“The best discoveries in life come not from finding the right answers, but from asking the right questions.”

"Ask a better question, get a better answer."

- Shaan Puri

Inspired by Shaan Puri's idea of being a "question collector", I started doing the same and now keep a running list of questions that I find valuable.

  • Instead of: When will this be done?
    • When would you be surprised if we didn't have this done by?
    • When would you be surprised by it being done?
    • Okay, great. So best case scenario, what are you thinking?
  • When someone explains a long, complex plan:
    • All that sounds really hard. What would be easy?
  • When managing someone:
    • What's on your mind?
    • What's a conversation you've been avoiding?

Small Talk/Getting to know someone:
  • What's on your unofficial resume?
  • Who are your role models and why?
  • What's an ideal Sunday morning for you?
  • What's lighting you up outside of work?
  • What are you most excited about currently?
  • If you had another career, what would it be?
  • What's something you're happy to overspend on?
  • What's your favorite book you've read recently?
  • What is a risk you took that changed your life?
  • You look happy! What were you doing right before this?
  • What's the nicest thing someone's ever said about you?
  • What's the meanest thing someone's ever said about you?
  • Tell me about your friends and why are they your friends.
  • What's an encounter with a stranger you will never forget?
  • What is something about you that people tend to get wrong?
  • When was the last time you did something for the first time?
  • What is something you'd whisper in the ear of your younger self?
  • If you could have any job in the world, what would it be and why?
  • If you could move anywhere in the world, where would it be and why?
  • You got a little pep in your step today, what'd you have for breakfast?

Questions I ask myself often:
  • Who needs my help?
  • What are my anti-goals?
  • Am I playing a stupid game?
  • Is this the beginning, or is this the end?
  • If I could only work two hours today but still wanted today to be a huge success, what would I do in those two hours?

When I interview someone:
  • What is your superpower?
  • What's the hardest thing you've ever done?
  • What did you fail at in the last 12 months?
  • What's the best advice you've ever received?
  • What question am I not asking you that you want me to?
  • What could you give a 5-minute presentation on with no prep?
  • What one habit has made a crucial difference in your success?
  • What do you think we are doing wrong as a company right now?
  • What's something that everyone takes for granted that you think is hogwash?
  • What's something you have changed your mind on over the last decade/recently?
  • Tell me about a time when you needed to disagree with your manager or fight for a position against higher leadership.

When someone offers an opinion or belief or does what they do, the best questions to ask people (in a non-judgemental way):
  • Why do you do that?
  • Why do you think that?