There’s a particular kind of message most of us have received, and some of us have sent. It opens with “I hope this finds you well.” It mentions your “impressive journey.” It asks for “just 15 minutes to pick your brain.” And it lands with a small thud, because it reads like what it is: a template, sent to you and probably eleven other people, by someone who wants something they haven’t quite named.
Knowing how to ask someone for a coffee chat, a real one that gets a yes and turns into a conversation worth having, is a quieter skill than the templates suggest. It’s not about the perfect subject line. It’s about asking a specific person a specific thing, in a way that’s easy to say yes to. Here’s how to do it without the cringe, and what to do once you’re actually sitting down.
Why networking feels gross (and when it doesn’t)
The discomfort isn’t just in your head. A 2014 paper in Administrative Science Quarterly by Tiziana Casciaro, Francesca Gino and Maryam Kouchaki (titled, wonderfully, “The Contaminating Effects of Building Instrumental Ties: How Networking Can Make Us Feel Dirty”) found that networking done purely to advance your own career can leave people feeling morally grubby in an oddly literal way. In their experiments, thinking about instrumental networking made cleansing-related concepts more mentally accessible, as if part of the brain wanted a shower. A companion survey of lawyers at a large North American firm found that the professionals who felt dirtiest about networking did it least. (Researchers have debated parts of the evidence since, but the core observation survives everyday testing: extraction dressed up as friendliness feels bad from both sides of the table.)
The useful detail is what didn’t feel dirty. Connecting with people out of genuine interest, for friendship or for support, carried none of the same ick. Which suggests the problem was never the coffee, or even the ambition. It’s the pretence. A warm coffee chat, where you’re honestly curious about the person and clear about why you’re asking, sits on the right side of that line. A templated “value-add touchpoint” does not.
Start warm: the people you already half-know
The templates go wrong at the first step, by pointing you at strangers. The better first move is usually someone you already know, or used to.
In a study published in Organization Science in 2011, Daniel Levin, Jorge Walter and J. Keith Murnighan asked hundreds of executives to do something most found mildly terrifying: reconnect with people they’d been out of touch with for at least three years and ask their advice on a live work problem. The executives expected awkwardness. What they got was some of the most valuable input in the whole exercise. Advice from these “dormant ties” was rated as useful as, and often more useful than, advice from current contacts, and it took less time to get. The researchers’ explanation, laid out in MIT Sloan Management Review, is that an old connection keeps the trust of a strong tie while the years apart fill it with the fresh perspective of a weak one. The relationship isn’t dead. It’s dormant, and it wakes faster than you’d think.
So before you draft a cold message to a stranger with an impressive title, scroll back. The former colleague who moved into the industry you’re curious about. The uni friend now three suburbs and one career away. “It’s been ages. Can I buy you a coffee and hear about the move?” is the easiest networking message ever written, because it barely is one.
How to actually ask
When you do reach out, warm or cold, a few rules keep the ask on the human side of the line. Alison Green, who has fielded workplace questions at Ask a Manager for nearly two decades, points out that the coffee itself was never the draw: it’s a social nicety, not the reason anyone says yes. People agree to these conversations when the request is clear, small, and shows the asker has done some thinking. Her practical tip from that same piece: put a couple of your actual questions in the first message, so the other person can see the conversation will go somewhere.
She’s also blunt, in an interview with Marketplace, about the phrase everyone reaches for: “can I pick your brain” is vague, and vague is the problem. It hands the other person all the work of figuring out what you want, how long it will take, and whether they’re even the right person to give it.
A good ask does that work for them. Something like: “I’m a primary teacher looking at a move into instructional design, and your name keeps coming up. Would you have 25 minutes for a coffee in the next few weeks? Two things I’d love to ask about: how you handled the jump from the classroom, and what you’d want to see in a first portfolio. Happy to come to wherever’s easy for you, and no worries at all if you’re slammed.”
Notice what’s doing the lifting. Why them, specifically. A time cap, and a modest one. The questions, up front. Their convenience, not yours. And a graceful exit, because an ask that’s easy to decline is also easier to accept. One more rule, which we’ve written about properly elsewhere: if you did the asking, the coffee’s yours to shout.
Once you’re sitting down
The sit-down is the easy part, if you remember what it’s for. The career experts in Harvard Business Review’s guide to informational interviews keep circling the same principle: you’re there to learn, not to pitch. Rebecca Knight’s summary of the advice is to think like a journalist: ask, listen, follow the interesting thread, take the odd note. The UK career strategist John Lees offers a five-question spine that will carry almost any coffee chat: how did you get into this line of work, what do you enjoy about it, what’s not so great, what’s changing in the sector, and what kind of people do well in it. You won’t need all five. Two, asked with genuine curiosity, usually open the rest.
And don’t ask for a job. Not because it’s forbidden, but because it retroactively rewrites the conversation into the thing you promised it wasn’t. If the person likes you and hears of something, they’ll say so. The visibility alone, as Lees notes in the same piece, can quietly move you onto a shortlist. Respect the time cap you named, close warmly, and send a short thank-you within a day that mentions one specific thing from the conversation. Then let it breathe.
The first one is the worst one
If all of this still feels excruciating, there’s comfort in the research: the discomfort is front-loaded. A 2023 paper by Adam Kanar at Brock University, published in The Career Development Quarterly, ran two studies in which university students conducted a single informational interview with a working professional. Compared with students who didn’t, the ones who did came out the other side with measurably higher networking self-efficacy: the belief that they could do this sort of thing, and do it well. One conversation moved the needle. The skill isn’t charisma. It’s reps.
That’s the honest version of networking: not a room full of lanyards, not a template with someone’s name mail-merged in. One person, asked plainly, about something you actually want to know. It’s also, not coincidentally, the shape Flat White is built around. The app’s networking mode matches you with one person for one coffee, both of you already opted in, so the hardest part of the whole exercise, the cold ask, is done before anyone’s ordered.
Meet one person. Over coffee. On purpose.
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