?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…”
#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…”
#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”
#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…”
“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”
#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”
#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”
#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”
“tell me about the diversity equity inclusion and belonging initiatives that you've recently”
#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…”
#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”
#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”
“there's no way to answer that question without being genuinely opinionated”
#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”
#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”
“do you consider yourself lucky I think it's a fascinating question”
#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”
“I think a good answer for growth practitioner is intrinsic motivation about having an impact on the business”
#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…”
#interviewing#reference-checks#hiring