40 Coffee Chat Questions (And When to Use Each One)

A coffee chat lives or dies on its questions. Thirty minutes with an interesting person can produce a genuine relationship or a polite blur, and the difference is almost entirely what you ask. These are questions that reliably produce real answers, grouped by where they belong in the conversation.

Opening — the first five minutes

The job here is to get past the CV version of the person. Skip "tell me about yourself" — you've both already read each other's profiles.

• What are you working on at the moment that you actually find interesting?
• How did you end up doing this? I'm guessing it wasn't a straight line.
• What does a normal Tuesday look like for you?
• What made you say yes to this coffee?
• What's taking up most of your headspace at work right now?

About their work

These get you the operating detail that never appears in a job description — the part you can only learn from someone doing the job.

• What's the part of your job that people outside it completely misunderstand?
• What's the hardest decision you've had to make in this role?
• What do you spend time on that you wish you didn't?
• What would you do differently if you were starting this project again?
• What's a skill that turned out to matter far more than you expected?
• What does someone need to be good at to do well on your team?
• What's changed most about how you work in the last two years?

About their industry

Especially useful if you are new to a market — including new to Australia or New Zealand, where industries are small enough that a single conversation can map most of the landscape.

• Who's doing genuinely interesting work in this space right now?
• What's the thing everyone in the industry believes that you think is wrong?
• How is this market different here compared with the UK or the US?
• What's coming in the next couple of years that people aren't ready for?
• Where does the industry actually hire from — is it advertised roles or referrals?
• Which conferences or communities are worth the time, and which aren't?
• What would you pay attention to if you were entering this field today?

About their career

Ask these once there is some warmth in the conversation. They invite reflection, and reflection is what makes someone remember the chat.

• What's the best career decision you've made, and what made it work?
• What's something you turned down that you still think about?
• Who has had the biggest influence on how you work?
• What advice were you given early on that turned out to be wrong?
• How did you know it was time to leave your last role?
• What would you tell someone at the stage I'm at now?
• What do you want to be doing in five years that you're not doing now?

When they ask about you

A good coffee chat runs both ways. If you only interview them, it becomes an interrogation, and they leave with nothing. Have honest answers ready for these — you will be asked at least one:

• What are you trying to figure out at the moment?
• What kind of problem do you most enjoy working on?
• What would be genuinely useful for you to leave here with?

That last one is worth asking yourself before you arrive. Turning up with a clear answer is what separates a productive half hour from a pleasant one.

Closing — the last five minutes

These questions do the most work and get asked the least. Leave time for them.

• Who else do you think I should be talking to?
• Is there anything I should have asked you that I didn't?
• What's the most useful thing I could do for you?
• Would it be all right if I came back to you once I've made some progress?

"Who else should I talk to?" is the compounding question — one good referral per conversation is what turns a handful of contacts into a network. "What could I do for you?" is the one that makes people remember you, and it is almost never asked by the person who requested the meeting.

Questions to skip

• "What do you do?" — you already know — it wastes the opening.
• "Are you hiring?" — turns a conversation into a transaction. If a role exists, it will come up.
• "Can I pick your brain?" — an unbounded ask disguised as a question.
• Anything you could have found on LinkedIn — it signals you did not prepare.
• Salary, on a first chat — ask about ranges for the market instead of their number.

After the chat

Send a short message within a day or two that refers to one specific thing they said, and do whatever you told them you would do. If they suggested someone to talk to, tell them how it went — closing that loop is the cheapest way to make a second conversation likely.

For the wider picture on building relationships from scratch here, see how to network in Australia, and if you would rather meet people in a room than one-to-one, our networking event tips cover that format.