product teams are discovering the effectiveness of in-app communication. With Sendbird, businesses can elevate their in-app experience with decluttered and branded communication featuring AI-powered chatbots, one-way messages, chat, video calls, and live stream capabilities, all tailored for commerce, marketing, and top-tier support. Forward-thinking companies such as Hinge, Patreon, Yahoo, Accolade, and more use Sendbird to build in-app communication experiences that drive engagement, conversion, and retention. In-app communication has the highest conversion, highest engagement, and highest satisfaction of any communication channel. And when it comes to investing in this channel, trust Sendbird to take your in-app communication experience to the next level. Start today with Sendbird's free plan and as a listener of Lenny's Podcast, you'll get an additional two months of unlimited usage and access to all premium features, including creating your very own generative AI chatbot. Visit sendbird.com/lenny to begin your free journey. That's sendbird.com/lenny. This episode is brought to you by Eppo. Eppo is a next generation A/B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and DraftKings rely on Eppo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features. And Eppo helps you increase experimentation velocity while unlocking rigorous deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own. Eppo does all that and more with advanced statistical methods that can help you shave weeks off experiment time, an accessible UI for diving deeper into performance, and out-of-the-box reporting that helps you avoid annoying prolonged analytic cycles. Eppo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A/B testing flywheel. Eppo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Eppo at geteppo.com/lenny and 10X your experiment velocity. That's geteppo.com/lenny. First up, we've got Eka Damiliano. Eka was head of product at Retool. She was also a PM at Stripe. Currently, she's actually starting her own company. And so here's Eka sharing her favorite interview question.

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