Questions to Ask at a Coffee Chat
Twenty questions for a half-hour coffee with someone you are still getting to know, whether it is a new acquaintance or an introduction made through work, plus how to end it well.
The questions
Open any question for the note
How did you end up doing what you do now?
Why ask it
Almost everyone has a version of this ready, so it costs them nothing and gives you a lot: the accidents, the person who opened a door, the plan that did not happen. Listen for what they skip over, because that is usually where the interesting part is.
What were you doing five years ago, and would you have predicted this?
Why ask it
The gap between then and now is where the real story lives, and most people find the second half of the question funny. It also tells you how much of their path they attribute to intention rather than luck.
What does a normal week actually look like for you?
Why ask it
Job titles hide the work. Ask for the shape of the week and you get meetings, travel, the hours nobody sees, and whether they like it, which is far more useful than a description of the role.
What part of it would surprise someone looking in from outside?
Why ask it
Invites them to correct a public misconception, which is a question people enjoy answering. The answers tend to be about how much of the work is administrative, or how little control anyone actually has.
What's taking up most of your attention at the moment?
Why ask it
Present tense keeps it concrete and lets them choose between work and life. It is also the question most likely to surface something you can help with later, which matters if you want a second conversation.
What have you changed your mind about recently?
Why ask it
Reliably produces something unrehearsed, because nobody prepares this answer. Someone who cannot think of anything is telling you something too, and the silence is usually worth waiting out rather than filling.
What do you spend your time on that has nothing to do with work?
Why ask it
Necessary if the conversation has been all professional, and it is often where the person becomes memorable: a boat, a choir, a plot of allotment. It also keeps a networking coffee from feeling like an interview.
What have you been reading or listening to that you'd recommend?
Why ask it
A low-cost question that gives you both something to follow up on, and following up on it is the easiest way to earn a second meeting. Vague answers usually mean they are tired, not uninterested.
Who has had the biggest influence on how you work?
Why ask it
Answers point at a former manager, a colleague, or occasionally a bad example they decided not to repeat. The last kind is the most revealing, because it tells you what they are trying not to be.
What would you do differently if you were starting out again?
Why ask it
More candid than asking for advice, because it lets them talk about their own decisions rather than yours. Expect regrets about moving too slowly, staying too long, or optimizing for the wrong signal.
What's a decision you made that looked risky at the time?
Why ask it
Gets a specific story rather than a philosophy, and the details, what they gave up and who advised against it, are the part you will remember. It also tends to be the moment the conversation stops being small talk.
What would you like to be doing more of a year from now?
Why ask it
Forward-looking and personal without being intrusive. It often reveals a plan they have not announced publicly, which is worth remembering and not repeating.
How do you know the person who introduced us?
Why ask it
Cheap to ask and it tells you what the introduction was actually based on, which is often not what you assumed. It also gives you a shared reference point to come back to when the conversation runs dry.
What's a question you wish people asked you more often?
Why ask it
Hands them the wheel, and most people have a topic they never get asked about despite knowing a great deal. The answer usually saves you three questions you would otherwise have guessed at.
Where do you go to find people who are good at what you do?
Why ask it
Points at the conferences, group chats and mailing lists that are not obvious from outside, which is worth more than a book recommendation. It also shows whether they are still learning from peers or working in isolation.
How do you decide what to say no to?
Why ask it
Priorities show up more honestly in refusals than in stated goals, and everyone has a rule of thumb here even if they have never said it aloud. Someone who says they say yes to everything is describing their calendar accurately.
Is there anything you're stuck on that I could help with?
Why ask it
Coffee chats where only one person asks for things rarely happen twice. Offer something concrete, an introduction, a document, a couple of hours, and be prepared for the answer to cost you less than you expect.
Is there anything you were hoping to get out of this that we haven't covered?
Why ask it
Assumes they came with a reason of their own, which is usually true and rarely stated. Asking with five minutes left gives them room to raise it without having to interrupt you.
Who else do you think I should talk to?
Why ask it
The most valuable question in the conversation, and the one people forget to ask. If a name comes up, ask whether they would be comfortable making the introduction rather than leaving you to send a cold message.
What's the best way to stay in touch?
Why ask it
Ends the meeting with something actionable and lets them set the terms, which some people want to keep loose. Their answer tells you how much of a connection this actually was, and following it exactly is what keeps it alive.
Running a good half hour
Practical guidance for the conversation itself
Setting it up
Ask for a specific, short slot
Twenty-five or thirty minutes at a named time gets accepted far more often than an open invitation to coffee sometime. Say plainly why you want to talk to this person in particular.
Arrive with three questions, not twenty
A short meeting only has room for a few, and a list you are working through changes the feel of the conversation. Choose three and let the rest go where it goes.
Do the basic reading first
Anything you could have found out in five minutes online is a waste of the time you asked for. Reading it also lets you ask a better version of the obvious question.
Buy the coffee, and end on time
You asked for the meeting, so cover it, and start wrapping up at the twenty-five minute mark yourself. Ending early and cleanly is what makes a second meeting easy to ask for.
During the conversation
- Follow the answer, not the list. One question with three follow-ups beats five questions asked in order.
- Let pauses sit. The second half of an answer, after the silence, is usually the honest half.
- Match what you take with what you give: an observation, a contact, something you know that they do not.
- Take notes afterwards rather than during, unless you ask first. Writing while someone talks changes how much they say.
- Do not ask for a job in a first conversation. Ask about the work, the team and who else to talk to, and let the rest follow.
The part most people skip
Send one short note within two days
Reference something specific from the conversation and include whatever you offered. A note that mentions nothing concrete reads as a formality and is treated as one.
Actually follow up on the introduction
If they offered to connect you with someone, make it easy: send a two-line message they can forward. Offers that go unused rarely get repeated.
Report back later
Telling someone months afterwards what you did with their advice is uncommon enough to be memorable, and it is the main thing that turns one coffee into an ongoing relationship.