Here’s a collection of questions I often ask others and myself.

10 Questions to ask others

1. How do you decide what to work on next?
2. What would you write on a gigantic billboard?
3. You have a Time-Machine which you can only use once, would you go in past or future?
4. What is something people always misunderstand about you?
5. What are you excited or curious about these days?
6. If you were asked to give a TED Talk, what topic would you talk about?
7. What advice would you give to your 18 year old self?
8. What is your favourite documentary?
9. What is something you believe that other people think is insane?
10. What is the best or most worthwhile investment you’ve made? Could be an investment of money, time, energy, or other resource. How did you decide to make the investment?

10 Ice breaking questions

1. What would you eat if you could only eat one food for the rest of your life?
2. If you could rename yourself, what new name would you choose, and why?
3. Describe something that’s made you smile today.
4. Which book did you read in college or high school that was actually interesting enough that you still think or talk about it sometimes?
5. If you did not have to sleep, how would you spend the extra 8 hours?
6. What question do you wish people would ask you?
7. What is something you didn’t like but you are glad happened?
8. Imagine you could devote a year to researching someone’s biography. Who would your subject be?
9. What’s something new you’ve learned about yourself in the last three months?
10. Have you ever quit doing something that you used to be really passionate about? Do you regret it? Or are you happy you quit? Either way: Do you think you’ll ever take it up again?

10 questions to help you think clearly:

1. Is this making me a better person?
2. What is your idea of happiness?
3. What is it that I can think of, read, watch, listen and talk about for hours on end without realizing it?
4. Will this become a good story for my grandchildren?
5. Don’t ask “What’s going to change in the next 10 years? Ask “What’s not going to change in the next 10 years?
6. How much of your money is allocated towards greatness?
7. Ask yourself at every moment, ‘Is this necessary?’
8. What matters most to me after family, food & a roof over my head?
9. Do I wake up in the morning looking forward to work?
10. When was the last time I tried something new for the first time?

10 questions to ask ourselves:

1. 1If I had 30M in the bank, how would my day-to-day change?
2. 2/ What is 1 thing I will do differently tomorrow?
3. Am I doing/not doing this out of fear?
4. What would I do if there was no risk attached?
5. What would this look like if it was fun?
6. What am I most proud of in my life?
7. What are the big things/little things I’m grateful for today?
8. What would it take to snap me out of my bad mood immediately?
9. How can I learn from this experience?
10. What’s the first thing you think of when you wake up most days?

10 questions to ask during interviews (Podcasts, Zoom calls)

1. If I interviewed your siblings and 3 best friends and asked them to describe you, what would they tell me?
2. “Tell me about a time when . . .”
3. “Tell me the story of . . . [how you came to major in X, how you met so-and-so, etc.]”
4. What would you write on a gigantic billboard?
5. “Tell me about the day [or moment or time when . . .”
6. What’s a question you wished people asked you often?
7. Tell me about the day you realized • • •
8. “What were the steps that got you to ?”
9. “Describe the conversation when . . .”
10. What do you own, and why?

Feel free to add more questions in the comments. I’ll be adding more questions as I go.

Remember. Asking the right question is a skill. Asking the right question at a right time is a superpower.