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Questions to ask in a coffee chat

By Coffee Chats · Updated

Bring three to five open questions about their path and their work that their LinkedIn profile does not answer, in order of priority, and save one closing question: who else should I talk to? One career guide suggests five to seven questions for a 30-minute chat, so three to five fits a 20-minute one 1.

Before the chat

  • Do about 15 minutes of homework. Read their LinkedIn profile, the company's site, and any recent news, and look for what you have in common 23. Never spend their time on something you could have looked up 4.
  • Practice a 60 to 90 second introduction. Who you are, what you are doing now, what you are exploring, and why you wanted to talk to them 534.
  • Have an answer for "How can I help?" Do not be surprised if they ask it, so know what you are hoping to learn 43.
  • Put your questions in priority order. If the time runs short, the important ones are already covered 3.
  • Confirm a day or two before. For a video call, make sure they have a calendar invite with the link 54.

Here is an introduction you can adapt:

Template: Your 60-second introduction

I'm a [year] at [School] studying [major]. This summer I [one relevant experience]. I'm trying to decide between [path A] and [path B], and since you've worked in [their area], I'd love to hear how you think about it.

How to run the 20 minutes

  1. 0:00 to 0:02. Thanks and small talk. Thank them, then ask how their day is going or what they are working on 6.
  2. 0:02 to 0:03. Your introduction. The 60 to 90 seconds you practiced, then hand it over to them.
  3. 0:03 to 0:16. Their story and your questions. Start with their path, then your top questions. Follow their answers instead of your list: ask for an example, say "say more about that," and avoid yes-or-no questions. Let a pause sit; as Yale's career office notes, it gives the person time to "reflect on what they said and may reveal something deeper" 7. In three studies of live conversations, people who asked more questions, especially follow-up questions, were better liked by the person they talked with, and people did not expect that effect 8. (The paper was corrected in 2025 after an independent audit, which confirmed its conclusions.) As one adviser puts it, "It's okay to go off-script too" 6.
  4. Around 0:16. A time check. Try: "I want to respect your time. We have a few minutes left." Then let them decide whether to keep going 1.
  5. 0:16 to 0:19. Next steps. Ask your closing questions (below).
  6. 0:19 to 0:20. The close. Thank them and ask if you can stay in touch 3.

Right after, write down what they said, what you promised, and who they suggested 59. Then send your thank-you the same day; the follow-up guide has a template.

If you meet in person, arrive early so you can find a table 10. On video, check your setup and find a quiet room. Do not record the call, or run an AI note-taker, without asking first 4.

Go a little deeper than "what is a typical day"

In experiments, conversations between strangers about deeper topics felt less awkward and more connecting than people expected 11. In a coffee chat, deeper means real decisions and lessons: why they chose one path over another, what surprised them, what they would do differently. It does not mean their private life.

If you want a structure, one job-search method uses TIARA: ask about Trends, Insights, Advice, Resources, and Assignments 212. A university career office suggests asking for AIR: advice, information, and referrals to other people worth talking to 13.

The questions below are written for this guide, drawing on those question banks 1713. Pick a few from different groups.

Questions about their path

  • How did you get from [your school or first job] to where you are now?
  • What made you choose [Company] when you did?
  • Which classes, jobs, or activities from college turned out to matter most?
  • What do you know now that you wish you had known in your first year of work?
  • If you were starting over, what would you do differently?

Questions about the work

  • What does a normal week look like for you right now?
  • What project is taking most of your time at the moment?
  • Which skills do you use most, and which ones surprised you?
  • What is the most rewarding part of the job, and what is the hardest?
  • What do you like least about the work?

Questions about the team and company

  • Who do you work with most, and how is your team set up?
  • What do the people who do well on your team have in common?
  • How do people early in their careers get feedback and grow here?
  • What is changing in your industry that affects your team?
  • How would you describe the culture to a friend?

Questions about breaking in

  • What is the best way for someone in my position to get an internship or a first job in this field?
  • Does your company hire on a fixed recruiting calendar or throughout the year?
  • What experience would make an application stand out to you?
  • How much do grades matter here compared with experience?
  • What is a typical starting salary range for entry-level roles in this field?
  • Which newsletters, groups, or events are worth my time?

Closing questions

  • If you were in my position, what would you do in the next month?
  • Who else should I talk to? May I mention your name when I reach out? 614
  • Is there a question I should have asked and didn't?
  • Would it be all right if I came back to you with an update, or a question, later on? 15

Questions to skip

  • What they earn. Harvard's guide says asking about the salary range you might expect at entry level is fine, but "Do NOT ask how much money the interviewee makes" 57. One career guide's question bank does ask what the person negotiated 1, but most others warn against personal pay questions, so leave that out of a first chat.
  • Anything on the company's website. Penn's career guide calls answering questions that "can easily be found online" one of "the most annoying things" for the professional 4.
  • "Can you get me a job?" Not directly, and not hinted at 5.
  • Yes-or-no questions. They end the thread you are trying to pull 7.
  • Questions about their boss or coworkers. Too personal for a first conversation 16.

FAQ

How many questions should I prepare?

Three to five for 20 minutes, in priority order, plus your closing question. One career guide suggests five to seven for 30 minutes 13.

Should I take notes?

Yes, brief ones, so you can keep listening, and fuller notes right after the chat 59. On video, never record or use an AI note-taker without asking first 4.

Can I ask about salary?

Ask about the typical range for entry-level roles in the field, not what they earn 57.

How Coffee Chats helps with this step

Before each chat, Coffee Chats prepares a one-pager on the person, with research that cites its sources, what you have in common, and questions worth asking. Your booking page checks your Google Calendar, so the time is set without a long email thread. After the call, it drafts a thank-you note and your to-dos from what was said.

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Sources

  1. Stanford Career Education (n.d.). "The Informational Interview Guide." Stanford University. https://docs.google.com/document/d/1LfRkOh7nKGDKhqaT1eUgTEybp-Omsl5gCyitldivoEo/edit
  2. Dalton, S. (2020). The 2-Hour Job Search, 2nd edition (Quick-Start Guide and TIARA graphic, publisher's bonus PDF). Ten Speed Press. https://tantor-site-assets.s3.amazonaws.com/bonus-content/N5086_2HourJob/N5086_2HourJob_BonusPDF.pdf
  3. Stanford Alumni Association (n.d.). "Build Your Network Through Career Conversations: What to Do Before, During and After." Stanford University. https://alumni.stanford.edu/career-connections/acing-the-career-conversation-what-to-do-before-during-and-after
  4. Penn Career Services (2025). "Career Guide for Graduate Students and Postdocs: Informational Interviews." University of Pennsylvania. https://cdn.uconnectlabs.com/wp-content/uploads/sites/74/2025/04/Informational-Interviews-2.pdf
  5. Harvard Mignone Center for Career Success (updated 2026). "Harvard College Guide to Making Connections." Harvard University. https://careerservices.fas.harvard.edu/resources/harvard-college-guide-to-making-connections-2/
  6. O'Keefe, S. (2021). "5 Questions to Ask During an 'Informational Interview'." Harvard Business Review. https://hbr.org/2021/10/5-questions-to-ask-during-an-informational-interview
  7. Yale Office of Career Strategy (n.d.). "Informational Interviewing." Yale University. https://ocs.yale.edu/channels/informational-interviewing/
  8. Huang, K., Yeomans, M., Brooks, A. W., Minson, J., and Gino, F. (2017). "It Doesn't Hurt to Ask: Question-Asking Increases Liking." Journal of Personality and Social Psychology, 113(3), 430-452. https://doi.org/10.1037/pspi0000097 (correction published 2025 after an independent audit that confirmed the paper's conclusions: https://doi.org/10.1037/pspi0000491)
  9. UC Berkeley Career Engagement (updated 2026). "Informational Interviews." University of California, Berkeley. https://career.berkeley.edu/start-exploring/informational-interviews/
  10. MIT CAPD (updated 2023). "Conducting Informational Interviews." Massachusetts Institute of Technology. https://capd.mit.edu/resources/conducting-informational-interviews/
  11. Kardas, M., Kumar, A., and Epley, N. (2022). "Overly Shallow?: Miscalibrated Expectations Create a Barrier to Deeper Conversation." Journal of Personality and Social Psychology, 122(3), 367-398. https://doi.org/10.1037/pspa0000281
  12. University of Nebraska-Lincoln Career Services (n.d.). "TIARA Method." University of Nebraska-Lincoln. https://careers.unl.edu/tiara-method/
  13. MIT CAPD (updated 2023). "Suggested Questions for Informational Interviewing." Massachusetts Institute of Technology. https://capd.mit.edu/resources/suggested-questions-for-informational-interviewing/
  14. Carnegie Mellon CPDC (2020). "Quick Tip Guide: Informational Interviews." Carnegie Mellon University. https://www.cmu.edu/career/documents/quick-tips/quick_tips_informational_interviews_2020_final.pdf
  15. Courtis, N., and Dalton, S. (2024). "Don't Make This Common Networking Mistake." Harvard Business Review. https://hbr.org/2024/09/dont-make-this-common-networking-mistake
  16. Bell, E. (n.d.). "How to Ask for an Informational Interview (and Get a 'Yes')." The Muse. https://www.themuse.com/advice/how-to-ask-for-an-informational-interview-and-get-a-yes