Coffee Chat Questions to Ask
Questions for coffee chats and informal one on ones, whether it is a new colleague, a contact from a networking event, or a friend you have not seen in a while. The early ones are light enough to open with, the later ones are the sort you only get to once the conversation has warmed up, and the last two turn a single chat into a next step.
The questions
Open any question for the note
What have you been up to lately that you are actually enjoying?
Why ask it
The word "enjoying" quietly rules out the recited status update. People answer with something real, often a side project or a small change at home, and that is a much better starting point than a job title.
What has your attention outside of work right now?
Why ask it
Gives permission to talk about something they are invested in rather than something they are paid for. If the honest answer is that there is nothing, that is worth hearing too, because it usually means the job has taken over.
How did you end up doing what you do now, and what nearly happened instead?
Why ask it
Careers are rarely straight lines, and the road not taken is usually the more interesting half. The near-miss also tells you what they were choosing between, which is the part a CV can never show.
What is the best thing you have read, watched or listened to in the last month?
Why ask it
Low stakes and easy to answer, but the choice carries information: what they seek out when nobody is assigning it. A blank here is common and not a bad sign, it often just means small children or a hard quarter.
What does a good weekend look like for you these days?
Why ask it
The phrase "these days" acknowledges that this changes, which makes it easier to answer honestly than a question about hobbies. Answers tend to reveal how much slack someone currently has in their life.
What is something you learned recently that surprised you?
Why ask it
Surprise is the useful word. It filters out facts they merely collected and gets to something that shifted their view. People often need a few seconds of silence here, so resist filling it.
What part of your work would you keep if you could hand off the rest?
Why ask it
A sharper version of asking what they like about their job, because it forces a choice. What someone would keep is normally the work they are best at, and it tends to predict what they will do next.
What do people usually get wrong about what you do?
Why ask it
Almost everyone has a stock frustration here, and it is often the first genuinely animated answer of the conversation. It also saves you from making the same wrong assumption for the next half hour.
Who taught you the most about how to do this?
Why ask it
Naming a person, rather than a course or a book, produces stories with detail in them. It also shows how they learn, whether by close apprenticeship or largely alone, which is worth knowing if you might work together.
What advice did you get early on that turned out to be wrong for you?
Why ask it
More useful than asking for their best advice, which produces something polished and repeatable. Rejected advice tells you what they had to unlearn, and it gives you permission to disagree with received wisdom too.
What are you trying to get better at right now?
Why ask it
Present tense keeps this concrete. A specific answer, such as running a meeting without over-explaining, opens a real exchange. A general answer about growth usually means they have not thought about it lately, which is fine to note and move on from.
What part of your week would you protect if everything else on your calendar got cut?
Why ask it
Reveals what someone genuinely values, which is more reliable than asking about priorities directly. People describe their priorities aspirationally, but they defend their calendar honestly.
What is the most interesting thing on your desk at the moment?
Why ask it
Invites them to talk shop at whatever depth they choose, without you needing to know the field. Listen for whether they light up about the problem itself or about the politics around it, because those are different people to know.
What have you changed your mind about in the last year?
Why ask it
Signals that you are interested in how they think rather than what they currently believe. Anyone who can answer this quickly and specifically is usually worth staying in touch with.
What is something you keep meaning to start and have not?
Why ask it
Easier to answer than a question about goals, because it comes with a built-in excuse. The reason they give, whether time, money, nerve or permission, tends to be the more revealing half of the answer.
What was harder about the last year than you expected?
Why ask it
Ask this only once the conversation has some warmth, and offer something of your own first. Framed as a mismatch of expectations rather than a hardship, it lets someone be honest without having to make it a confession.
If you were starting out again now, what would you do differently?
Why ask it
Draws out what they think has changed about their field, not just their own regrets. Pay attention if they say they would not change anything, then list three things they would; the list is the real answer.
What would you like to be doing in two or three years, if it goes the way you want?
Why ask it
The conditional makes it safe to say something ambitious or something quiet. Vague answers here are common and not evasive, most people have a direction rather than a plan, and the direction is what you want.
Is there anything I can help with, or anyone I should introduce you to?
Why ask it
Turns a pleasant hour into a two-way exchange, and the honest version of asking for a favour is offering one first. Keep it small and specific enough that yes is easy, then actually do it within the week.
Who else should I be talking to, and what should I ask them?
Why ask it
The second half is what makes this work: it gets you a warm introduction and an opening line at the same time. If they cannot think of anyone, take it as a sign the conversation stayed shallower than you hoped.
Running a coffee chat that goes somewhere
Practical guidance for the conversation itself
Set it up well
- Ask for a specific length and keep to it. Thirty minutes gets accepted far more often than an open-ended coffee, and finishing on time is the main reason someone agrees to a second one.
- Name the reason in your invitation, even if it is thin: a shared project, a mutual contact, something they wrote. Unexplained invitations get read as a sales approach.
- Pick somewhere quiet enough to hear each other and pay for the coffee if you asked for the meeting. Both matter more than they should.
- Have three questions ready and expect to use one. The point of preparing is not to work through a list, it is to avoid the dead pause at minute four.
During the conversation
Go second, not first
When you want a real answer to something slightly personal, offer your own version first and keep it short. Asking what was hard about someone's year lands very differently when you have already named something about yours.
Follow the energy, abandon the list
If they get animated about one thing, stay there. Three questions deep on a single subject is a better conversation than ten questions on ten subjects, and it is the difference between an interview and a chat.
Let silences run
The good answers usually arrive after a pause, because the first response is the rehearsed one. Count to three before you rescue the moment. Most people fill their own silence with something more honest.
Aim for roughly two thirds them
Not all questions and no substance of your own, which feels like an interrogation, and not an even split, which usually drifts into you talking. Answer briefly when asked, then return the question.
What makes these go flat
Opening with what you want
If you need something, a referral or an introduction or advice on a decision, save it for the last ten minutes. Leading with the ask means everything before it reads as a preamble, and they will remember the ask rather than the conversation.
Stacked questions
Two questions in one sentence gets you an answer to the easier half. Ask one, stop talking, then ask the follow-up you actually cared about.
Cross-examining a guarded person
Some people are private, tired, or in a bad month. If short answers keep coming, drop to lighter ground, talk about something concrete you are both looking at, and let the depth come another time or not at all.
Letting it end without a thread
Send a short note the next day referring to one specific thing they said, and do the small thing you offered. A chat with no follow-through is a pleasant hour that neither of you will build on.
Adjusting for who you are meeting
A new colleague
Ask how they like to be given work and what they wish more people asked them about. Skip career-path questions in the first meeting; you will get better answers once you have worked on something together.
A contact from a networking event
Assume they do not remember the details of your conversation, and remind them in one line without making it awkward. Spend the middle of the meeting on their work and the end on who else you should each know.
A friend you have not seen in a while
Resist the urge to do a chronological catch-up on jobs and houses. One question about what has changed for them internally, asked after the news is out of the way, is what makes it feel like seeing each other again.
Someone more senior who agreed to twenty minutes
Pick two questions in advance, ask them early, and end on time even if they seem willing to keep going. Being the person who respected the clock is what gets you the second conversation.