The First Round Review team reached out to some of the smartest and most thoughtful operators in our network to pose a simple question: What’s your favorite interview question and why? What follows is an exclusive list of interview questions, sent to us by the sharpest folks we’ve met or just outright admire. We hope this collection serves as a rich jumping off point that you can leverage as you design your own interview process, whether you’re building it from scratch or looking to give it a refresh as you double-down on hiring.

For more context on who recommended each question and what they look for in a candidate's answer, be sure to check out the Review article in full. We also shared 10 new bonus questions with subscribers to the First Round Review newsletter—sign up here if you haven't already for exclusive content and the best advice in tech, in your inbox weekly.


  1. What do you want to do differently in your next role?
  2. Imagine yourself in three years. What do you hope will be different about you then compared to now?
  3. For the last few companies you've been at, take me through: (i) When you left, why did you leave? (ii) When you joined the next one, why did you choose it?
  4. Among the people you've worked with, who do you admire and why?
  5. Tell me about a time you took unexpected initiative. Follow-up: Can you tell me about another?
  6. What’s something great about your current or previous job? Why?
  7. What motivates you to work?
  8. Looking back on the last five years of your career, what’s the highlight?
  9. What are you really good at, but never want to do anymore?
  10. What’s the difference between someone who’s great in your role versus someone who’s outstanding?
  11. How did you prepare for this interview?
  12. What do you believe you can achieve with us personally or professionally that you can't anywhere else in the world?
  13. What are the three most important characteristics of this function? How would you stack rank yourself from strongest to least developed among these traits?
  14. Tell me about your ideal next role. What characteristics does it have from a responsibility, team, and company culture perspective? What characteristics does it not have?
  15. It's September 5, 2020. What impact on the business have you made in the year since you’ve joined?