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Hiring is arguably the highest-leverage activity a leader performs, yet the interview process often falls into a predictable rhythm of rehearsed answers and standard questions. To break through the polish and understand how a candidate truly thinks, operates, and leads, you need better questions.
After interviewing over 100 product leaders and founders from companies like Stripe, Figma, Slack, and Adobe, we have curated a collection of their absolute favorite interview questions. These aren't just logic puzzles; they are psychological instruments designed to reveal self-awareness, grit, strategic thinking, and values.
Whether you are a hiring manager looking to upgrade your script or a candidate preparing for the gauntlet, these questions offer a masterclass in evaluating talent.
Key Takeaways
- Test for self-awareness over bravado: The best candidates can admit to the role luck played in their success and can predict what their siblings—not just their references—would say about them.
- Evaluate process over answers: Use abstract case studies (like a fictional teleportation device) to see if a candidate asks the right questions before jumping to solutions.
- Probe for "Taste": Asking what work a candidate is most proud of reveals their internal quality bar and what they value in a finished product.
- Hack the reference check: Instead of asking for general feedback, ask references what specific constructive criticism you will likely be giving the candidate during their first performance review.
Uncovering Introspection and Self-Awareness
Skill sets can be taught, but character traits like humility and self-awareness are often fixed. Several leaders prioritize questions that strip away the professional veneer to see how a candidate views themselves in the context of the world.
The "No Luck" Rule
Aka Doman (Head of Product at Retool) asks a deceptively simple question with a twist: "To what do you attribute your success—and you can't say luck."
While humble people often default to citing luck, removing that option forces the candidate to reflect on their agency. It reveals how curious they are about their own trajectory and whether they have analyzed the specific actions that got them where they are.
The Sibling Test
Standard questions like "What are your weaknesses?" often invite rehearsed, positive-spin answers. Melum Quan Berwitz (Head of Growth at Deel) bypasses this by asking: "What would your siblings say about you?"
If the candidate doesn't have siblings, she asks about their parents. The goal here is sincerity. A candidate who claims their siblings would call them "organized and the glue of the family" might be performing. A candidate who admits their sister thinks they talk too much shows the kind of self-awareness and vulnerability necessary for a high-growth team.
The "Fast Forward" Visualization
Ben Williams (former VP of Product at Snyk) asks candidates to project themselves three years into the future. He asks, "Fast forward three years. What is different about you then?"
He isn't looking for title aspirations or role changes. He is hunting for signals of a growth mindset. Can the candidate openly identify areas of personal and professional growth they need to tackle? Great product managers are insatiably curious, and that curiosity should extend to their own development.
Assessing Critical Thinking and Ambiguity
In modern tech roles, the playbook is rarely written down. You need candidates who can navigate chaos and structure the unstructured.
The Teleportation Device Case Study
Shishir Mehrotra (CEO of Coda) uses a "coded question test" to evaluate how candidates handle raw ambiguity. He presents a scenario: "A group of scientists has invented a teleportation device. They’ve hired you to bring this to market. What do you do?"
Novice candidates immediately start strategizing. Top-tier candidates stop and ask questions. However, the test has a second layer. Shishir tells them the scientists will only answer two questions before requiring a plan.
"One of my favorite answers came from a product manager who asked: 'Is it safe enough for humans?' and 'Is it more expensive to buy them or to run them (CapEx or OpEx)?' With just those two questions, you can form quadrants. If it's cheap to buy but expensive to run, you place them strategically like airports. If it's cheap to run but expensive to buy, maybe you operate them like public transit."
The specific solution matters less than the method. It tests the ability to identify the "iron triangle" variables that drive a business model.
Navigating the Unknown
J.Z. (Head of Product at Webflow) focuses on behavioral questions regarding ambiguity. She looks for people who don't just survive chaos but structure it. It is not enough to acknowledge that a situation was messy; a strong candidate must demonstrate how they charted a path forward and, crucially, how they sought help. The "lone wolf" hero is rarely the right hire for complex product organizations.
Digging Into Taste, Values, and Judgment
Beyond whether a candidate can do the job, you need to know how they do it. What does "good" look like to them?
Defining Quality
A favorite among leaders like Katie Dill (Stripe), Ki Seok (Linear), and Camille Hearst (Spotify) is simply: "Tell me about the work you are most proud of."
This question is a litmus test for taste and judgment. It reveals what the candidate finds motivating. Do they value pixel-perfect design? Do they value complex engineering challenges? Do they value sheer speed of execution? Their answer aligns their "gravity" with your company's needs.
Handling Controversy
Yuki Yamashita (CPO at Figma) asks candidates to describe a time they were part of a controversial product decision. This tests empathy and perspective-taking. Can the candidate articulate why the conflict existed? Can they represent the opposing viewpoint fairly?
If they can explain the conflict in an even-keeled way, it shows they can navigate the inevitable friction of cross-functional teams without losing their cool or villainizing colleagues.
The "Hogwash" Test
Interviewers often suffer from candidates telling them what they think they want to hear. Nikhil Singhal (VP of Product at Facebook) breaks this dynamic by asking: "What is something everyone takes for granted that you think is essentially hogwash or inaccurate?"
This forces the candidate off-script. There is no safe, generic answer to this question. It requires an opinion. Whether it’s a take on AI, remote work, or agile methodology, this question reveals if a candidate is an authentic, independent thinker or just a parrot of conventional wisdom.
The Ultimate Reference Check Question
Once you have identified a top candidate, the reference call is the final hurdle. However, references are usually hand-picked fans of the candidate. Paul Adams (CPO at Intercom) has a specific question that makes it nearly impossible for a reference to give a fluff answer.
"What feedback will I be giving this person in their first performance review?"
This question is brilliant because it assumes the candidate will get the job and will receive feedback. It forces the reference to be honest about the candidate's growth areas without feeling like they are sabotaging the opportunity. It provides the hiring manager with a roadmap for managing the new hire effectively from day one.
Conclusion
The common thread across all these questions is a move away from skills validation and toward mindset interrogation. Whether it’s asking about a fictional teleportation device or a real-life failure, these leaders are looking for the "how" and the "why" rather than just the "what."
If you are hiring, try swapping out one of your standard behavioral questions for the "Hogwash" test or the "Sibling" question. If you are interviewing, prepare to discuss your failures and your unfinished growth areas as confidently as you discuss your wins.
