Someone has agreed to spend part of their afternoon talking with you. Maybe they work in a field you are considering, have built something you admire, or were introduced by a mutual friend. The calendar invitation says “coffee,” which makes the meeting sound wonderfully informal until you sit down to prepare and discover that “ask good questions” is your entire plan.
A little preparation makes the conversation easier for both of you. It gives the other person a sense of what would help, and it stops you spending the whole meeting trying to think of your next question. You do not need a script for every minute. You need a clear reason for meeting, a few questions grounded in their experience, and enough room to follow an answer somewhere interesting.
The short answer
Choose one thing you want to understand, read a small amount of relevant background, and prepare three questions. At the start, check the time available and explain your aim. At the end, confirm anything you offered to do and thank them for something specific you learned.
Choose a purpose small enough for one conversation
“Learn about product management” could fill a university course. “Understand how a product manager decides what to work on in a small team” gives a conversation a useful shape. Think about the decision you are trying to make or the part of the work you cannot see from the outside. Your contact can then answer from experience rather than trying to summarize an entire profession over a cooling cappuccino.
For an informational interview, be honest that you are exploring and learning. If your real request is a referral, job opportunity, partnership or feedback on a proposal, say so before the meeting rather than quietly changing the purpose once someone has arrived. They may still be happy to help, but they should be able to choose the conversation they are agreeing to.
A fictional purpose statement
I’m comparing customer research and product operations roles. I’d like to understand how you divide your week between talking to customers, analyzing what you hear, and helping the team act on it.
Read enough to ask a better question
Start with information the person has chosen to share in a professional setting: their current role, an article they wrote, a recent project, or the organization’s description of its work. Look for one relevant detail that helps explain why you asked them. A person’s public profile is a starting point, and it may be out of date; leave room for them to correct your understanding.
Avoid collecting personal details simply because they are easy to find. The goal is to understand their work, not to surprise them with how much of their life you have reconstructed. If a mutual contact shared context privately, do not treat that as material you can repeat in the meeting. Keep your preparation tied to the reason you are speaking.
Write down what you already know beside what you want to learn. If their website clearly explains the service their company sells, use the meeting to ask about a decision behind it or a challenge of delivering it. This gives their experience somewhere useful to enter the discussion.
Make a one-page prep sheet
The sheet below is deliberately small. You should be able to glance at it before the meeting and remember why you are there. The example is fictional, and the same structure works for a student exploring a career or a founder learning from someone who has handled a similar operational problem.
Coffee-chat prep sheet
Person and context: Priya, introduced by Leo; works in customer research. Check her current role rather than assuming the profile is current.
My question: Would I enjoy the day-to-day work of customer research?
What I already read: Her public write-up of a research project.
Three questions: What does an ordinary week involve? How do you decide which customer questions deserve investigation? What part of the role surprised you when you started?
One example I can explain: A small interview project from my course, if relevant.
Boundary: We agreed to 20 minutes. I will check before extending it.
Afterward: Write down what changed my understanding and any resource I promised to send.
Keep additional questions in reserve rather than working through them like a questionnaire. If an answer opens up something valuable, follow it. “Could you walk me through a recent example?” will often be more useful than immediately jumping to the next item on your list.
Make the opening easy, then listen
A simple opening helps the other person settle into the conversation. Thank them, check the time available, and explain your purpose in a sentence or two. You can mention the piece of their work that made you want to speak, as long as the interest is genuine. There is no need to deliver your entire biography before they get a turn.
A fictional opening
Thanks for making the time. Does 20 minutes still work for you? I’m exploring customer research roles and was interested in the project you wrote about. I’d love to understand how you decide what to investigate and what the work is like between interviews.
Ask whether they are comfortable with you taking a few notes. Keep those notes brief enough that you remain in the conversation, and avoid recording audio unless you have explicitly agreed on it. If you want a fuller personal record, you can write or dictate your own recollection after the meeting.
Close with what you learned and what happens next
As the agreed time approaches, say what helped you and check any next step. If they offered an article, you can note the title rather than turning the offer into an urgent assignment. If you offered something, make sure it is specific enough to complete. “I’ll send the public workshop page we discussed” is easier to act on than “I’ll send some useful stuff.”
A short thank-you can name one idea that changed your thinking. Later, if you use their advice, a genuine update can give the connection a natural reason to continue. Neither message needs to include a new request. They gave you their perspective; showing what you did with it can be enough.
Keep the prep sheet and your eventual notes together so that you can distinguish what you expected from what you actually learned. In Kontextual, contacts, notes and follow-up reminders can hold that context and your own commitments. The useful outcome of this meeting may be a clearer decision rather than a second meeting, and that still makes it time well spent.
Sources and scope
- UC Berkeley Career Engagement: informational interviews
Background on preparing questions, respecting the agreed time, and following through after an informational interview. The examples and prep sheet here are original.