Coffee chat questions: 30 to ask and how to get a second chat

Coffee chats tend to happen the week you need something: a new job, a referral, a way into another field. First you find someone who might help, write to a stranger, wait, nudge and agree a time. Then the chat goes flat. You ask what a typical day looks like, they give the answer they've given a dozen times, and you both say "let's stay in touch". Neither of you does.

Better questions fix the flat part. Good coffee chat questions ask about the other person's choices and what they're working on now, not what's already on their LinkedIn. Pick five or six from the set below that fits who you're meeting, follow up on what they say, and end with one of the three questions that set up a second chat. After the questions: how to get the chat without a week of chasing, and how to make sure it isn't the last one.

What is a coffee chat?

A coffee chat is a short, informal conversation with someone whose work interests you, over coffee or on a video call. Nobody is hiring and nobody is being interviewed. It's two people comparing notes, and the questions you bring decide how useful it is.

What questions should you ask in a coffee chat?

The best coffee chat questions depend on who you're meeting. Start with an opener, pick a few from the set that fits, and keep five minutes for one of the questions to end on.

Questions to start any coffee chat

Start with what they're doing now. It's easier to answer than "tell me about yourself", and it gives you something to follow up on.

1. What are you working on at the moment that you're enjoying?
2. What's taking up more of your week than it should?
3. What did your first job in this field teach you that you still use?
4. What's changed most about your work in the last year?

Coffee chat questions for senior leaders

Ask about the decisions behind their career. The job titles are already on LinkedIn.

5. Which early decision in your career mattered more than it looked at the time?
6. What do the best people at my level do that the rest don't?
7. What's a call you made that most people around you disagreed with?
8. What advice do you give a lot that people rarely take?
9. What do you spend time on now that you wish you'd started sooner?
10. If you were in my role today, what would you stop doing?

Coffee chat questions for a peer in your field

A chat with a peer runs both ways. Expect to answer as many questions as you ask.

11. What were you hoping to get out of this chat?
12. Which tool or habit has saved you the most time this year?
13. What are you trying to get better at right now?
14. Whose work in our field do you learn the most from?
15. What worked for you this year that surprised you?
16. What did you try recently that didn't work?

Coffee chat questions for a career change

When you're meeting someone in a field you'd like to move into, describe your current job in one sentence first, so their answers fit you.

17. What do people who move into your field from mine usually get wrong?
18. Which of my skills would carry over, and which would I have to learn from scratch?
19. What does a bad week in your job look like?
20. What's the smallest project I could try to find out whether I'd like this work?
21. Which job titles should I search for, and which ones sound right but aren't?
22. Which companies hire people with a background like mine?

Coffee chat questions for colleagues

An internal coffee chat is how you find out how things actually get done at your company.

23. What does your team need from mine that it isn't getting?
24. What does your team do that the rest of the company doesn't see?
25. Who do people here go to when they're stuck, even when it isn't their job?
26. What's an unwritten rule here that took you a while to learn?
27. What's your team's biggest project for the rest of the year?

Questions to end a coffee chat

These three give you a reason to talk again. Pick one, or ask all three if there's time.

28. What's one thing you're trying to figure out right now? If you come across something useful later, like an article, a tool or a person, that's your reason to write.
29. Is there someone you think I should meet? Meet them, then tell the person who suggested it how it went.
30. Mind if I let you know how it goes? A yes means they're expecting your next message.

What follow-up questions should you ask?

Prepared questions get prepared answers. A follow-up question picks up the last thing they said, and it's the kind of question that makes people enjoy talking to you. A 2017 Harvard study of live conversations found that people who asked more questions, especially follow-up questions, were better liked by the person they were talking to. When the researchers looked at speed dates, people who asked more follow-up questions were more likely to get a second date. The people in the studies didn't expect asking questions to make them more likeable.

Keep a few ready:

• How did you know it was the right call?
• What happened next?
• Why do you think that worked?
• What would you tell someone in that spot today?

How do you get a coffee chat?

The usual way takes four steps:

1. Pick someone. Someone a step or two ahead of you, a peer in your field, or someone in a field you're curious about.
2. Get on their radar. Comment on one or two of their posts before you write to them.
3. Ask for 20 minutes. Say who you are and why you picked them, and offer two times.
4. Nudge once. No reply in a week? Send one short follow-up, then move on.

Every question above comes after someone says yes, and getting the yes is most of the work: finding the right person, writing to a stranger, waiting, nudging, and starting again with the next one. To keep meeting people, you'd do all of that again next week.

Touchbase does that part for you: it introduces you to someone new in your field every week. We find the person, pick a time you're both free and book a 20-minute video call. The other person signed up for these calls too, so nobody needs convincing and nobody is doing anyone a favour. You can each leave a note before the call, which is a good place for your first question from the list above.

How do you get a second coffee chat?

"Let's stay in touch" is where a lot of coffee chats end. A second chat comes from the last five minutes and the day after. End on one of questions 28 to 30. Then send a short message the same day: thank them, and name one thing they said and what you'll do about it. A month or two later, write again with what happened.

If you're unsure whether to send it, the chat probably went better than you think. A 2018 study in Psychological Science found that after a conversation, people consistently underestimated how much the other person liked them and enjoyed their company. The researchers called it the liking gap. They found it between strangers in a lab, at a personal development workshop and among first-year students getting to know their housemates, where it lasted for months.

So send the message. A second chat is where a stranger becomes someone you know a little, and a 2022 study in Science of 20 million LinkedIn users found that people you know a little led to the most job moves.

Touchbase helps here too. You both see each other's name, role, company and LinkedIn before the call, so you know where to find them afterwards. And because you meet someone new every week, one chat that goes quiet doesn't leave you starting again from zero.

Coffee chat etiquette: what to avoid

• Asking what's on their LinkedIn. "So what do you do?" tells them you didn't look.
• Asking for a job or a referral in the first chat. Ask in a later one, once they know you and your work.
• Running over. If you asked for 20 minutes, offer to wrap up at 20, even if it's going well.
• Letting them pay. If you asked them and you're meeting in person, the coffee is on you.

Coffee chats: quick answers

How many questions should you prepare for a coffee chat?

Five or six from the set that fits, plus one of the three to end on. Follow-up questions fill the rest of the time.

How long should a coffee chat be?

Ask for 20 minutes and finish on time. That's enough for five or six questions and their follow-ups, and a short ask is easier to say yes to.

Is a coffee chat the same as an informational interview?

Nearly. An informational interview is mostly you asking about their job. A coffee chat is looser and goes both ways, especially with a peer.

What are some fun coffee chat questions?

Try "What's the best advice you ignored?", "Which tool would you refuse to give up?" or "What would you do with one extra hour a day at work?" They work best halfway through, once you're both relaxed.

What is a virtual coffee chat?

A virtual coffee chat is a coffee chat on a video call instead of in a café. The same questions work. Every Touchbase call is a virtual coffee chat: 20 minutes, in your browser, with someone new in your field.

Is there an app for coffee chats?

Yes. Touchbase matches you with someone new in your field every week and books a 20-minute video call at a time you're both free. It's free. For coffee chats with coworkers, Donut pairs people inside a company's Slack or Microsoft Teams.

Before your next coffee chat

Pick five or six questions for the person you're meeting, keep one of the three to end on, and send the follow-up the same day. Then do it again next week. Touchbase books that chat for you every week with someone new in your field, so by this time next year you'll have met 52 new people. When you next need a job, a hire or a second opinion, you'll already know who to ask. It's free: sign up for Touchbase.