"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.

Work-related:

• 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 lighting you up outside of work?
• What's an ideal Sunday morning for you?
• 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?
• If you didn't know the day you were born, how old would you think you are?
• What's something about you that you think is a good quality, but others would disagree?
• What's something random or improbable that happened in the past that had a major impact on your life?

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?

Questions for doing a "self-review":

• What are the recent wins?
• What are the things I am bad at that I AM accepting and not working on?
• What are the things I am bad at that I am NOT accepting and working on?
• What are the things in my life I am no longer willing to tolerate​ and plan to start working on?

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?
• Topics like risk, greed, and fear are not the kind of things that we can learn and master as a society such as agriculture. Some lessons have to be experienced firsthand before they can be understood. (Michael Batnik)
  • Instead of asking - why do you believe that?
  • Ask - “What have you experienced that I haven't that makes you believe what you do?”
  • Ask - “Would I think the same thing if I experienced what you have?

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