1. Is it more important to move fast and get it done, or to take your time and do it right?
2. Can you describe an example of when you helped your team move faster?
3. Describe a time when the organization you were working for went too fast and it was a problem. How did you feel about this? (They should say they loved going fast even when things went wrong.)
4. How do you prioritize building processes and systems versus shipping against your goals and deadlines?
5. Describe a time when you over-delivered against what was expected of you. Why did you want it so badly?
6. What are some projects you’ve done in the past that you came up with yourself? If it didn’t get implemented, why could you not convince your boss at the time?
7. What do you consider to be your best idea at work, and what obstacles did you overcome to make it happen?
8. Three years from now, what new things will you have learned, who do you want to have added to your network? How will this job help you achieve this?
9. If you were to get this role, what would be your biggest challenge and how would you approach it?
10. We are resource-constrained and things are really ambiguous here, is that what you want for yourself?
11. Describe a time when your boss changed plans really quickly. How did that make you feel?
12. Describe a time when things were changing really quickly. What was the environment like for you? (Notice if they use negative words or positive words.)
13. Describe a time when you had to change your plans suddenly. How did you communicate this with other people?
14. Who’s the most difficult person you’ve worked with?
15. Tell me about a time when you loved your work. What did you enjoy about it?
16. Describe a time when you became consumed with what you were working on. How did you deal with it?
17. Describe something you created, either in work or outside of work, that you are proud of.
18. When was the last time you were working on something and looked up at the clock only to be shocked at how much time had passed? What were you working on, and why were you so absorbed by it?
19. Tell me about a niche product or something for your hobbies or passions that you’re extremely opinionated about and why.
20. What’s the most recent thing you learned about yourself at work? How did you learn it? Why?
21. Walk me through your last few jobs. What did you learn and why did you leave each?
22. What do you want out of your next job that you aren’t getting now?
23. How long can you see yourself being here? What’s next for you?
24. What was the highest performing team you’ve ever worked on? Why was it so high performing? What was your role?
25. What is your superpower? What is the one thing you do better than most others in your profession?
26. What do your coworkers tend to respect and admire most about your work?
27. What do you consider your natural gifts, and what are the things you’ve worked hardest to get good at?
28. Who have you learned the most from in your career? What did you learn?
29. How do you push the boundaries and limits of what you do?
30. What advice would you give to someone starting new in your profession? What are the best things to spend time learning and doing, and what’s a waste of time?
31. What are you most proud of in your career so far?
32. If we hired you today, who would immediately want to join us?
33. Can you name a time when you recruited someone to a company you were working on?
34. Who are the three most exceptional people you’ve ever worked with and what made them so exceptional? Do you think you could convince them to join you here if we hired you?