29 November 2023

My favorite interview questions from 100+ guests

9Frameworks

15Insights

Episode overview

Lenny Rachitsky compiles 17 favorite interview questions shared by more than 100 past podcast guests. Product, design, growth, and company leaders explain how their questions reveal candidates' self-awareness, judgment, resilience, curiosity, authenticity, and ability to navigate ambiguity. The episode closes with Paul Adams's reference-call question about the feedback a new hire will receive in their first performance review.

Key ideas

Ask candidates to explain their success without defaulting to luck.
Probe difficult or failed work to understand agency, reflection, and resilience.
Constrain hypothetical cases to expose which questions actually drive decisions.
Proud-work questions reveal taste, values, motivation, and definitions of quality.
Strong product candidates create structure, seek input, and set milestones amid ambiguity.
Contrarian questions can break rehearsed interview behavior and surface authentic opinions.
Reference checks become more revealing when framed around a future first performance review.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Leadership5 steps

The Ambiguity Navigation Rubric

Score behavioural answers on three axes: did they impose structure, seek inputs, and define milestones?

Read →

Communication5 steps

The Compelled Test (Storytelling as Product Signal)

After they describe a big problem, measure your own reaction — do you feel compelled to go work on it?

Read →

Self-Mastery6 steps

The Constrained Self-Awareness Probe

Remove the humble answer, borrow someone else's eyes, or jump three years forward — self-awareness can't hide.

Read →

Leadership4 steps

The First Performance Review Reference Call

Ask a cherry-picked referee what feedback you'll give the candidate at their first review — they can't dodge it.

Read →

Leadership6 steps

The Hardest Thing Test (Calibrating Difficulty and Agency)

Ask what's the hardest thing they've ever done, then extract their difficulty bar and how much agency they had.

Read →

Leadership4 steps

The Hogwash Question (Breaking the Interview Mindset)

Ask what conventional wisdom is inaccurate — it's unanswerable without genuine opinion, so it exposes authenticity.

Read →

Mindset4 steps

The Introspection Probe (Decoupling Decisions from Outcomes)

Ask for a win that worked for the wrong reason, or a good call that failed — outcome-blind introspection tests.

Read →

Leadership5 steps

The Proudest Work Question (Taste Triangulation)

Ask what work they're proudest of and why — it exposes taste, standards, motivation, and where their gravity pulls.

Read →

Leadership6 steps

The Teleportation Device Test (Finding the Important Question)

Cap a candidate to two questions on a fictional problem to reveal whether they can find the decision-driving question.

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 18

Lenny RachitskyCoinedtoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter
“ever since I started this podcast one of people's favorite segments continues to be the lighting round”
▶ Watch at ~0:00approx.
Jeff CharlesMentionsI recently did a newsletter post on how Ram builts product with their VPR product Jeff Charles
“next up we've got Jeff Charles head of product at ramp”
▶ Watch at ~3:30approx.
Shishir MehrotraMentionsshashir marocha is the co-founder and ceo of koda before starting koda shashir led the youtube product engineering and design teams
“next up we've got shashir marra CEO and co-founder of Kota”
▶ Watch at ~4:30approx.
Yuki YamashitaMentionsChief product officer at Figma and former head of design at Uber.
“this next interview question comes from Yuki Yamashita Chief product officer at figma also a former head of design at Uber”
▶ Watch at ~8:30approx.
Camille HearstMentionsCamille is head of fan monetization at Spotify. Before that, she was head of product for creators at Patreon.
“Camille Hurst product leader at Spotify former product leader at patreon”
▶ Watch at ~9:30approx.
Katie DillMentionsKatie is head of design at stripe where she over product design brand and marketing creative web presence user research content strategy and design Ops
“next you'll hear from Katie Dill head of design at stripe”
▶ Watch at ~9:30approx.
Karri SaarinenMentionsKi was the founding designer coinbase principal designer at Airbnb co-founder of two previous startups and most recently is the co-founder and CEO of linear
“Ki sarin CEO of linear”
▶ Watch at ~9:30approx.
Jiaona ZhangMentionsJay-Z is senior vice president of product at webflow she's also a lecturer at Stanford teaching a course on product management
“next is Jay-Z head of product at webflow former Airbnb colleague sharing her favorite interview question”
▶ Watch at ~11:00approx.
Noah WeissMentionsNoah is Chief product officer at slack where he spent the last seven years
“next up is Noah Weiss Chief product officer at slack”
▶ Watch at ~12:30approx.
Ben WilliamsMentionsBen Williams who's a previous guest on this podcast who suggested you join this podcast and who connected us
“Ben Williams former VP product at sneak and now an adviser to product Le growth startups”
▶ Watch at ~13:00approx.
Adam FishmanMentionsI've been a chief product officer and VP of growth and product at a bunch of different companies imperfect Foods patreon Lyft
“building on something um that Adam Fishman was saying his theme of evaluating the people dimension”
▶ Watch at ~14:00approx.
Meltem Kuran BerkowitzMentionsHead of growth and an early employee at Deel.
“next up is melum Quan burwitz head of growth and a very early employee at deal”
▶ Watch at ~14:30approx.
Paige CostelloMentionsPaige is a product lead at Asana overseeing teams responsible for the core product experience of Asana
“next is Paige Castello co-head of product management and also head of AI at assana”
▶ Watch at ~15:00approx.
Nikhyl SinghalMentionsnickel has worked on and led large teams on four different influential consumer products including Facebook Credit Karma Google Hangouts and Google photos
“next up is Nel singal PP of product at Facebook”
▶ Watch at ~16:00approx.
Iyo OmojolaMentionsChief product officer at Carbon Health, former product lead at Square, and former founder.
“this next question comes from IO omalo Chief product officer at Carbon Health former product lead at square and also a former founder”
▶ Watch at ~17:30approx.
Scott BelskyMentionsHe's a former founder starting a company called Behance that he sold to Adobe where he worked up the ranks to chief product officer
“next up is Scott bsky Chief strategy officer at Adobe former Chief product officer of adobe Al former founder of behance”
▶ Watch at ~18:00approx.
Lauren IsfordMentionswe had a podcast with Lauren Isford from formerly Airtable now Notion
“our penultimate interview question comes from Lauren isord head of growth at notion former head of growth at air table”
▶ Watch at ~19:00approx.
Paul AdamsMentionsIntercom's chief product officer and author of a book about AI and customer service.
“this comes from Paul Adams Chief product officer at intercom”
▶ Watch at ~19:30approx.

Resources · 38

Lenny's PodcastCoinedpodcast · Lenny Rachitsky
“ever since I started this podcast one of people's favorite segments continues to be the lighting round”
▶ Watch at ~0:00approx.
AccoladeUsescompany
“companies such as hinge patreon Yahoo Accolade and more use senir”
▶ Watch at ~1:00approx.
HingeUsescompany
“Forward Thinking companies such as hinge patreon Yahoo Accolade and more use senir”
▶ Watch at ~1:00approx.
YahooUsescompany
“companies such as hinge patreon Yahoo Accolade and more use senir”
▶ Watch at ~1:00approx.
PatreonUsescompany
“companies such as hinge patreon Yahoo Accolade and more use senir”
▶ Watch at ~1:00approx.
SendbirdRecommendscompany
“trust sber to take your inep communication experience to the next level start today with sen Bird's free plan”
▶ Watch at ~1:30approx.
AirbnbMentionscompany · Brian Chesky, Joe Gebbia, and Nathan Blecharczyk
“built by alums of Airbnb and snowflake for modern growth teams”
▶ Watch at ~2:00approx.
SnowflakeMentionscompany · Snowflake Inc.
“built by alums of Airbnb and snowflake for modern growth teams”
▶ Watch at ~2:00approx.
TwitchUsescompany
“companies like twitch Muro clickup and DraftKings rely on EPO to power their experiments”
▶ Watch at ~2:00approx.
DraftKingsUsescompany
“companies like twitch Muro clickup and DraftKings rely on EPO to power their experiments”
▶ Watch at ~2:00approx.
ClickUpUsessoftware · ClickUp
“companies like twitch Muro clickup and DraftKings rely on EPO to power their experiments”
▶ Watch at ~2:00approx.
MiroUsessoftware · Miro
“companies like twitch Muro clickup and DraftKings rely on EPO to power their experiments”
▶ Watch at ~2:00approx.
EppoRecommendssoftware · Eppo
“EPO is a Next Generation AB testing and feature management platform”
▶ Watch at ~2:00approx.
StripeMentionscompany · Patrick Collison and John Collison
“she was also a PM at stripe”
▶ Watch at ~3:00approx.
RampMentionscompany · Eric Glyman and Karim Atiyeh
“Jeff Charles head of product at ramp”
▶ Watch at ~3:30approx.
InstagramUsessoftware · Meta
“we posted this exact clip to Tik Tok and Instagram reals”
▶ Watch at ~4:30approx.
TikTokUsessoftware · ByteDance
“we posted this exact clip to Tik Tok and Instagram reals”
▶ Watch at ~4:30approx.
CodaCoinedsoftware · Coda
“shashir marra CEO and co-founder of Kota”
▶ Watch at ~4:30approx.
UberMentionscompany · Uber
“also a former head of design at Uber”
▶ Watch at ~8:30approx.
FigmaMentionssoftware · Figma
“Yuki Yamashita Chief product officer at figma”
▶ Watch at ~8:30approx.
LinearCoinedsoftware · Linear
“Ki sarin CEO of linear”
▶ Watch at ~9:30approx.
SpotifyMentionssoftware · Spotify
“Camille Hurst product leader at Spotify”
▶ Watch at ~9:30approx.
WebflowMentionssoftware · Webflow
“Jay-Z head of product at webflow”
▶ Watch at ~11:00approx.
SlackMentionssoftware · Slack Technologies
“Noah Weiss Chief product officer at slack”
▶ Watch at ~12:30approx.
MediumMentionswebsite · Medium
“not something that you probably read on like a medium po”
▶ Watch at ~12:30approx.
SnykMentionscompany · Guy Podjarny, Danny Grander, and Assaf Hefetz
“Ben Williams former VP product at sneak”
▶ Watch at ~13:00approx.
DeelMentionscompany
“head of growth and a very early employee at deal”
▶ Watch at ~14:30approx.
AsanaMentionssoftware · Asana, Inc.
“Paige Castello co-head of product management and also head of AI at assana”
▶ Watch at ~15:00approx.
FacebookMentionscompany · Meta
“Nel singal PP of product at Facebook”
▶ Watch at ~16:00approx.
Carbon HealthMentionscompany
“IO omalo Chief product officer at Carbon Health”
▶ Watch at ~17:30approx.
SquareMentionscompany · Block, Inc.
“former product lead at square and also a former founder”
▶ Watch at ~17:30approx.
AdobeMentionscompany
“Scott bsky Chief strategy officer at Adobe former Chief product officer of adobe”
▶ Watch at ~18:00approx.
BehanceCoinedwebsite · Scott Belsky and co-founders
“former founder of behance”
▶ Watch at ~18:00approx.
AirtableMentionssoftware · Airtable
“former head of growth at air table”
▶ Watch at ~19:00approx.
NotionMentionssoftware · Notion Labs
“Lauren isord head of growth at notion”
▶ Watch at ~19:00approx.
IntercomMentionscompany · Intercom
“Paul Adams Chief product officer at intercom”
▶ Watch at ~19:30approx.
TwitterUseswebsite · Twitter
“or even on Twitter let me know what you think”
▶ Watch at ~20:00approx.
YouTubeUseswebsite · Google
“leave a comment either on the newsletter post or in the YouTube comments”
▶ Watch at ~20:00approx.

Spot an error or want something removed? Request a correction or removal.

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Story· 1

Story04:30

The teleportation device: which two questions would you ask?

Coda's CEO uses a deliberately made-up scenario — you're the PM bringing a teleportation device to market — and lets candidates ask endless clarifying questions before revealing the twist: the scientists will answer only two. The exercise tests whether someone can rapidly find the one or two questions that actually change the plan, and he notes kids are unusually good at this because they simplify.

Candidates first ask many questions about the device, then are told only two will be answered
Strong PMs quickly isolate the highest-leverage questions (e.g. "is it safe for humans?" and "is it capex or opex expensive?")
Those two answers form quadrants that determine completely different go-to-market strategies
A made-up, low-stakes scenario makes people better at learning the method
Kids simplify to good questions fast — a skill adults train out of themselves

“they've decided that they will answer only two of your questions and after that they expect a plan what two questions do you ask”
05:30

“people's ability to learn the method is significantly higher if it's low stakes”
07:30

#interviewing#product-strategy#first-principles

Q&A· 14

Q&A03:30

"To what do you attribute your success?" — and you can't say luck

A PM leader (former Stripe PM) asks candidates to explain the source of their success, with luck explicitly disallowed as an answer. Because humble people default to crediting luck, forcing a real answer surfaces how self-aware and curious a person is about their own trajectory.

The question bans "luck" as an answer so candidates can't hide behind humility
It tests self-awareness and curiosity
How people reflect on why they are where they are reveals how they think about the world

“to what do you attribute your success and you can't say luck because you know I think humble people will always say luck in some…”
03:30

#interviewing#self-awareness#product-management

Q&A04:00

"What's the hardest thing you've ever done?"

Ramp's head of product asks candidates for the hardest thing they've ever done because the work itself is hard. He's probing what "hard" means to them, why it was hard, how they overcame it, who they worked with, and how much personal agency they had.

The question is asked because the job is genuinely hard
It reveals what difficulty means to the candidate
It surfaces how they overcame difficulty and how much agency they had

“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…”
04:00

#interviewing#resilience#agency

Q&A08:30

"Describe a time you were part of a controversial product decision"

Figma's CPO asks candidates to walk through a controversial product decision and represent both sides of the conflict evenly. Being able to explain why the problem mattered and hold multiple perspectives reveals storytelling ability and whether the interviewer feels compelled to work on the problem too.

Look for candidates who can set up the conflict and represent both sides even-keeled
The thought experiment: does the interviewer come away feeling compelled to work on that problem?
A great PM can make even a boring-sounding problem feel existential and interesting
So much of the PM job is storytelling and communication

“describe to me a time when you're part of a controversial product decision”
08:30

#interviewing#storytelling#product-decisions

Q&A10:00

"Tell me what work you are most proud of"

Three leaders (from Stripe, Linear, and Spotify/Patreon) independently share the same favorite question: what work are you most proud of, and why. It reveals a candidate's taste, judgment, and motivations — what they consider a good outcome — and lets the conversation dwell on something positive rather than probing only failures.

Reveals taste, judgment, and what the candidate views as a good outcome
Shows what a person values and where their gravity pulls them
Asking about pride is a positive frame versus asking about negatives
Walking through the process shows work ethic and what "good" looks like to them

“Tell me what work you are most proud of and the reason I ask that is because well it helps me understand their taste and…”
10:00

“you can learn so much about a person's motivations about their work ethic about what they care about like what good looks like to them”
11:00

#interviewing#taste#motivation

Q&A11:30

How candidates navigate ambiguity

Webflow's head of product uses behavioral questions about challenging, ambiguous situations because the PM job is inherently ambiguous. Good answers show candidates putting structure and a path forward through ambiguity, seeking inputs rather than pretending the path is obvious, and setting milestones to know if it's working.

The PM job is inherently ambiguous and hard to describe on paper
Good answers put structure and a way forward through the ambiguity
Look for people who seek help and inputs instead of declaring the path is clearly right
They should define milestones that signal whether the approach is working

“good answers are people who put structure and and a way forward through the ambiguity like that's what you look for”
11:30

#interviewing#ambiguity#behavioral-questions

Q&A12:30

"What unfair secrets have you learned to improve a team's velocity?"

Slack's CPO asks what unfair secrets a candidate has learned to improve a product team's velocity and energy — deliberately excluding generic advice you'd read in a Medium post. Beyond assessing the candidate, the answers themselves are a source of interesting inspiration.

"Unfair secret" means something not found in a typical Medium post
Asks what they learned, how they learned it, how it works, and how they apply it
The answers double as a source of interesting inspiration for the interviewer

“what unfair Secrets have you learned to improve the velocity and energy level of a product”
12:30

#interviewing#velocity#team-building

Q&A13:00

"Fast forward three years — what's different about you?"

A former Snyk VP of product asks where a candidate will be different in three years, looking past aspirations of role or title for signals of humility and self-awareness about growth areas. He also values a question a candidate once asked him about the interviewer's DEI involvement as a way to test values alignment.

Most people default to naming a future role or title; that's not the goal
He's looking for humility and self-awareness about areas needing growth
He also screens for curiosity throughout the conversation
A candidate asking about the interviewer's own DEI involvement is a smart way to test values alignment

“fast forward three years what's different about you”
13:00

“tell me about the diversity equity inclusion and belonging initiatives that you've recently”
14:00

#interviewing#humility#values-alignment

Q&A14:30

"What would your siblings say about you?"

Deel's head of growth asks what a candidate's siblings (or parents) would say about them. Because siblings are candid, the answer is very telling — she looks for sincerity and self-awareness, including the ability to acknowledge less flattering things others might say.

If they have no siblings, she asks what their parents would say
It's telling what you think other people think of you
She looks for sincerity, self-awareness, and humbleness
Acknowledging the "weird things" others might say signals real self-awareness

“what would your siblings say about you it's very telling if they have siblings if they don't I will say what will your parents say…”
14:30

#interviewing#self-awareness#sincerity

Q&A15:30

"Tell me about a time something went wrong"

Asana's co-head of product management asks candidates about a time something went wrong — a product failure, a team breakdown — because things going wrong is simply part of the work. How they evaluate and talk about the situation reveals their mindset and how they perceive themselves when things aren't working.

Things going wrong is inevitable when doing this work
Evaluates a person's mindset and how they relate to a bad situation
Reveals how people perceive themselves when things are not working well

“tell me about a time something went wrong what was it what did you do about it”
15:30

#interviewing#failure#mindset

Q&A16:00

"What does everyone take for granted that you think is hogwash?"

Facebook's VP of product asks what conventional wisdom a candidate bets against and has found inaccurate. The real purpose is to break the rehearsed interview mindset — there's no way to answer without being genuinely opinionated, which reveals whether the person is authentic rather than just predicting what the interviewer wants to hear.

Can be aimed at any domain — AI, management, whatever conventional wisdom the person holds
People over-prepare and spend interviews predicting what you want to hear
There's no way to answer without being genuinely opinionated
Breaking that wall prevents dismissing authentic, high-quality candidates who only sounded generic

“what's conventional wisdom that you bet against that you have found is actually actually inaccurate”
16:30

“there's no way to answer that question without being genuinely opinionated”
17:00

#interviewing#authenticity#contrarian-thinking

Q&A17:30

"Tell me something that worked out — but not for the reason you thought"

Carbon Health's CPO (a former founder) asks candidates about something that worked out for an unexpected reason, or a good decision that didn't work. The whole aim is teasing out introspection — whether the person reflects on why decisions did or didn't work and updates their model to decide differently next time.

Alternate framing: a good decision that didn't work out
Tests whether the person is reflective about the decisions they've made
Looks for people who incorporate that reflection into their model to decide differently next time

“you did that worked out but not for the reason that you thought it would work”
17:30

#interviewing#introspection#decision-making

Q&A18:00

A limitation you've learned about yourself — and "Do you consider yourself lucky?"

Adobe's chief strategy officer (former Behance founder) asks candidates about something they've learned about themselves that reveals a limitation in how they work, testing whether they stay introspective at their limits rather than blaming others. He also likes asking whether people consider themselves lucky — secure people admit it, and he believes everyone truly is lucky and privileged.

The limitation question tests whether someone stays open and introspective when they hit their limits instead of pointing fingers
The luck question is revealing: insecure people may decline to admit luck
People comfortable with themselves should admit they were lucky
His view: we're all very lucky and privileged

“I like asking about something people have learned about themselves that reveal the limitation in how they work”
18:00

“do you consider yourself lucky I think it's a fascinating question”
18:30

#interviewing#introspection#luck

Q&A19:00

"Tell me about a time you delivered something impactful"

Notion's head of growth asks candidates about a time they delivered something impactful, specifically to hear how they define impact and what it means to them. For a growth practitioner, a good answer shows intrinsic motivation about having an impact on the business.

The point is to learn how the candidate defines impact
A good growth answer shows intrinsic motivation to impact the business

“I'm looking for someone to help me understand how they Define imp and what it means to them”
19:00

“I think a good answer for growth practitioner is intrinsic motivation about having an impact on the business”
19:00

#interviewing#impact#growth

Q&A19:30

The reference-call question that can't be dodged

Intercom's CPO shares a reference-call tactic for when you already want to hire someone. Since references are always the candidate's favorite managers, he asks what feedback they'd be giving this person in their first performance review — a question the referee can't dodge, forcing genuinely useful signal.

Used on reference calls after you've decided you want to hire someone
References are always the best people the candidate worked with, so they inflate
Asking about first-performance-review feedback forces an honest answer they can't dodge

“this question is what feedback will I be giving this person in their first performance review it's an amazing question because the person can't Dodge…”
19:30

#interviewing#reference-checks#hiring

Key ideas

Frameworks in this episode

The Ambiguity Navigation Rubric

The Compelled Test (Storytelling as Product Signal)

The Constrained Self-Awareness Probe

The First Performance Review Reference Call

The Hardest Thing Test (Calibrating Difficulty and Agency)

The Hogwash Question (Breaking the Interview Mindset)

The Introspection Probe (Decoupling Decisions from Outcomes)

The Proudest Work Question (Taste Triangulation)

The Teleportation Device Test (Finding the Important Question)

People & resources mentioned

People · 18

Resources · 38

Insights & moments

❝Story· 1

The teleportation device: which two questions would you ask?

?Q&A· 14

"To what do you attribute your success?" — and you can't say luck

"What's the hardest thing you've ever done?"

"Describe a time you were part of a controversial product decision"

"Tell me what work you are most proud of"

How candidates navigate ambiguity

"What unfair secrets have you learned to improve a team's velocity?"

"Fast forward three years — what's different about you?"

"What would your siblings say about you?"

"Tell me about a time something went wrong"

"What does everyone take for granted that you think is hogwash?"

"Tell me something that worked out — but not for the reason you thought"

A limitation you've learned about yourself — and "Do you consider yourself lucky?"

"Tell me about a time you delivered something impactful"

The reference-call question that can't be dodged

Story· 1

Q&A· 14