36 questions to ask that tell you who someone is beyond their job

Every time I hear the dreaded “So, tell me about yourself”, I feel stumped. I know I am more than the job title and educational degree that my brain is instinctively rushing to, but it also feels extremely awkward and abrupt to suddenly launch into my fear of death or my all-time favourite book (Tuesdays with Morrie by Mitch Albom, if you care).

It saddens me that we can spend hours—even years—sitting alongside colleagues or peers, knowing every detail about their career trajectory but nothing about who they are when the day ends and they leave their desks. That said, there’s no reason to suddenly force a deep, soul-searching bond with that co-worker who has been perfectly comfortable with maintaining a shared silence for years. But often, there are deeper details that we don’t know even about the people closest to us. Think about it: how much do you know about your own parents’ favourite childhood memories or the dreams they silently let go of?

To avoid reducing people to their jobs, we’ve put together a list of questions to ask that demand more than a simple ‘yes’ or ‘no’. Whether you’re sitting across from someone you just met or somebody you have known for years, here are 36 open-ended questions to ask that allow you to really see the person in front of you.

1. If you could relive any moment in your life, which would it be?
2. Who is someone who has had a deep influence on you, and in what way?
3. If you had complete free will for a day, how would you spend it?
4. If the world were ending, who would you want to spend your last day with?
5. How do you prefer to cope when you have a bad day?
6. What’s a book, TV show or movie that you think everybody must read or watch, and why?
7. If you could donate significant money towards any cause, which would it be?
8. When do you feel most like yourself?
9. What do you secretly wish people would ask you about more often?
10. What role do you usually play in a group? Are you satisfied with that role?
11. Could you describe yourself while you’re under pressure?
12. What’s something you believe you are good at?
13. Who is a fictional character you most identify with, and in what way?
14. When have you felt the most proud of yourself?
15. What might people not guess about you just by looking at you?
16. Can you describe the conditions in which you thrive the best?
17. Do you believe you were born in the correct generation? If not, which generation do you most identify with, and why?
18. What kind of energy do you hope people feel from you after you leave a room?
19. If fear didn’t factor into your decisions, what would you aspire for first?
20. What’s your view on love?
21. Do routines feel more reassuring or restricting to you? Why?
22. If you could live anywhere in the world, where would you choose to live?
23. What’s the best advice you’ve come across?
24. If you could dedicate a significant amount of time towards learning something new, what would it be?
25. To what extent do you think people’s perceptions of you are accurate?
26. What’s something that you wish people would pay attention to more?
27. When do you like yourself the most?
28. What’s your greatest fear?
29. If you could hold a debate on any topic, what would it be and which side would you represent?
30. When you’re in a group setting, do you find yourself speaking up naturally or holding space for others to take the lead?
31. Who is someone you look up to, and why?
32. What’s a compliment you receive often?
33. How would you describe your emotional reflex during difficult times?
34. Is there something you would like to change about yourself, and why?
35. What song lyrics do you most identify with?
36. Can you describe the dream version of yourself? How similar do you believe you are to them currently?