The latte is half gone and you've worked through the coffee chat questions you wrote down on the train. They answered every one. It was pleasant, even useful. And yet when you get up to leave, it feels like you conducted a survey rather than met a person.
The questions weren't the problem. What happened after each answer was.
The best coffee chat questions are rarely the first question you ask. They're the second one: a follow-up that proves you heard the answer.
This guide is organized around what you're trying to learn about the person, with examples for each. But the most important section is the one about follow-ups, because that's where the research points.
Karen Huang and colleagues at Harvard studied hundreds of conversations, online chats and in-person speed dates, in It Doesn't Hurt to Ask: Question-Asking Increases Liking, a 2017 paper. People who asked more questions were liked more by their partners. The effect came mostly from one type: follow-up questions, the ones that ask someone to say more about what they just said.
The researchers sorted questions into categories. Introductory questions open a conversation. Full switches jump to a new topic. Mirror questions bounce back a question you were just asked ("Good, and you?"). Follow-ups stay with what the other person said. Only follow-ups reliably signaled that the asker was listening and cared, and that perception of responsiveness is what drove liking.
They also analyzed speed-dating conversations. People who asked more follow-up questions were asked on more second dates. An 8% difference in follow-up rates was associated with about one additional second date over an evening of 20 speed dates. The authors are careful to note this is a correlation, but the pattern is hard to ignore. Most striking of all, the people in their studies didn't predict any of this. They didn't expect asking questions to make them more likable.
There's a deeper reason it works. Diana Tamir and Jason Mitchell at Harvard found that people spend roughly 30 to 40% of their speech telling others about their own experiences, and that talking about yourself activates the brain's reward system. In one study, participants gave up money for the chance to talk about themselves. A good question gives someone something they already enjoy. A good follow-up tells them you enjoyed it too.
Start in the present. Someone's current problem tells you more about them than their resume, and it's also where you might eventually be useful.
These work because they're specific without being intrusive. They invite an honest answer instead of a polished one. "What's taking up more of your week than you expected" almost always gets a real story, because everyone has one.
Before you go, it helps to know what you already know about them. If you've met before or emailed, a quick look at the last conversation keeps you from asking something they already told you. We've written about preparing to see someone again.
Goodword gives you the context on someone before you sit down with them, so your questions can start where your last conversation ended. Start your free trial.
Career-path questions are where most coffee chats go flat, because "walk me through your background" gets the LinkedIn summary read aloud. Ask about the turns instead of the timeline.
"What did you almost do instead" is one of the most reliable questions in this whole list. It skips past the official story and gets at what they value and what they gave up. The question about who took a chance on them tends to bring out gratitude, which changes the tone of a conversation for the better, and it often tells you how they think about helping others.
A relationship gets traction when each person learns how they might help the other. You don't need to ask about this directly; you need questions that let it come up.
The first question surfaces needs. The other two surface what they're proud of and what they'd be glad to share. Listen for both. If they mention they're struggling to hire a designer and you know a great one, that's your follow-up, and it matters more than any thank-you note. It's the move we describe in our argument for being the first to give.
None of the questions above are worth much without this part. Once someone answers, stay with the answer. A few follow-ups that work almost anywhere:
Notice the third one. The most powerful follow-ups quote the person back to themselves. When you pick up a detail they mentioned in passing, you show that you heard more than they expected you to.
A good rule is to ask at least one follow-up before you change topics. Resist the urge to tell your own related story right away. Your story can come later. When it does, it lands better because they've already felt heard.
Some questions undercut the whole meeting.
Anything their public profile answers. "So where did you go to school?" tells them you didn't prepare.
The disguised ask. "Do you know anyone hiring?" in the first meeting turns a generous half hour into a transaction.
"Can I pick your brain?" It isn't a question about them. It's a request for free consulting with a friendly label.
Questions you ask only to sound smart. If you wouldn't care about the answer, they'll be able to tell.
Rapid-fire lists. Ten questions in thirty minutes leaves no room for follow-ups, which, as the research shows, is where the liking comes from.
The last question should look forward. Two good ones:
The second one does something the first can't. It assumes there will be a next time, and it gives you a natural reason to check in. Write down the answer, whether in a notebook or in a relationship copilot like Goodword. It's the opening line of your next message, and capturing the right details afterward is what makes it possible.
The difference between a coffee chat that goes nowhere and one that starts something real is rarely the quality of the list you brought. It's whether the other person left feeling understood. Bring a few good questions, then let their answers decide what you ask next.
Goodword holds on to what people told you over coffee, so your next message picks up the thread instead of starting over. Give Goodword a try.
Prepare four or five, and expect to use two or three. Most of the conversation should come from follow-ups to their answers rather than from your list. If you get through every prepared question, you probably moved on from answers too quickly.
A follow-up question asks the other person to elaborate on something they just said, like "What made that decision hard?" Research on live conversations found follow-ups are the type of question most strongly linked to being liked, because they signal you were listening. They also tend to produce the most interesting answers.
A few questions on your phone or a small notebook is fine, especially if you glance at them before you sit down. Reading questions off a page during the conversation makes it feel like an interview. Jot down a word or two if something important comes up, and write fuller notes right after you leave.
Questions about someone's choices, motivations, and what they find hard are personal in a good way and usually welcome. Avoid questions about health, family plans, salary, or anything they haven't raised themselves. If they open a door, it's fine to walk through it gently.
Ask about judgment calls that come with their scope, such as "What tells you a team is ready for more autonomy?" Senior people get asked about their career path constantly and are asked about their thinking far less. Keep confidential strategy out of it unless they bring it up.
Answer honestly and with some depth, then turn it back with a question about something they said earlier. A conversation where both people share is the goal. If they're more interested in your story, that's often a sign they're deciding how they might help you.
