Interviewing Guide

Here are some questions for you to consider in your interview process:

• "Walk me through a time you had to solve a highly ambiguous technical problem. How did you start, and what did you learn?"

• "Can you explain [a core concept] from your field in simple terms to someone outside your domain?"

• "Tell me about a time your assumptions were wrong during R&D. What did you do?

• "Here’s a real challenge we’re facing. How would you approach it?" (case-style prompt)

• "Describe a project where things kept going wrong. What kept you going?"

• "What’s the hardest thing you've ever built, and what made it hard?"

• "Tell me about a time when the data or results said 'stop,' but you pushed forward anyway. Why?"

• "How do you stay sharp and up-to-date in your field?"

• "What’s a time you had to unlearn something or change your mind based on new evidence?"

• "How do you approach learning in a field you're unfamiliar with?"

• "Tell me about a time you had to work closely with someone from a very different technical background. What worked — or didn’t?"

• "Have you ever had a conflict over a technical direction? How did you handle it?"

• "Why this company, and why now?"

• "What excites you most about working on hard problems that may take years to solve?"

• "If you had funding to work on any tough tech challenge for 5 years, what would you choose?"

• "How do you decide when to ship vs. keep iterating?"

• "Have you ever worked under a leader or founder you disagreed with? What did you learn?"

• "When have you failed to convince others of an idea that you believed was right?"

• “What are your career goals?”

• “What are you not good at or not interested in doing professionally?”

• “Who were your last five bosses, and how would they each rate your performance on a 1–10 scale?”

• “Tell me about the hardest problem you’ve ever solved. What made it hard?”

• “Walk me through how you approached [specific past project]. What would you change if you did it again?”

• “How do you make decisions when there’s no clear right answer?”

• “What are you most proud of in your career so far? Why?”

• “Tell me about a time when you exceeded expectations. What drove you?”

• “What’s a professional failure you’ve had, and what did you learn from it?”

• “What’s the most constructive feedback you’ve received — and how did you respond?”

• “What’s a skill or area you’ve had to develop that didn’t come naturally to you?”

• “Why this role? Why now?”

• “What’s the most energizing part of your work?”

• “What kind of work environment makes you do your best work?”

• “If you didn’t need the money, what would you spend your time building or solving?”

• “Tell me about a time you had a conflict with a teammate. How did you handle it?”

• “How do you earn trust quickly on a new team?”

• “What kind of people do you find it hardest to work with — and how do you deal with that?”

• “Describe a time you led others through uncertainty or change. What did you learn?”

• “What’s a decision you made that wasn’t popular — but you believed in?”

• “How do you scale yourself as a leader or contributor?”

• “What are your personal values, and how do they show up in your work?”

• “What kind of culture brings out your best? What kills your motivation?”

• “How do you react when priorities shift or the mission gets questioned?”

• “What should I have asked you that I didn’t?”

• “If you get this job, what do you hope to accomplish in your first year?”

• “What’s the legacy you want to leave behind in your work?”