Lenny's PodcastMy favorite interview questions from 100+ guests
At a glance
WHAT IT’S REALLY ABOUT
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.
IDEAS WORTH REMEMBERING
5 ideasUse 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)?” or “Fast-forward three years, what’s different about you?” push candidates to reflect honestly on their strengths, limitations, and growth areas rather than hiding behind generic humility.
Test how candidates handle difficulty, ambiguity, and failure, not just success.
Prompts such as “What’s the hardest thing you’ve ever done?”, “Tell me about a time something went wrong,” or “Describe a controversial product decision you were part of” reveal resilience, ownership, learning mindset, and collaborative problem-solving under real pressure.
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.
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.
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?” or “Tell me something that worked but not for the reason you expected” force candidates out of scripted answers and into authentic, nuanced thinking.
WORDS WORTH SAVING
5 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
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