Nov 29, 2023 · 20m · lennys-podcast
My favorite interview questions from 100+ guests
Lenny Rachitsky · 5m spoken Shishir Mehrotra · 3m spoken Nikhyl Singhal · 1m spoken Ben Williams · 1m spoken Jiaona Zhang · 1m spoken Yuhki Yamashita · 59s spoken Scott Belsky · 42s spoken Meltem Kuran Berkowitz · 33s spoken Paige Costello · 32s spoken Karri Saarinen · 25s spoken Geoff Charles · 24s spoken Camille Hearst · 24s spoken Katie Dill · 23s spoken Paul Adams · 20s spoken Noah Weiss · 19s spoken Aika Demigliano · 19s spoken Ayo Omojola · 18s spoken Lauryn Isford · 18s spoken
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Host Lenny Rachitsky compiles seventeen standout interview questions from top product leaders and tech executives, providing a practical framework for evaluating candidates' self-awareness, problem-solving abilities, and operational leadership.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Lenny holds 30% of the talking time here. How this is scored →
Lenny as informed peer 0.6 Guest teaching 4.0 Guest disagreement 0.6 Lenny pushing back 0.2
speaking balance: gold is Lenny, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 16:25 Nikhil Singhal calling out interview hogwash
Nikhil takes an assertive stance against scripted interview performance, seeking candidates who will directly challenge conventional wisdom and call out falsehoods.
Hardest push from Lenny ▶ 15:01 Lenny pressing Meltem for evaluation criteriaLenny interjects to demand specific criteria for distinguishing good answers from bad answers regarding sibling perception.
Biggest teaching moment ▶ 5:30 Shishir Mehrotra explaining eigenquestion quadrantsShishir breaks down how two simple questions about safety and CapEx/OpEx map directly to strategic business models.
Lenny holds their own ▶ 4:31 Lenny contextualizing viral audience reachLenny demonstrates his platform's reach and curation expertise by contextualizing the viral impact of Shishir's framework across short-form media.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Lenny as informed peer | Guest teaching | Guest disagreement | Lenny pushing back | Why |
|---|---|---|---|---|---|---|
| Aika Demigliano: Attributing Success Without Saying Luck | 1 | 5 | 1 | 0 | Lenny curates clip submissions from product leaders. Shishir Mehrotra provides an extensive masterclass on breaking down complex problems using the teleportation eigenquestion framework. | |
| Yuki Yamashita: Navigating Controversy and Compelling Storytelling | 0 | 3 | 0 | 0 | Lenny acts purely as an introductory narrator while Yuki Yamashita, Katie Dill, Karri Saarinen, and Camille Hearst share their favorite interview questions around conflict and pride. | |
| Jiaona Zhang: Navigating Ambiguity in Product Management | 0 | 4 | 0 | 0 | Jiaona Zhang, Noah Weiss, and Ben Williams describe assessing ambiguity navigation, unfair advantages, and personal humility without any host pushback. | |
| Meltem Kuran Berkowitz: What Siblings Would Say | 2 | 4 | 2 | 1 | Lenny briefly interacts to prompt Meltem on what she looks for in sibling answers. Nikhil Singhal passionately explains his strategy for puncturing rehearsed interview BS. | |
| Ayo Omojola: Decision-Making Introspection and Outcomes | 0 | 4 | 0 | 0 | Ayo Omojola, Scott Belsky, Lauren Isford, and Paul Adams provide rapid-fire clips on introspection, impact, and reference-checking tactics in a curated montage format. |
Statements from this episode (12)
Demigliano: Banning 'luck' as an answer reveals a candidate's self-awareness.
“To what do you attribute your success and you can't say luck? Cause you know, I think humble people will always say luck in some way. And you know, I always kind of wanted to like, did you like, how self-aware are you basically? And I think, and how curious ar…”
Charles: Asking about a candidate's hardest challenge reveals agency and grit.
“I asked, what's the hardest thing you've ever done? And I asked that because working at ramp is hard. I want to understand like what hard means for them. I want to understand why it was hard. I want to understand how they overcame that difficulty, how they wor…”
Mehrotra: Kids naturally simplify strategic problems much better than adult candidates.
“Kids are incredibly good at simplifying these things down. It's actually a skill we like remove from ourselves.”
Yamashita: Great PMs make seemingly boring problems feel existential and compelling.
“No matter how boring it sounds on the surface, like, I think a really great product manager kind of, like, cast something as like, well, this is why it's so existential to us, and this is why it's so interesting, and like, really rallying the truth.”
Dill: Asking candidates what they are proudest of reveals their taste.
“And the reason I ask that is because, well, it helps me understand their taste and their judgment, what motivates them, what work they view as good and as a good outcome. It also helps me understand a little bit about, you know, what they like to do and where,…”
Zhang: Strong PM candidates create structure and define paths through ambiguity.
“Good answers are people who put structure and a way forward through the ambiguity. Like that's what you look for. Like you want your PM to not just be like, oh no, we're swimming in ambiguity, but like actually put A path forward.”
Weiss: Asking candidates for their 'unfair secrets' yields practical operational insights.
“If I say unfair or secret, I usually mean, like, not something that you probably read on, like, a medium, but like, what did you learn? How did you learn it? And how does it work? And how do you apply it? You also just get amazing, interesting, like, bits of i…”
Berkowitz: Asking what siblings think reveals insincerity if answers are polished.
“Like if someone was like, my siblings will say I'm very organized and that I'm the one that brings our family together. Like that's probably a bullshit answer. But if they're like, oh yeah, like they'll say these weird things about me that shows a little bit o…”
Singhal: Candidates often fail by trying to predict what interviewers want.
“Everyone always prepares for interviews and then their entire conversation is predicting what you think you want me to say. And as a result, you can have high quality people that you dismiss because they weren't genuine.”
Singhal: Asking candidates to challenge conventional wisdom forces genuine opinions.
“There's no way to answer that question without being genuinely opinionated.”
Belsky: Asking candidates about their personal limitations tests for blame deflection.
“I like asking about something people have learned about themselves that reveal the limitation in how they work. You know, it's a way to test like introspection and when this person hits their limits or struggles, can they be open and introspective or are they …”
Adams: Asking references to predict the first review prevents dodging constructive feedback.
“So this question is what feedback will I be giving this person in their first performance review? And it's an amazing question because the person can't dodge it. You know, there's an answer and it's incredibly enlightening.”