Early in my career, I received excellent advice. I was told that I must network and get to know people, and that this is the basis for a long and fulfilling career. It made perfect sense except:
I was embarrassed that I was asking for people’s time without having anything to offer in return (these were people who led teams and important projects, whose time was presumably more valuable than mine at my then career stage), and when they did graciously make the time, I didn’t know what to say, and definitely no idea how to “keep in touch” like my advisors recommended.
This post is intended as a practical guide to doing this well and building long-lived professional relationships.
It begins with preparation prior to the meeting.
Prep Questions to Ask Yourself
What do I actually want to learn or unlock? The answer cannot be “get advice”. It needs to be something specific: input on a decision you’re facing, a transition you’re considering, a blind spot you suspect you have, or maybe it’s a difficult situation you are facing. It’s a lot easier for someone to respond to a specific ask; without one, you are expecting them to invest the time to figure out what you need help with and then offer you advice.
What can I offer this person? Even junior people have something to trade. A fresh perspective, a connection to their alma mater, an introduction to someone who may become a prospective employee or customer, or an interesting data point from your world. At the minimum, bring genuine curiosity to the table. This reframes the ask from a favor to an exchange.
What’s the smallest possible ask? “Will you mentor me?” is not a small ask and definitely not one to make at the first meeting. Whether the relationship evolves to that point depends on mutual fit, ability, and interest in mentoring and being mentored, as well as practical factors like schedules. Instead, try: “May I run one decision by you?” or “What’s one thing you’d do differently?” Right-size your ask so it’s something that’s easy to respond to.
What do I already know about them? Read their recent writing, listen to a podcast appearance, learn about their background and experience. Show up at these meetings with context and having done your homework.
What’s my one-sentence intro? Have a crisp answer ready for “so tell me about yourself”. It should mention your role, what you’re working on, where you are headed (if relevant), and why this conversation matters to you right now.
What’s the ideal outcome? Decide in advance whether you want advice, a connection, a sounding board, or just to build the relationship. This will inform how you spend the time with them.
How much time do I actually have? Confirm and respect the window; don’t assume 30 minutes unless they’ve said so explicitly.
During the Conversation
Plan to spend roughly 70% of the time listening, 20% sharing, and 10% on the ask. I cannot emphasize enough how important it is to spend the bulk of the time in active listening mode rather than talking mode.
Be sure to ask open questions, and let them talk about their path and current thinking. Share enough about yourself so it’s a real exchange and doesn't feel like an interview. Land your specific ask clearly, usually near the end.
Here are some great questions to ask:
“What’s something you believed before in your career that you no longer believe?”
“What would you do in my position right now?”
“Who else should I be talking to?” Never leave a coffee chat without asking this. This is what turns one conversation into a chain.
“What’s a mistake you see people at my level making that they don’t realize?”
“What’s the hardest part of your role that people don’t see from the outside?”
“If you were starting over in this industry today, what would you do differently?”
“What’s a resource, book, or habit that’s shaped how you think?”
“What question should I be asking that I haven’t?”
During the meeting:
Take notes visibly (or ask permission to). It signals you value what they’re saying and helps you actually remember it.
Keep track of time. Don’t make them be the one to end the meeting.
Leave plenty of room for tangential topics. Some of the best insights come from unstructured moments, not from scripted questions.
If you have an ask (intro, feedback on something, a job lead), read the room for whether this meeting is the right moment or if a follow-up email is better. Each has its pros and cons, so reading the room is critical.
After the Conversation
Close the loop. Do send a specific thank-you within 48 hours and reference one concrete thing you’re going to do differently, not just “great chat.”
If they gave you a referral or resource, follow up on it and report back. This is what makes people want to help you again. People are happy to help when they see it was genuinely valued and followed through on.
Add them to a light-touch update cadence. A quarterly “here’s what happened since we talked” note instead of going quiet until you need something again.
Look for a way to reciprocate, even if small. Send them an article relevant to something they mentioned, offer to make an introduction of your own, or share something useful you think may be of interest to them.
If they offered an introduction, make it easy for them. Be sure to draft an intro email that they can forward or copy and paste into their note. Don’t make them write it from scratch.
Most of the compounding value of a coffee chat lives in the follow-up. A single great conversation is worth a lot, but a relationship that gets touched every few months for years is invaluable.