12 min read
Good coffee chat questions help you understand someone’s actual work, the choices behind their career and what you could try next. Start with “What does a typical week in your role look like?” Then ask questions that fit your situation: getting your first experience, changing fields or preparing for a job search. Bring five or six questions, follow the answers and finish within the time you agreed on.
If you’ve ever sat down for coffee and suddenly forgotten everything you wanted to ask, it helps to have a few questions ready. Keep them nearby, but give yourself room to wander. An interesting story is worth following even if it takes you off your list.
Five coffee chat questions you can use today
If your chat is coming up soon, start here:
“What does a typical week in your role look like?”
“How did you find your way into this work?”
“What surprised you most when you started?”
“What would help someone at my stage get a feel for this work?”
“What’s one thing you’d suggest I try next?”
Pick two or three and follow up on whatever catches your attention. The aim is to hear about their experience, not finish a checklist.
What is a coffee chat?
A career coffee chat is an informal conversation to learn about someone’s work and experience. It can happen at a café, over lunch or on a video call. When the purpose is career exploration, it overlaps with an informational interview. Berkeley Career Engagement describes informational interviews as conversations typically lasting 20–30 minutes, intended to explore a field rather than ask for a job.
Pick the questions you’re actually curious about. You can ask them in your own words—there’s no need to sound like you’re conducting an interview.
Before the chat: choose one thing you want to learn
Read the person’s public profile and their organization’s website. Skip questions you can answer there. Write down one goal, such as “Understand whether customer success suits me” or “Find out what a junior analyst needs to demonstrate.”
Prepare a brief introduction:
“Thanks for meeting me. I’m studying economics and exploring analyst roles. I’d love to understand what the work is like and how to get some relevant experience. Does 25 minutes still work for you?”
For a career change, replace the background and goal with your own. You can be honest about searching for work without making the other person responsible for finding it.
Sometimes you know what you want to learn before you know whom to ask. That’s a useful starting point for LunchME: tell your AI agent the kind of person you’d like to meet, find someone relevant and send a coffee or lunch invitation. You might start with “I’d like to meet someone who moved from hospitality into customer success.” That same goal gives you something to talk about when you sit down together.
If you’re starting from scratch in Toronto, our guide to building a professional network in Toronto can help you think about whom to invite.
Opening questions that work across career stages
Start with something easy to answer from experience:
“What has been taking up most of your time at work lately?”
“How did you find your way into the work you do now?”
“What does a typical week look like, including the less visible parts?”
“What do people outside your role tend to misunderstand about it?”
“What’s a problem you enjoy working on, and what makes it interesting?”
Choose one opener. If they mention a project, ask “What was your part in that?” or “What made it difficult?” Keep questions about projects broad enough that they can answer without sharing confidential information.
Coffee chat questions for students
Focus on the work itself and the smallest useful way to get experience. You do not need a settled career plan to have a worthwhile conversation.
“When you started, which parts of the job were hardest to learn?”
“What can a student do to understand this work before applying for an internship?”
“Which skills do you use regularly that your classes didn’t prepare you for?”
“What would make a class project useful evidence of ability for a junior role?”
“How do interns or new graduates usually contribute on a team like yours?”
“What feedback helped you improve early in your career?”
“If I could try one small project this semester, what would help me test whether I enjoy this field?”
For example, after question four, you could ask: “Would you focus more on explaining my process or polishing the final result?” That gives the other person a concrete choice to discuss.
You don’t have to leave with your career figured out. A project to try, a skill to practise or a role you’d like to hear more about is plenty. Ask a few people about their experience; their answers may give you different ideas about what to explore next.
Coffee chat questions for career changers
Ask what transfers, what is missing and how to test the move before committing. A familiar job title can involve very different work across organizations.
“Which parts of your previous experience were useful when you entered this field?”
“What did you have to learn from scratch?”
“How does this role differ between a small team and a larger organization?”
“What evidence would help someone with my background demonstrate relevant skills?”
“What trade-offs surprised you about the move, such as schedule, responsibility or pace?”
“What is a small, realistic way to try this kind of work before retraining or leaving a job?”
“Which adjacent roles would be worth exploring if this particular move isn’t a fit?”
A little background makes these questions easier to answer. Try: “I’ve spent four years resolving customer issues in hospitality, and I’m exploring customer success.” Then ask which parts of that experience would carry over and what you would still need to learn.
If they recommend a course or credential, follow up with: “What would that help me do, and is there another way to demonstrate the same skill?” Treat a recommendation as something to investigate, rather than a requirement for an entire industry.
Coffee chat questions for job seekers
Use the conversation to understand responsibilities and expectations so you can make better application decisions. Keep applying through the appropriate channels; a chat does not guarantee an interview or referral.
“What would someone in a role like this need to accomplish in their first three months?”
“Which responsibilities tend to take up more time than the job description suggests?”
“How does your team judge whether a project has gone well?”
“What kinds of examples help a candidate show they can do this work?”
“Which teams would this person work with most, and what makes that collaboration effective?”
“What should I look for in a posting to tell whether a role fits my experience?”
“Where can I find public information about the application process for roles like this?”
If you discuss a live opening, be specific about what you have already read. For example: “The posting mentions both reporting and stakeholder presentations. In your experience, how do those responsibilities fit together?” They may not know the role or be involved in hiring; give them room to say so.
For the broader evidence and limits of referrals, read Does Networking Actually Help You Get a Job?.
How to turn an answer into a conversation
Listen for a decision, difficulty or example you want to understand. Then ask one follow-up:
To make an answer concrete: “Could you walk me through a non-confidential example?”
To understand judgment: “How did you decide what to prioritize?”
To clarify a term: “What does that mean in your day-to-day work?”
To connect it to your situation: “Would that advice change for someone entering at a junior level?”
Briefly share something relevant from your own experience when it helps. Then leave space for their response. If an answer already covers your next question, skip it. The useful part is what you learn together, not how many questions you finish.
What a natural follow-up sounds like
Here’s an example of how one question can lead to a useful exchange:
You: “What surprised you most when you started in customer success?”
Them: “How much time I spent working with other teams. I thought most of the job would be customer calls.”
You: “Who did you end up working with most?”
Them: “Product and support, especially when a customer needed something we couldn’t solve right away.”
You: “I coordinate with the kitchen and front desk in my current role. What feels different when you’re doing that across a software company?”
That’s a question, a follow-up and a little shared context. You can stay with that thread rather than rushing to the next item on your list.
A simple 20–30 minute coffee chat plan
If having a plan helps you relax, use this loose 25-minute outline. You don’t need to watch the clock every minute—just leave enough time to wrap up without rushing.
Time | What to do | Example |
|---|---|---|
0–3 minutes | Thank them, confirm the time and introduce your goal. | “I’d like to understand how people get started in this work.” |
3–7 minutes | Ask about their path or current work. | “What does a typical week look like?” |
7–18 minutes | Explore two or three relevant questions with follow-ups. | “What did you have to learn from scratch?” |
18–22 minutes | Summarize what you learned and identify one next step. | “It sounds like a small project would help me test this. What should I focus on?” |
22–25 minutes | Thank them and ask whether staying in touch is welcome. | “Would it be okay if I sent a brief update after trying that?” |
For a 20-minute meeting, shorten the middle section and start closing around minute 17. For a 30-minute meeting, use the extra time for a deeper example. Always keep the agreed end time unless they explicitly offer to continue. Berkeley’s guidance also recommends respecting the timeframe and asking permission to reconnect.
Questions to avoid asking directly—and better alternatives
Some topics are useful but need context and permission. Others ask for information the person should not share.
Avoid leading with | Try instead |
|---|---|
“Can you get me a job?” | “What experience would help me prepare for a role like this?” |
“Will you refer me?” before they know your work | “What would you need to understand about someone’s work before feeling comfortable recommending them?” |
“How much do you personally earn?” | “Where would you look for reliable salary ranges for this role and level?” |
“What exact questions are on your hiring test?” | “Which skills should I be ready to demonstrate through the public application process?” |
“Who is difficult to work with on your team?” | “How does the team handle disagreements or competing priorities?” |
“Can you introduce me to your boss?” | “Are there other perspectives you think I should seek out?” |
“Can you review my whole resume right now?” | “Would you be open to one specific question about how I’ve described a project?” |
Compensation is a reasonable career topic; start with role-level ranges rather than someone’s private pay. A referral or introduction may also become appropriate when there is enough context. If it comes up, leave room for the person to decline and follow the employer’s process. Never press for confidential hiring material, customer details or internal documents.
How to end a coffee chat naturally
Signal the time, name one useful takeaway and make any next step optional:
“We’re almost at the 25 minutes we planned, so I’ll let you go. Your explanation of how junior analysts check their work was especially useful. I’m going to practise that in my next project. Would you be comfortable if I sent you a short update afterward?”
You do not need to ask for another meeting. If you would value another perspective, ask: “Is there a type of role or team you’d suggest I speak with next?” That lets them offer a direction without having to make an introduction.
What to send after a coffee chat
Send a short thank-you that mentions something specific. Berkeley recommends following up within one or two days, noting useful takeaways and sharing updates when you act on advice.
Thank-you example
Hi Alex, thanks for making time for coffee today. Your distinction between producing a report and explaining what someone should do with it helped me understand the analyst role. I’m going to add a short recommendations section to my class project. I appreciated hearing about your experience.
Later update, if they welcomed one
Hi Alex, a quick update on the project we discussed: I added the recommendations section and asked a classmate to challenge my assumptions. That helped me spot a gap in the analysis. Thanks again for pointing me in that direction. No reply needed—I just wanted to share what I tried.
Use these examples as a starting point and replace the details with what you actually discussed. If you promised a resource, send it along. A thank-you can simply be a thank-you; you don’t need to add another request. Give them room to reply in their own time.
Quick answers about coffee chat questions
How many questions should I prepare?
Five or six is a useful starting point. Prioritize three you most want answered and keep the others as backups. Expect follow-ups to take some of the time.
What if I have no work experience?
Say what you are studying, trying or curious about. Ask what the work involves and how you could test your interest with a small project. You do not need to present yourself as an expert.
What if there is an awkward pause?
Give the person a moment to think. Then return to something they mentioned: “You said that project changed your approach. What changed?” If the topic has run its course, move to a prepared question.
Can I ask about a job opening?
Yes, if it is relevant to the conversation. Ask about public responsibilities or the application process, and accept that the person may not know or be able to discuss it. Avoid assuming the meeting includes a recommendation or application review.
Can these questions work on a video call?
Yes. Confirm the end time, keep your list nearby and use the same short introduction and follow-ups. Ask permission before recording; brief notes may be all you need.
Bring a few questions and leave room to listen
Before your next chat, choose one goal, three priority questions and a backup opener. Afterward, write down one thing you learned and one thing you will try. That gives the conversation a practical purpose without requiring it to produce a job lead.
Questions ready? Find someone to talk to.
Maybe it’s someone doing the job you’re curious about, or someone who has made the career change you’re considering. Tell LunchME’s AI agent whom you’d like to meet. It can help you find relevant people so you can send an invitation for coffee or lunch.
Bring a few questions. See where the conversation takes you.
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