Questions to Ask in a Coffee Chat
Questions for a half-hour coffee with someone whose work or company you want to understand, covering what their days actually look like, how decisions get made, how they got there, and how to ask for a next step without overreaching.
The questions
Open any question for the note
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 Hearing that the modelling or the design work they were hired for has been replaced by coordination tells you what the role becomes over time, which no job posting will.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.
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.
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 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.
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.
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.
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. 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.