Getting to Know You

Asking Questions of Others

Getting to Know You

The following questions are to be asked when you want to get to know someone else more personally or deeply. This could be a friend, a member of a small group, or a work team. Give a few a try.

Check out the page of questions FOR COUPLES: Getting to Know You Deeper.

Try to avoid, “How are you doing?” This is such a bland way to interact with others. We are so programmed to give well-rehearsed answers, such as “Great.” or “Fine” and we keep on moving. Stop and get to know someone. And then LISTEN. [By the way, FINE may simply mean: Feelings Inside Not Exposed.]

GETTING STARTED - SURFACE

  1. Tell me about (fill in the blank). [This is a great way to get a conversation started. If you ask, “How was your day?” You might get a “Fine!” Not with “Tell me about your day.” ]

  2. Tell me about your childhood. (David Brooks)

  3. What are you learning? (or have been learning or reading?)

  4. What's the best thing you've ever made or created?

  5. What's something you're looking forward to in the next few months?

  6. If you could only eat one thing for the rest of your life, what would it be?

  7. What's the best thing about your job?

  8. What's one thing you're proud of that you've accomplished?

  9. What's the best piece of advice you've ever received?

  10. What's a unique experience you've had that you'll never forget?

  11. If you could have any superpower, what would it be?

  12. What's the best thing that's happened to you this week?

  13. What's the most interesting place you've ever been to?

  14. How do you like to spend your free time?

  15. What's something you've learned recently that surprised you?

  16. If you could have dinner with any historical figure, who would it be?

  17. What's something you've always wanted to try but haven't yet?

  18. Who is your hero? (Vanessa Van Edwards)

  19. What fuels or reenergizes you? What do you absolutely love to do where you lose time?

  20. What is the strangest thing you know too much of?

  21. If you could change your name, what would you change it to and why?

  22. Where is the most interesting place you've been?

  23. Who would you like to meet for dinner and what two questions would you ask and why?

  24. To what point in history would you like to time travel and what would you hope to witness?

  25. If you suddenly became a master at woodworking, what would you make?

  26. “What if” questions - here are some samples

    1. What if you could live for 200 years?

    2. What if you could stop time whenever you wanted to?

    3. What if you could be any animal?

    4. What if you used a public toilet and discovered there was no paper?

    5. What if you had to choose between great wealth or great wisdom?

  27. “Would you rather” questions - here are some samples

    1. Would you rather team up with Wonder Woman or Captain Marvel?

    2. Would you rather be forced to sing along or dance to every single song you hear?

    3. Would you rather lose your sight or your memories?

    4. Would you rather give up air conditioning and heating for the rest of your life or give up the Internet for the rest of your life?

    5. Would you rather go back to the past and meet your loved ones who passed away or go to the future to meet your children or grandchildren-to-be?

GETTING DEEPER - MORE PERSONAL

  1. What’s your story? OR

  2. What’s a part of your story that doesn’t often get told?

  3. What is your favorite unimportant thing about you? (David Brooks)

  4. What is it about you that no one knows about? (Peter Block)

  5. How are you thinking (instead of how are you feeling)?

  6. What life events, people, or encounters shaped your personality and made you who you are?

  7. What gets you fired up?

  8. What is THE one question that you would ask God?

  9. Describe the kind of person with whom you would share your most important password.

  10. What is a community to which you belong? Reflect on the footprint that you have left. (Yale)

  11. If you have free time, what might I find you doing and where?

  12. What job would you be terrible at?

  13. What book, TV, or movie character is most like you, OR are you most like? (Vanessa Van Edwards)

  14. What’s a small thing that makes your day better?

  15. What’s the most annoying habit other people have?

  16. What do you want to be remembered for?

  17. If the next five years is a chapter in your life, what is this chapter about? (David Brooks)

  18. If we met a year from now, what would we be celebrating? (David Brooks)

  19. What is the proudest moment of your life? (Vanessa Van Edwards)

  20. What’s something a ton of people are obsessed with but you just don’t get the point?

  21. What website do you visit most often?

  22. What is something you will never do again?

  23. If you could make 1 rule everyone has to follow, what would it be?

  24. What is your favorite smell?

  25. What can you NOT get right, no matter how many times you try?

  26. What are you really good at...but a little embarrassed you're good at it?

  27. What keeps you up at night?

  28. Who inspires you to be better?

  29. If you could turn any activity into an Olympic sport, what would you have a good chance at winning gold?

  30. What do you regret not doing or starting when you were younger?’

REFLECTING ON LIFE

  1. What was the highlight of your day (or week)?

  2. What does this remind you of”- it opens the door for useful conversations

  3. What was your dream job growing up?

  4. Why did you choose your profession?

  5. What would you change about how you were raised?

  6. What’s one childhood memory that affects you the most today?

  7. What is one of the most defining moments of your life?

  8. What lessons have you learned from a regret in your life?

  9. What book has influenced you the most?

  10. What is the book (or books) you’ve given most as a gift, and why? Or what are one to three books that have greatly influenced your life? (Ferris)

  11. What would you tell your teenage self if you could go back in time?

  12. How surprised would your younger self be about who you are or how you live today?

  13. What would you do if you weren’t afraid? (David Brooks)

  14. Reflect on a time in the last few years when you felt genuine excitement learning about something. (Yale)

  15. In the last five years, what have you become better at saying no to? What new realizations and/or approaches helped? (Ferris)

  16. In the last five years, what new belief, behavior, or habit has most improved your life? (Ferris)

REVEALING COMPLEXITIES

  1. What have you created that you are most proud of?

  2. What is an unusual habit or an absurd thing that you love? (Ferris)

  3. What is it about you that no one knows that you would like to have said at your funeral? 

  4. What in your life currently makes you feel the most fulfilled?

  5. What is not yet accomplished in your life that you thought would have been?

  6. How exhausting is it when you fear that someone might find out something about who that no one knows?

  7. What is your attitude toward failure & mistakes?

  8. How would you use an undo button for one life event & how would you hope it changed the present?

  9. What would you do if you knew you wouldn't fail?

  10. How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours? (Ferris)

  11. When should you have spoken up and what could you have said that would have changed that moment?

  12. What possibly surprising things do you think about when you are completely alone?

  13. What is one thing you're glad you tried but would never do again?

  14. What question do you always want to ask people but don't have the courage to ask?

  15. Who's your go-to band or artist when you can't decide on something to listen to?

  16. In what areas of life has your perspective shifted from what you used to think to what you now think & what was the catalyst for each shift?

  17. If I really knew you, what would I know about you?

  18. How do think your friends describe you when you’re not with them?

  19. Describe the door to the inner, secret room that no one has ever been allowed to enter.

  20. When you feel overwhelmed or unfocused, what do you do? (Ferris)

  21. What's something you hated about yourself as a kid or teenager that you now consider a strength? (From a tweet)

  22. Tell me something that’s TRUE that almost no one agrees with you on (Thiel).

  23. What commitment have you made that you no longer believe in? (Peter Block)

  24. What skill do you currently hold in exile? What talent do you have that you aren’t using? (Peter Block)

TEACHING/LEADING SMALL GROUPS

  1. What surprised you today, and why?

  2. What’s the most important thing you learned today? Why do you think so?

  3. What do you want to learn more about, and why?

  4. When were you the most creative, and why do you think that is?

  5. What made you curious today? How does learning feel different when you’re curious?

  6. When were you at your best today, and why?

  7. (Assuming we were studying the same thing and you could decide and have access to anything), where would you start tomorrow? Why?

  8. What are your next right steps that you could take? What might that look like? 

  9. What can/should you do with what you know/learned?