I’ve been running an experiment where I ask people at least one of the following questions to understand their thinking and personality better. I feel like a lot of time is wasted on small talk and discussing work, so I encourage you to skip all of that and see what interesting conversations come out of these questions!

If you were going to be frozen tomorrow for a one-way 1000-year interstellar voyage, what would you most want to communicate (and to whom) before you leave?

What do you think you’re most likely to regret on your deathbed?

What do you miss most about your past that could be recreated today?

What’s the most important thing to remember daily that you haven’t been able to?

What help could you most use that you haven’t asked for?

What is your one piece of advice to everyone here?

What was the last thing you fell in love with?

When was the last time you felt unbounded optimism?

Who was the last person you felt inspired by?

What simple thing still blows your mind?

What sparked your curiosity in whatever you’re most curious about now?

What’s the most useful concept you have that doesn’t have a name?

What’s something you believe but can’t defend?

What taste do you have that most people don’t have, where does it come from, and how has it helped you?

What is your most radical belief?

Do you think it’s more important to follow the “written” rules or the “unwritten” rules? What is one unwritten rule that you’ve learned?

What is the most significant thing you’ve changed your mind on in the last year? Why did you change your mind about it?

Which fictional character would be the most boring to meet in real life?

What’s the closest thing to real magic?

If you could know the absolute and total truth to one question, what question would you ask?

Which question can you ask to find out the most about a person?

What do you want your epitaph to be?

There are two types of people in this world. What are the two types?

What is something you are certain you’ll never experience?

Who is/was your most interesting friend?

What small gesture from a stranger made a big impact on you?

If you had a clock that would countdown to any one event of your choosing, what event would you want it to count down?

What are three of the most significant numbers in your life?

Which of your personality traits has been the most useful?

Imagine you have a closet full of robots at the ready. Which of your various obligations would you assign to a robot? Which tasks and activities would you keep to yourself, because you enjoy them too much to delegate them to even a robot who is better than you?

What is the best measurement of how an idea is absorbed into culture?

Do you think you’re undervalued as a person? If so, why?

Why are some people so addictive?