Favorite Interview Questions


The interview questions are a mix of probing and unexpected, other go deeper on typical behavioral interview questions.

Unpacking Their Career Path

  • What do you want to do differently in your next job?
  • Instacart, CEO and Co-Founder Max Mullen explains:
    • “I find that the best answers highlight what they’re running toward, rather than what they’re running from in their current job. If they launch into what they don’t like about their boss or current company, that tells you a lot. It tests whether they’re a positive person and how they handle adversity.”
  • 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?
    • Kevin Weil, Libra co-creator and VP for Calibra at Facebook:
      • “I love this question because it helps me understand how they think through big decisions”
      • This helps to find underlying motivations and career goals

Discover Motivations

  • Among the people you've worked with, who do you admire and why?
    • Jules Walter, angel investor and product lead at Youtube says this question pulls the candidate's values in a subtle and honest way.
  • What’s something great about your current or previous job? Why?
  • What motivates you to work?

Fit For the Role

  • What are you really good at, but never want to do anymore?
    • Business man @VSCO, Bryan Mason, explains that gets candidates to:
      • Reflect on their learnings;
      • Test ability to speak with humility about being "good"
  • What’s the difference between someone who’s great in your role versus someone who’s outstanding?
    • From Matt Humphrey, Lending Home's CEO.
    • 🖍️

      I've used this question but structured it between "What makes, good vs great", but this should help the candidate show what are their standards

  • How did you prepare for this job interview?
  • What do you believe you can achieve with us personally or professionally that you can't anywhere else in the world?
  • It's December 5th, 2021. What impact on the business have you made in the year since you’ve joined?
    • PatientPing, CEO Jay Desai: "I've found that it provides visibility into how long the candidate thinks things should take."
  • When was the last time you changed your mind about something important?
  • If I were to go and speak to people who don't think very highly of you, what would they say?
  • What’s one critical piece of feedback you’ve received that was really difficult to hear?
    • Why was it difficult?
  • What was the last thing you nerded out on?
  • Teach me something. (5 minute communication method)
  • If you were to take over as CEO of your current company tomorrow, and had to increase your company's current rate of growth, what three areas you would invest in?
  • What have I not asked you that I should have?