Questions to Get to Know Someone: 40 That Don't Feel Forced

You meet someone and want to know more about them than their job title. But "What is your biggest fear?" ten minutes in feels like a test. The question isn't wrong. The timing is.

In short

You get to know someone with questions that fit the moment. Start light, follow up on what the other person says and only go deeper once they share something personal themselves. Answer your own questions too. Without that, a list of questions feels like a job interview.

Why most question lists fall flat

Most lists online put light and heavy questions side by side. On paper they look great. In a real conversation, a deep question too early makes people careful. A conversation only gets deeper once there is a bit of trust. So the order matters more than the question.

The staircase: light, personal, deep

Think of three steps. You only go up a step when the other person comes along.

Step 1: light (the situation, the here and now)

1. How do you know the people here?
2. What brought you here today?
3. Do you come here often?
4. What's keeping you busy lately?
5. What did you do this weekend?
6. Where do you live, and do you like it?
7. Anything nice coming up?
8. What do you like to eat when you don't have to cook?
9. What are you watching at the moment?
10. Are you a morning person?

Step 2: personal (choices and preferences)

11. How did you end up in your line of work?
12. What do you enjoy most about it?
13. What can you spend hours on without noticing?
14. What did you learn recently?
15. Which place would you still love to see?
16. What do you do when you really want to unwind?
17. Who has influenced you most in the last few years?
18. What would you do with a free month?
19. What are you secretly good at?
20. What do you miss from when you were younger?

Step 3: deep (what someone cares about)

21. What are you proud of lately?
22. What would you do differently if you could start again?
23. What gives you energy, and what drains it?
24. When did you last feel really at home somewhere?
25. What do you find hard to ask other people?
26. Which decision changed your life the most?
27. What do you still want to be doing in five years?
28. What have you changed your mind about?
29. What does friendship mean to you?
30. What are you actually worried about?

Questions by situation

A colleague you don't know yet

31. What does a good workday look like for you?
32. Where did you work before this?
33. What would you change here if you could?

A new friendship

34. What do you usually do on a free Sunday?
35. How did you meet your closest friends?
36. What have you always wanted to try?

A date, or someone you want to know better

37. What makes you happy on an ordinary Tuesday?
38. What's the nicest compliment you've ever had?
39. What do you value in the people around you?
40. What do very few people know about you?

The question is only half of it

A good question gets you an answer. What you do next decides whether it becomes a conversation. Pick one word from the answer and ask about that. If someone says "I just moved", don't jump to their job. Ask: "Why there?" I wrote more about picking up those hooks in What to do with what a stranger just said.

Give something of yourself

Asking without giving back feels like an interrogation. A simple rule: ask a question, then answer it yourself in a sentence or two. The other person will share more easily. More on this in Self-expression in conversation.

When can you go deeper?

Watch what the other person does. If they tell you something personal without being asked, that's an invitation. If the answers stay short, stay a step lower. Nothing wrong with that. Light conversations count too.

When it goes quiet

Use the Conversation Compass: 30 topics to fall back on when you don't know what to say next.

Out of questions altogether? 25 angles for any topic gives you new directions from whatever you were just talking about.

Practise it

In the course Talking with People you practise asking questions, following up and deepening a conversation, one step at a time. The first module is free.