The best coffee chat questions are few and specific. Bring one main question that only this person can answer, 3 or 4 smaller ones that support it, and one to close. A 30-minute coffee holds about 5 questions, so a list of 50 mostly tells you what to cut. Here is how to choose.
How many coffee chat questions fit in one coffee
Fewer than the lists suggest. MIT’s career office describes these conversations as short, 20 to 30 minutes, and the same page offers 33 questions to choose from. RBC’s guide to coffee chats says to stop at 30 minutes and to allow roughly 5 to 7 minutes a question.
Do the arithmetic and you get 4 to 6 questions. Take off the minutes spent ordering, sitting down and saying goodbye, and 5 is a generous count.
That changes the job. You are choosing 5 questions, and the order matters, because the last 2 may never get asked. Put the one you care about most near the front.
Start with the question only this person can answer
A useful test for any question on your list is whether a search could answer it. If it could, leave it out. The person across the table gave up part of their afternoon, and the fair use of that time is the thing that lives only in their head.
That usually means a question built from 2 parts. One part is something specific they have done. The other is something specific you are facing.
- A photographer who has shot the same 4 blocks for 20 years. “What do you notice on that street now that you walked past for the first 10 years?”
- A founder who closed her first company and started a second. “I am deciding whether to keep going with mine. What did you know in the last 6 months that you wish you had acted on sooner?”
- A ceramicist who left an office job. “How did you know the work was good enough to charge for?”
- Someone who has lived in the neighborhood for 30 years. “If I only had Saturday mornings to get to know this place, where would you send me?”
A question that fits one person tells them you came to meet them, and it gives them something they can answer well.
Write that question down before you ask for the coffee. It also makes the invitation easier to write and easier to accept. Sean Blanda, a content executive whose advice was collected by PPAI Media, puts it plainly. Skip “can I pick your brain,” and arrive with one clear, specific ask.
Coffee chat questions that open a conversation
Around your main question, bring a handful of others. These are starting points. Rewrite each one so it could only be asked of the person you are meeting.
To begin
- What are you spending most of your attention on this month?
- I read or saw the thing you made last year. What happened after it came out?
- What made you say yes to this coffee?
About how they see their work
- What do people usually get wrong about what you do?
- What part of the work still surprises you?
- What do you do differently now from when you started?
- What do you pay attention to that a newcomer would miss?
About a decision you are facing
- Here is the choice in front of me. What would you want to know before making it?
- What would you try first if you were in my position with a free month?
- What is the cheap way to find out whether I am wrong about this?
About taste and place
- Whose work do you keep going back to?
- Where in the city do you go to think?
- What is worth my time here that almost nobody mentions?
To close
- What should I have asked you that I did not?
- Is there someone else you think I should sit down with?
- May I tell you how this turns out?
Pick 1 or 2 from the groups that fit, add your main question, and stop. If you bring 12, you will spend the coffee looking at your notes.
Questions to leave at home
Some questions cost the other person more than they give you.
- Anything their public work already answers. Where they work, what they made, how long they have done it. Read that first and use the minutes for what comes after it.
- The broad life question. “Tell me about your journey” hands them a 20 minute monologue and you a summary you could have found yourself.
- The interview question. Asking someone to name their biggest mistake or greatest weakness can feel like a hiring panel. If you want to hear about a hard stretch, ask about a specific one and let them decide how much to say.
- The favor in disguise. If you want an introduction, a job or feedback on a deck, say so when you ask for the coffee, so they can agree to that or decline it. Do not save it for minute 28.
- Money, unless they open the door. What someone earns or charges is theirs to raise.
What your questions feel like from the other chair
Most advice on coffee chat questions is written for the person asking. It helps to sit in the other chair for a minute.
Someone who is often asked for their time hears the same request in many forms, and the hard part for them is rarely the half hour. The request is vague. They need to know what you want, how long it will take and how they will know it went well. A vague request asks them to do the planning too.
Good questions fix that before you meet. One clear subject tells them what to think about on the walk over. A stated length tells them when they can leave without being rude. A public coffee shop at a quiet hour keeps it easy for both of you. Asking this way is a courtesy.
The same holds once you are at the table. Say your main question early, keep an eye on the time yourself, and end when you said you would, even if it is going well. They can always offer to stay.
When the conversation stalls
It will, briefly, and that is fine. These 3 moves work better than reaching for the next question on the list.
- Follow up on what they just said. “What made you choose that?” and “What was hard about that part?” go further than a fresh topic. The best coffee chats are 2 or 3 questions and a lot of follow-up.
- Offer something of your own. Say what you are working on and where you are stuck. A conversation where only one person answers starts to feel like an interview.
- Let the quiet sit. A pause after a real question usually means they are thinking. Give it a few seconds before you fill it.
After the coffee
Send a short note the same day. Name one thing they said that changed how you see your question, and say what you plan to do about it. If they suggested someone to meet or something to read, follow through, then tell them how it went.
Questions people ask
How many questions should I bring to a coffee chat?
Bring about 5. That is one main question, 3 or 4 smaller ones and one to close. Rank them, because you may only get through 3. A longer list is useful while you prepare and unhelpful at the table.
How long should a coffee chat last?
Plan for 20 to 30 minutes and say the length when you ask. Blanda’s advice is “30 minutes or less,” and to keep to whatever you booked. If it is going well, let the other person be the one to extend it.
What should you not ask in a coffee chat?
Leave out anything a search would answer, anything that sounds like a job interview, questions about their income, and requests you did not mention when you asked for the meeting.
What do I do if I run out of questions?
Ask a follow-up about the last thing they said, or share where you are stuck and ask what they would do. Running out of prepared questions often means the conversation has become a real one.
Who pays for the coffee?
You asked, so offer. If they insist on paying for their own, let them and move on. Blanda’s rule, as PPAI Media reports it, is to spend no more than a few seconds on it.
What is the best question to end a coffee chat with?
“What should I have asked you that I did not?” It gives them room for the thing they hoped you would bring up, and it often produces the most useful answer of the half hour.
One person, one question, one table
A coffee with someone you admire works when it has a shape. That means a person you chose on purpose, a question worth their time and a clear end.
SEYA curates purposeful face-to-face conversations with remarkable people in the city’s most vibrant coffee shops. Each Session is 2 people, one topic and one table, for roughly 20 to 60 minutes. If there is someone in your city you would like to sit across from, start at seya.world.