Questions to Ask in a Coffee Chat
Questions for a half-hour networking coffee with someone whose work or company you want to understand. They cover what their days actually look like, how decisions get made, how they got there and how people get hired, with a group for a coffee meeting with a recruiter, when no role is on the table yet, and a last one on asking for a next step without overreaching.
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The questions
Each question, and why to ask it
Their work
What are you working on this month?
Why ask it
Present tense keeps the answer concrete. Asking what someone does invites a job description, while asking about this month gets you the project, the deadline, and the frustration, which is where every useful follow-up comes from.
How did you end up in this role? I would like the actual path, not the resume version.
Why ask it
The permission to skip the polished story usually gets you the accidents: a manager who moved teams, a project nobody wanted, a year that did not work out. Those details are what tell you whether your own odd path is a problem here.
What does a normal day look like for you?
Why ask it
People describe their job by its interesting ten percent. Walking through a day surfaces the other ninety: the standing meetings, the approvals, the inbox. That is what you would actually be signing up for.
What surprised you most about this company after you joined?
Why ask it
This is the safest way to ask what the company is really like, because it invites a comparison rather than a complaint. Answers about how long decisions take, or how little structure there is, are the ones worth writing down.
Which of your skills do you use every day, and which have you barely touched since you started?
Why ask it
The second half is the valuable half. Hearing that the modelling or the design work they were hired for has been replaced by coordination tells you what the role becomes over time, which no job posting will.
What part of the job do you like least?
Why ask it
Asked plainly and without a wince, most people answer. If they deflect entirely in a private conversation with no stakes, that reticence is itself worth noting about the culture.
What is something people outside this field get wrong about it?
Why ask it
The answer often corrects an assumption you were about to build a plan on, and it lets them be the expert, which tends to open up the rest of the conversation.
How does work actually get decided on your team? Who has to say yes?
Why ask it
You are asking for the org chart that matters. Whether a project needs one director or four sign-offs predicts how fast anything moves, and it tells you who to talk to next if you want in.
What did your first ninety days here look like, and what would have helped?
Why ask it
This is the best proxy for onboarding quality available from the outside. Someone who describes finding their own way for a quarter is describing a company that hires people and leaves them to it.
What are you reading or following to keep up?
Why ask it
You get a short list you can actually use, and the shape of it is informative: industry newsletters, a specific analyst, or a group chat all suggest different ways this field shares information.
What is the hardest part of your week that has nothing to do with the work itself?
Why ask it
This is where the commute, the time zones, the on-call rotation, or the political maneuvering comes out. These are the things people leave jobs over, and they never appear in a recruiting conversation.
How is success measured in your role?
Why ask it
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.
What is changing in this field that people outside it have not caught up with yet?
Why ask it
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.
What do the strongest people you have worked with have in common?
Why ask it
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.
Their story
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.
If you were starting over in this field now, what would you do differently?
Why ask it
The word now is what makes this useful. A route that worked five years ago, a particular certificate, a rotational program, an agency job, may be closed or no longer worth the time, and the people already inside are the ones who know which.
Was there an opportunity you turned down that you still think about?
Why ask it
Regret makes people specific. Instead of the advice they give everyone, you get the reasoning behind one real trade-off they made, usually pay against learning or stability against interest.
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.
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'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 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 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.
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.
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.
How did you learn the parts of this job that nobody teaches?
Why ask it
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.
Getting in
Has anyone joined your team from a background like mine, and how did they make the case?
Why ask it
This turns a vague question about whether you could get in into an answer about evidence. If the answer is no one, that is worth knowing early, and if it is yes, you now have both a precedent and a name.
What is the team hiring for, and what makes someone stand out in that process?
Why ask it
Asked this way it stays a question about the team rather than a request for a referral. People who screen resumes will often tell you the exact thing they look for first, which is rarely what the posting emphasises.
What does the first year look like for someone joining at my level?
Why ask it
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.
Where do openings on your team usually come from?
Why ask it
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.
What makes an approach from someone like me easy to ignore?
Why ask it
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.
Is there anything in my background that would give you pause?
Why ask it
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.
With a recruiter
Is this coffee part of how the company assesses people, or is it off the record?
Why ask it
Some employers have recruiters log a line after every coffee chat and some write nothing down, so the only way to know is to ask how it works there. Asked lightly at the start, it reads as someone who understands the process, and the answer tells you how candid you can afford to be.
Which teams do you recruit for, and which of them are adding people this year?
Why ask it
An employee can describe one team. A recruiter sees headcount across several, so this is the question only they can answer, and it may point you at a group you had not thought to look at.
What does the hiring calendar look like from your side: when do roles open, and when is it too late?
Why ask it
Timelines differ by company and by intake, and the public deadline is not always the date that matters. Hearing when the shortlist is really drawn up tells you whether to apply this month or prepare for the next round.
When you screen applications for this company, what gets someone moved to the yes pile?
Why ask it
The recruiter is usually the first reader, and the first read is quick. Whatever they name, a particular kind of project or a clear reason for wanting this company, is what the top third of your resume should show.
With my resume as it stands, which role here would you put me forward for?
Why ask it
It turns a general chat into a specific reading of you without asking for a job. If the role they name is more junior or on a different team than you expected, that is how your resume reads to the person who filters them, and it costs nothing to hear it over coffee.
Does a referral from someone on the team change how an application is handled?
Why ask it
Referral rules are different at every employer: at some a referred resume is read by a person first, at others it only adds a flag. Knowing which decides whether your next coffee should be with someone on the team before you apply.
Should I apply now for the closest role, or wait for one that fits better?
Why ask it
Candidates agonise over this and recruiters answer it every week. Some companies hold an earlier rejection against a later application for a set period and some do not, so ask what their practice is before you spend the attempt.
What reasons do people give when they turn down an offer from you?
Why ask it
Recruiters hear a side of hiring that no employee does: the pay gap, the location, the team someone met and did not warm to. One who answers this plainly is one whose other answers you can lean on.
What can you tell me about levels and pay bands now, and what should wait until there is a role to talk about?
Why ask it
Pay is part of a recruiter's job in a way it is not for anyone else you will meet for coffee, so the subject is fair, but this early it helps to let them draw the line. How much they can share depends on the employer and, in some places, on local rules about posting ranges.
Wrapping up
What would you want to know if you were sitting where I am?
Why ask it
It hands them the agenda, and experienced people often use it to raise the thing they think you have not considered. Whatever they volunteer here is usually the most useful sentence of the meeting.
Who else should I be talking to?
Why ask it
Ask before the conversation winds down, while there is still time to hear why each name matters. A specific answer with a reason attached is a real introduction; a general suggestion to network more means the conversation did not land.
Is there anything I could send you or help with?
Why ask it
Small and genuine beats grand and vague. Sometimes there is a real answer: an introduction of your own, a document, a candidate for a role they mentioned. Even when there is not, offering gives you a reason to write again.
How do you prefer to keep in touch with people you meet this way?
Why ask it
Some people want an occasional email, some never open one, some would rather you comment on their posts. Asking removes the guesswork that leaves most coffee chats ending with no second contact.
Would it be alright if I followed up in a few months to tell you what came of this?
Why ask it
It sets up a reason to write again that is not a favour, and people who said yes to coffee almost always say yes to this. Then actually do it, since the follow-up is where these conversations turn into something.
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.
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.
Running a good coffee chat
Practical guidance for the conversation itself
Setting it up
Ask for a specific, small amount of time
Twenty or twenty-five minutes gets accepted more often than an hour, and it forces you to prepare. Say what you want to talk about in the invitation so they can decline if they are the wrong person.
Come with four questions, not twenty
Long lists turn the meeting into an interrogation. Pick a handful, and plan to spend most of the time following up on whatever they answer first at length.
If the coffee meeting is with a recruiter
There is usually no single role on the table, so questions about one position land badly. Ask about the company as a whole: which teams hire, when, and what gets an application through. Unless they tell you otherwise, assume a line about the conversation may be written down.
Do the reading they can tell you did
Their recent work, their company's last announcement, the team's job postings. Referencing one specific thing changes the tone of the whole conversation, and it saves you from asking what the company does.
During the conversation
- Say what you are hoping to get out of it in the first two minutes, then stop talking.
- Watch the clock and offer to end on time. Offering usually earns you extra minutes.
- Take notes on paper or say you are taking notes on a laptop, so it does not look like distraction.
- Follow the thread they get animated about, even if it is not on your list.
- Keep your own story to a couple of minutes unless they ask for more.
What makes these go badly
Asking for a job in the first meeting
It changes the register from conversation to transaction, and puts them in the position of declining. Ask about how hiring works and what stands out instead, then follow up with a specific request later.
Asking questions your host cannot answer
A senior leader knows the strategy, not what a junior analyst's Tuesday looks like, and a recruiter knows the hiring calendar, not what the team argues about. Match the question to the seat.
Sending your resume unprompted
Attaching it to the thank-you note reframes the coffee as an application. Wait until they ask, or until you have a specific role to reference.
No follow-up at all
Most of these conversations produce nothing because nobody writes again. A short note within a day, and one more when you have news, is the whole difference.
Afterwards
- Send a short thank-you within a day that mentions one specific thing you are going to do because of the conversation.
- Act on any introduction they offered within a week, while the referral is still warm, and tell them what happened.
- Note in your own file what they cared about, what they warned you about, and anything personal they mentioned.
- Write again in a few months with a result, not a request.