Lenny's PodcastMy favorite interview questions from 100+ guests
CHAPTERS
- 0:00 – 0:30
Why this episode exists: 17 standout interview questions from 100+ guests
Lenny explains that one of the most-loved podcast segments is the lightning round—especially guests’ favorite interview questions and what good answers reveal. This episode curates 17 of the best questions into a single, reusable resource for interviewers and candidates alike.
- •Lightning round interview questions are a listener favorite
- •Compilation of 17 best questions from 100+ podcast guests
- •Useful for building interview loops, improving existing questions, or prepping as a candidate
- 0:30 – 3:01
Sponsor break: Sendbird (in-app communication APIs) + Eppo (experimentation platform)
Lenny shares two sponsor messages. The first highlights Sendbird’s in-app communication suite; the second highlights Eppo’s A/B testing and feature management platform aimed at increasing experimentation velocity and rigor.
- •Sendbird: chat, bots, messages, video, live stream; emphasis on in-app conversion/engagement
- •Listener offer for Sendbird plan and premium access
- •Eppo: experimentation + deep analysis, faster cycles, accessible UI and reporting
- •Use cases across product, growth, ML, monetization, marketing
- 3:01 – 3:58
Self-awareness without the easy out: “To what do you attribute your success (and you can’t say luck)?”
The first featured question probes how candidates explain their success when “luck” is removed as a default answer. The goal is to surface self-awareness and curiosity via thoughtful reflection on what truly drove outcomes.
- •Forces reflection beyond a humble “it was luck” response
- •Reveals self-awareness about strengths, choices, and habits
- •Signals curiosity about cause-and-effect in one’s own career
- 3:58 – 4:31
Calibrating what “hard” means: “What’s the hardest thing you’ve ever done?”
Jeff Charles uses this to understand a candidate’s relationship with difficulty—what they consider hard, why it was hard, and what they did about it. It also teases out agency and how they collaborate to overcome obstacles.
- •Defines the candidate’s threshold and understanding of difficulty
- •Explores problem-solving process and perseverance
- •Looks for agency vs. passivity in tough situations
- •Assesses collaboration in overcoming challenges
- 4:31 – 8:45
The teleportation “eigenquestion” test: asking the right two questions, then making a plan
Shishir Mehrotra’s thought experiment tests whether candidates can find the few highest-leverage questions that unlock a plan. After letting candidates ask freely, he constrains them to only two questions—revealing prioritization, decision-driven thinking, and simplification skills.
- •Fictional scenario lowers stakes and reveals real thinking patterns
- •Constraint (only 2 questions) forces prioritization and clarity
- •Strong answers tie questions directly to decisions and strategy
- •Evaluates ability to simplify and structure ambiguous problems
- 8:45 – 9:57
Handling conflict and selling the problem: controversial decisions + compelling storytelling
Yuhki Yamashita asks candidates to describe a controversial product decision to see if they can represent both sides fairly and explain the underlying conflict. He also gauges whether candidates can make any “big problem” feel motivating and existential through strong narrative.
- •Assesses ability to set up conflict and explain stakes
- •Looks for even-keeled perspective-taking and empathy
- •Measures communication and storytelling—a core PM skill
- •Tests whether a candidate can inspire others to care about a problem
- 9:57 – 11:29
What you’re proud of (and why): taste, values, motivation, and what “good” looks like
Katy Dill, Karri Saarinen, and Camille Hearst all favor a pride-based question to learn what candidates value and how they judge quality. The focus is on choices, process, and the candidate’s definition of excellence—not just the outcome.
- •Reveals taste, judgment, and standards for quality
- •Surfaces intrinsic motivation and personal values
- •Highlights what kind of work energizes the candidate
- •Lets interviewers dig into process, not just results
- 11:29 – 12:44
Navigating ambiguity with structure: how candidates create a path forward
Jiaona Zhang emphasizes behavioral questions about challenging and ambiguous situations. Great answers show structured thinking, milestone-setting, learning loops, and the willingness to seek input rather than over-commit to a single “clear” path.
- •PM work is inherently ambiguous; candidates must show comfort with it
- •Strong candidates create structure and forward motion
- •Looks for input-seeking and iterative course correction
- •Milestones and check-ins reveal a learning-oriented approach
- 12:44 – 13:11
“Unfair secrets” for team velocity: practical, non-obvious operating insights
Noah Weiss asks for “unfair secrets” that increase a product team’s energy and velocity—ideas learned through experience rather than generic advice. The framing draws out concrete practices and the candidate’s ability to translate lessons into repeatable methods.
- •Seeks non-generic, experience-earned insights
- •Tests how candidates learn and apply operating tactics
- •Encourages specificity: what it is, how it was learned, how it works
- •Produces useful inspiration for interviewers as well
- 13:11 – 14:42
Three-year personal growth + value alignment: humility, curiosity, and DEIB leadership signals
Ben Williams’ question focuses on who the candidate becomes in three years—pushing past title talk toward humility and self-awareness about growth areas. He also highlights curiosity as a consistent signal and shares a candidate-led question that probes DEIB actions for values alignment.
- •“What’s different about you in three years?” surfaces growth mindset vs. title-chasing
- •Looks for humility and self-awareness about development needs
- •Curiosity is treated as an always-on evaluation criterion
- •Candidate question on DEIB initiatives tests real value alignment and leadership involvement
- 14:42 – 15:30
Third-person honesty check: “What would your siblings (or parents) say about you?”
Meltem Kuran Berkowicz uses a family-perspective question to reveal sincerity and self-awareness. Overly polished answers can be a red flag, while nuanced, imperfect observations suggest authenticity and humility.
- •Tests self-awareness through perceived external feedback
- •Sincerity matters more than flattering traits
- •Overly idealized descriptions can signal inauthenticity
- •Humility and realism are positive indicators
- 15:30 – 16:15
Learning from failure: “Tell me about a time something went wrong—what did you do?”
Paige Costello asks candidates to walk through a failure or breakdown to understand mindset and self-perception when things aren’t working. The value is in how they diagnose, respond, and learn—not in presenting a spotless track record.
- •Surfaces accountability and response under pressure
- •Reveals how candidates diagnose messy situations
- •Evaluates learning orientation vs. defensiveness
- •Shows how they collaborate and adapt when plans fail
- 16:15 – 17:52
Authentic contrarian thinking: challenging conventional wisdom without “interview mode”
Nikhyl Singhal asks what widely accepted belief the candidate thinks is inaccurate, forcing a genuinely opinionated response. It’s designed to break rehearsed interview scripts and surface authenticity, independent thinking, and clarity of reasoning.
- •Forces candidates to share a real point of view
- •Breaks the pattern of telling interviewers what they want to hear
- •Tests critical thinking and willingness to challenge assumptions
- •Useful across domains (management, AI, product, etc.)
- 17:52 – 18:21
Outcome vs. reasoning: good decisions that fail and lucky wins you misunderstood
Ayo Omojola’s question separates decision quality from outcomes by probing cases where things worked for unexpected reasons—or didn’t work despite being a good call. It targets introspection and whether candidates update their mental models based on what happened.
- •Distinguishes decision-making quality from results
- •Tests introspection about causality and assumptions
- •Looks for model-updating: what they’d do differently next time
- •Encourages nuanced thinking about uncertainty
- 18:21 – 20:45
Limits, luck, impact—and a killer reference-check question
Scott Belsky explores self-knowledge about personal limitations and asks whether candidates consider themselves lucky, both of which reveal introspection and comfort with privilege and uncertainty. Lauryn Isford focuses on how candidates define “impact,” and Paul Adams’ reference-call question uncovers likely performance feedback early.
- •Self-limitations question tests introspection vs. blame
- •“Do you consider yourself lucky?” reveals comfort, humility, and perspective
- •“Delivered something impactful” clarifies how candidates define and pursue impact
- •Reference check: “What feedback will I give in their first performance review?” is hard to dodge and highly revealing
