Questions to Ask on a Coffee Chat
Questions for a short informal chat with someone whose work or career you want to understand, whether you asked for the time or they offered it. Covers how they got there, what the job is actually like, what they would do differently, and how to leave with a next step.
20 questions, each with the reason to ask it · includes a conversation guide
The questions
Open any question to see why it works.
- 1
How did you end up doing this?
Opens with the question most people enjoy answering, and it gets you the real route rather than the tidy version on their profile. Listen for the accidents, because they tell you which doors are actually open to someone in your position.
- 2
What does a normal week look like for you?
Job titles hide enormous variation, and this is how you find out whether the role is meetings, writing, code, or firefighting. It also tells you how much of the week is discretionary, which is the part any job description leaves out.
- 3
Which part of the job takes the most time, and which part do you actually enjoy?
Asking for both halves at once makes an honest answer easy, and the two are rarely the same thing. If the enjoyable part is a small fraction of the week, you have learned something the job posting will not tell you.
- 4
What did you do before this, and what made you move?
The reason for the last move is more useful than the sequence of roles. People leave for money, a manager, boredom, or a shutdown, and whichever they name tells you what they weigh when making decisions.
- 5
What surprised you about this field once you were inside it?
Insiders always have an answer, and it is usually the gap between how the work is described and how it is done. This is the single highest-value question on the list for anyone deciding whether to enter a field.
- 6
What does the first year look like for someone joining at my level?
Shifts the conversation from their story to your situation without asking for anything. The answer gives you a checkable picture of the ramp, the early tasks, and how long it takes before anyone trusts you with real work.
- 7
Which skills actually matter here, and which ones are overrated?
The second half is what makes this worth asking, because it saves you from spending six months on the wrong course or certificate. Answers vary sharply between people, so ask two or three and look for the overlap.
- 8
How did you learn the parts of this job that nobody teaches?
Every field has knowledge that is passed on informally, and this is how you find out whether it comes from a mentor, a first bad manager, or trial and error. If they cannot answer, the field probably has a steep and unhelpful entry curve.
- 9
Who do you work with most closely, and how is the team put together?
Gives you the shape of the organisation, which matters as much as the role. It also surfaces the adjacent job titles you did not know existed, some of which may suit you better than the one you came in asking about.
- 10
How is success measured in your role?
Look for whether they can state it precisely. A crisp answer about specific numbers or outcomes means a well-run function; a vague one usually means performance is judged on impressions, which is worth knowing before you join.
- 11
What is the hardest part of the job that people outside it do not see?
Invites the complaint without making them sound like a complainer, so most people take the opening. This is often where you learn about on-call weeks, politics, travel, or the volume of work that never appears in a case study.
- 12
What is changing in this field that people outside it have not caught up with yet?
Positions you as someone thinking about the work rather than just the job. It also gives you something specific to reference in an application, which is far more effective than repeating language from the company website.
- 13
If you were starting over now, what would you do differently?
Distinct from asking for advice, because it makes them answer from their own experience rather than in general terms. Expect the answer to be about timing, a qualification they did not need, or a network they built too late.
- 14
What do the strongest people you have worked with have in common?
Produces a description of behaviour rather than a list of qualifications, which is what you can actually act on. Note whether the traits are things you can practise or things about background, since only one of those is available to you.
- 15
What makes an approach from someone like me easy to ignore?
People are far more candid about what does not work than about what does. The answer will usually be specific: no context, no clear ask, a generic message, a request for an hour when fifteen minutes would do.
- 16
Where do openings on your team usually come from?
This is the closest you should get to asking about a job, and it is a question about process rather than a request. You are looking for whether hiring runs through referrals, an internal pipeline, or public postings, because it changes what you do next.
- 17
Is there anything in my background that would give you pause?
Hard to ask and worth it, because you are asking a stranger to be briefly critical in private. What they name is almost certainly what a hiring manager is thinking too, and now you can address it before the next conversation.
- 18
What should I be reading, watching, or turning up to?
A small, easy ask that produces a concrete list and gives them something to be helpful about. It also creates a natural reason to follow up later once you have actually done it.
- 19
Who else should I be talking to?
The most valuable question in the whole conversation, and the one people forget. Ask it before you thank them, and if they name someone, ask whether they would be comfortable introducing you rather than assuming either way.
- 20
Would it be useful if I sent you anything after this?
Ends by offering rather than asking, which is what makes the second conversation possible. It also tells you whether they want to stay in contact, because a vague no is a clear answer and worth accepting gracefully.
How to run a coffee chat
Practical guidance for the conversation itself.
Before you turn up
Before you turn up
Ask for twenty minutes and mean it
A short, specific request gets said yes to far more often than a vague one, and it is the most reliable way to get the meeting at all. Then end at twenty minutes yourself, even if they seem happy to continue. Being the person who respected the clock is what earns the second conversation.
Do the reading so you can skip the basics
Anything on their profile, their company site, or their published work should not be asked about. Spend the twenty minutes on the things only this person can tell you: what surprised them, what is hard, what they would do differently.
Decide the one thing you want to leave with
A referral, a reading list, an honest read on your background, or a name to contact next. Twenty minutes is enough for one clear outcome and not enough for four, and people who want everything usually get nothing.
Do not send a CV in advance
It reframes an informal chat as a screening call and makes the other person feel recruited rather than consulted. If they want it, they will ask, and that ask is far more useful than an unrequested attachment.
During the conversation
During the conversation
- Open with why you asked for the time specifically, in one sentence. It sets the direction and stops the meeting drifting into small talk.
- Ask about their experience, not for their prediction about yours. People are precise about what happened to them and vague about what will happen to you.
- Take visible notes. It changes what people are willing to say, because it signals you intend to act on the answers.
- Do not ask for a job. It converts a helpful person into a gatekeeper, and it is the single most common way these conversations get wasted.
- Watch the time out loud once, at around fifteen minutes, and offer to stop. Most people will extend the meeting themselves at that point.
- Leave with a name or a next step. A pleasant chat with no follow-on is a nice twenty minutes and nothing else.
Afterwards
Afterwards
Follow up within a day, briefly
Two or three sentences: thanks, the one thing you took from it, and what you are doing as a result. Specificity is what makes it memorable, and a note that could have been sent to anyone is worse than no note.
Actually do the thing they suggested
If they named a book, a group, or a person, follow it up and then say so. This is the entire mechanism by which a stranger becomes someone who will vouch for you later.
Come back once, with something
A month or two later, send an update or something genuinely useful to them, not another request. One well-timed follow-up creates a real contact; three unprompted asks end one.
Do not chase an introduction that was not offered
If you asked who else you should talk to and no introduction followed, take the name and approach the person yourself, mentioning the conversation. Pressing for a warm handoff that was declined costs you the original relationship.