Unusual Questions That May Help You Hire The Best Candidate

Published in Jan 2, 2020

Hiring is definitely one of the most important challenges startup founders face. Throughout this process, differentiating between candidates (especially when there are many suitable ones) can be a daunting task. One that gets even harder during the interview phase, when maximizing what you can learn about candidates and avoid being deceived by memorized answers can prove very beneficial to the quest of finding the right person. To this aim, we recommend that you consider using some of these unexpected and thought-provoking questions in your next interview:

  • Among the people you’ve worked with, who do you admire and why? (Jules Walter, Product Lead, Slack)
  • What’s one part of your previous company’s culture that you hope to bring to your next one? What one part do you hope to not find? (Ben Kamens, Founder and CEO, Spring Discovery)
  • What are you really good at, but never want to do anymore? (Bryan Mason, Chief Business Officer, VSCO)
  • When was the last time you changed your mind about something important? (Sarah Fetter, Managing Director, East Rock Capital)
  • What’s one misconception your coworkers have about you? (Sam Gerstenzang, Co-Founder, Umbrella)
  • What are 10 ways to speed up Domino’s pizza delivery? (Max Branzburg, Director of Product, Coinbase)
  • Why shouldn’t we hire you? (Romy Macasieb, VP of Product, Walker & Company)
  • Teach me something. (Nathalie McGrath, VP of People, Coinbase)
  • What have I not asked you that I should have? (Liza Hausman, VP of Industry Marketing, Houzz)


These unusual questions were selected from this article at First Round Review, the blog of First Round VC firm. Take a look at it, to understand the reasoning behind the questions above, and discover many more interesting ones.