50 Virtual Coffee Chat Questions That Actually Start Conversations

A virtual coffee chat fails in one of two ways. Either it turns into a status update ("so what are you working on?") or it dies after three minutes because neither person knows what to ask. The fix for both is the same: start with one good question and let it go wherever it goes.

Here are 50 that work, sorted by theme so you can pick the one that fits.

How to run a virtual coffee chat

• Keep it to two or three people. Four is a meeting.
• Book 20 minutes. Long enough to get past small talk, short enough that nobody dreads it.
• Pick one question in advance. Send it in the invite so the quieter person has time to think.
• No agenda, no notes, no action items. The absence of output is the point.
• Pair across teams. The best chats are between people who would never otherwise talk.

If you would rather have the pairing and the opening question handled for you, Virtual Coffee does both.

The questions

Getting to know you

1. What is something you are good at that has nothing to do with your job?
2. Where did you grow up, and do you still have ties there?
3. What did you want to be when you were ten?
4. What is a small daily ritual you would not give up?
5. How did you end up in this line of work?
6. What is one thing most colleagues do not know about you?
7. What are you reading, watching, or listening to right now?
8. What is a nickname you have had, and where did it come from?

Work and career

9. What is the best job you ever had, and what made it good?
10. What is a piece of work you are quietly proud of?
11. What is one thing about your role you wish other teams understood?
12. Who has had the biggest influence on how you work?
13. What skill are you trying to build this year?
14. What does a genuinely good workday look like for you?
15. What is the most useful thing you learned from a failure?
16. If you could swap jobs with anyone at this company for a day, who?

Hobbies and weekends

17. What did you do last weekend that you would do again?
18. What hobby have you kept the longest?
19. Is there something you collect, on purpose or by accident?
20. What is a skill you learned purely for fun?
21. What do you do when you need to switch your brain off?
22. What is the last thing you made with your hands?
23. What is a hobby you have always wanted to try but have not?
24. Are you an early-start weekend person or a sleep-in weekend person?

Food and travel

25. What is a dish you could eat every week without getting bored?
26. What is the best meal you have had while travelling?
27. What is a food from your childhood that still means something to you?
28. Where is a place you have been that surprised you?
29. What is on your travel list for the next few years?
30. Do you have a go-to recipe when people come over?
31. What is a local spot near you that visitors should know about?
32. What is a food you refused to eat as a kid and love now?

Hypotheticals

33. If you could add one hour to every day, what would you spend it on?
34. If you had to live in another country for a year, where?
35. What would you do with a fully paid month off?
36. If you could master any instrument instantly, which one?
37. What is a job you would try for a week just to see what it is like?
38. If you could have dinner with anyone from history, who and why?
39. What would you teach a class on, if you had to?
40. If you had to keep one object you own and give up the rest, what would it be?

Lighter and funnier

41. What is a strong opinion you hold about something trivial?
42. What is the worst purchase you have ever made?
43. What is a song you know every word to and would rather not admit?
44. What is your most-repeated phrase on video calls?
45. What is something you were weirdly good at as a kid?

A little deeper

46. What is something you have changed your mind about recently?
47. What is a piece of advice you keep coming back to?
48. When did you last feel completely absorbed in something?
49. What is something you are looking forward to that is not work-related?
50. What is one thing that would make this a better place to work for you?

Getting the quiet person talking

Some people freeze on open questions. Two things help. First, answer your own question first, briefly and honestly. It shows the expected length and gives them something to react to. Second, follow up on a detail rather than moving to the next question. "You said you collect maps, how did that start?" is worth more than question 20.

What to avoid

• Anything that sounds like a performance review. "What are your goals?" belongs in a one-on-one with a manager, not here.
• Questions with a correct answer. The goal is a story, not a fact.
• Too many questions. One good one, maybe two. If you got through five, you were interviewing them.
• Going too deep too fast. Save the "a little deeper" set for a second or third chat.

Beyond the chat

Once a few coffee pairs have happened, the team is usually ready for a group format. The Icebreaker Questions activity turns prompts like these into a round for the whole team, and our list of 100 icebreaker questions by situation covers meetings rather than one-on-ones. For the bigger picture, see remote team engagement ideas that don't feel forced.