How to Turn a Coffee Chat Into a Conversation

There's a specific kind of dread that creeps in about ten minutes into a coffee chat. The small talk is done. You've delivered your introduction, they've walked through theirs, and now there's a long stretch of call still ahead of you and a quiet voice in the back of your head asking the same thing on a loop: what do I say next? For the last twenty minutes you're not really networking anymore. You're just trying to keep the conversation alive, and barely managing it.

I know that silence well. Across my own recruiting I did more than 300 coffee chats. Since then I've listened to over 150 of my students' chats, and I've been on the other side as the person being coffee-chatted more than 50 times. For years I heard the advice everyone hears: "don't treat it like a Q&A, have a conversation." And for just as long I nodded along without ever finding a solid explanation of what actually separates the two. It sounds obvious right up until you're the one sitting in the dead air.

So let's fix that. This is the difference between a chat that fizzles and one that flows, broken down into mechanics you can actually practice.

First, diagnose it: are you having a Q&A or a conversation?

The cleanest way I've found to tell the two apart is to measure who's doing the talking, specifically the talking time after the small talk and TMAY exchange are over. That early stretch where you make small talk and trade introductions doesn't count. What counts is everything after, the part where you're asking questions and they're answering.

Q&A = past the small talk and TMAY exchange, they talk >80% of the time.

Conversation = past that same point, the talking time is split 60–70% them, 30–40% you.

Sounds simple, and it is. The hard part was never identifying whether your chats are Q&As or conversations. The hard part is actually having the conversation. But you can't fix a problem until you've come face to face with it, so here's your homework: the next time you have a coffee chat, record it and clock the talking times for both of you. You're not going to take action until you see the problem laid out in front of you. If you're consistently sitting at an 80/20 split, you're running Q&As, and a Q&A will never get you a referral.

The real problem isn't "talk more," it's "what to talk about"

Here's where most advice goes wrong. People hear "30 to 40% of the talking should be yours" and conclude the fix is simply to talk more. It isn't. There are only so many things you can say, and remember, we're measuring the stretch past those first few minutes, the part where they're answering your questions. If you just talk more to fill airtime, you're not listening anymore.

Picture it. They're telling you about the deals they're working on, and you respond with your thoughts on Jerome Powell's latest speech. You might be splitting the microphone a clean 50/50, but this is a conversation you do not want to have. You hijacked the topic. So talking more isn't the goal. Staying on their topic while still holding up your share of the talking is.

That's the real bind. You have to stay on-topic, but you also have very little control over what the topic is. If you just ask them to clarify what they said, you imply you don't understand their job. If you simply acknowledge their point and move on, you signal that you either weren't really listening or you're steering toward more comfortable territory for yourself. Neither is the impression you want to leave.

The way out of that bind is a specific move, and it's the heart of this whole thing.

The core move: summarize, then relate or clarify, then ask

Instead of jumping straight into your next question, do this first: demonstrate that you actually understood their point. If they talked for two minutes, summarize what they said in under 25% of that time, so roughly 30 seconds here. Then do one of two things. Either relate their point to a past experience of your own, or raise the specific point you wanted to clarify.

If you relate it to your own experience, use that experience as the bridge into your next question, one that connects to what they just said but still nudges the conversation forward. If instead you're clarifying, either say what you expect their answer to be or walk them through your thinking before you ask.

Those are the two shapes every strong coffee chat response takes:

Their (2-minute) Answer > Your (~30 second) Summary > Your Past Experience > Your Next Question

Their (2-minute) Answer > Your (~30 second) Summary > Point to Clarify > Your Thought Process / What You Expect Them To Say > Your Next Question

Done right, this stretches your response to about 30 to 40% of the talking time, which is exactly the conversation threshold. And notice you don't have to say anything brilliant to get there. You need to be polite, show you understood, and ask a relevant question right after. The difficulty isn't any single piece. It's doing all of them at once: listening, building your response, pulling up a relevant experience, and organizing your thoughts in real time.

Turn "simple" questions into "complex" ones

Another way to see the same move is as a spectrum that every coffee chat question falls on. On the left sit simple, non-targeted questions. On the right sit complex, targeted ones, built out with either a walkthrough of your thought process or a story from your own experience. The whole game is to drag your questions from the left side to the right.

Here's what the left side looks like, three perfectly ordinary simple questions:

What was the biggest challenge you faced going full-time in Investment Banking

What's your team structure like?

What's the culture like at your firm?

There's nothing wrong with these on their own. They're just bare. There are two ways to make a simple question complex.

Method one: Create a Statement. Wrap the question in your thought process or what you expect them to say. Here's that first simple question, the one about the biggest challenge, rebuilt this way:

From the analysts I've talked to, the consensus is that the hardest part of going full-time isn't the technicals at all – it's calibration, learning what good enough looks like for each person you work for. I've been trying to build that muscle by asking for feedback in my club projects the way I would on a desk. Out of curiosity, when you transitioned from intern to full-time, was figuring out everyone's standards the biggest challenge, or was it something more concrete, like the workload itself?

Method two: Craft a Story. Lead with a relevant experience of your own, then ask. Same underlying question, the biggest challenge, told the second way:

My summer at a regional M&A shop started rough – the learning curve on comps and CIPs was steeper than anything school had thrown at me, and for the first month I was the slowest person on every task. It clicked eventually, and by August I was running the first drafts myself. My Associate's take was that the curve never really ends, it just changes shape, which stuck with me. So I wanted to ask: in your own move from student to full-timer, what was the biggest challenge – and what did you underestimate as an intern that you only appreciated once you returned?

Same bare question underneath, two completely different textures on top. Both give the other person something to react to instead of a cold prompt. And that's the quiet benefit of turning simple into complex: a complex question hands the listener boundaries for their answer, which lets them be more specific and more nuanced. It shows you've put yourself in their shoes, that you were actually listening, and that you genuinely care about their perspective.

A worked example: the same exchange, two different ways

Let me show you what this sounds like in a real chat. This is from a conversation one of my students had with a 1st-year Associate on Bank of America's Technology team in NYC, who happened to have a background as a professionally trained concert pianist. Here's how the exchange went.

Her answer ran long and generous: a concert-piano past, two years as an analyst, the jump to Associate on the Technology team, a market hot enough to keep her buried in deals. The student's response did exactly what this article teaches – summarized her story, related it to his own piano training, and asked about the pianist chapter first. The full exchange is in how to stand out in a coffee chat.

Look at what he did. He summarized so she felt heard, related a genuine piece of his own background, the piano, and then segued into his next question. Most students would have skated right past the pianist detail, but he stopped the conversation to double-click on it, because he understood it was the single best opportunity to build rapport on that call. I'd bet the moment he paused on it, that Associate realized she wasn't talking to an average student. And if he'd blown past it, there might not have been another opening in the whole chat to score those "personality" points.

Now compare it to the version most students would give:

"Got it, thank you for the background. What was it like to be a professional pianist?"

This isn't a disaster. It wouldn't kill his chances at a referral on its own. But by skipping the summary and leaving out his own experience with piano, he'd fall behind any student who included them. Same question, far less rapport.

Here's a second stretch of that same chat, because it teaches one more thing. The Associate explained how her team was structured.

Two Associates, no VPs, one Director – "act like a VP," they were told: lead the calls, hold the pen. The student summarized that structure back to her, noted it didn't match anything he'd seen at his boutique, and asked – before finishing his own reasoning – "was it always structured this way?" Her full answer, and his complete wind-up, are in coffee chat questions to ask in IB.

Notice he actually asked his question ("was it always structured this way?") before he walked her through his reasoning about how it came to be. That's fine. Past your summary of their point, the exact order of what you say barely matters, as long as you're coherent and they can follow the question. In both responses he stretched himself to roughly 30 to 40% of the talking time, where most students would acknowledge and move on. You don't need to be revolutionary. You need to be present.

Two kinds of questions that keep it going

Once you can build complex questions, it helps to know what you're building them for. Coffee chat questions come in two types, and a good chat uses both.

Interview Ammunition. These are the questions aimed at improving your own behavioral answers, the exact reasons, phrases, and framing that make up a strong response, plus the context they're delivered in. You obviously can't ask a professional a behavioral question the way an interviewer would ask you, so you use the simple-to-complex move to bridge the gap. The payoff is real: professionals in the same role tend to give many of the same points to the most common behavioral questions, and those are points that worked, because the people giving them are the ones who broke in. Here's how I'd quietly convert the classics:

• "Why [banking]?" → "Why did you end up choosing [banking] over [consulting]?"

• "Why this team / firm?" → "What drew you to the team you're currently on?"

• "Why should we pick you?" → "What traits are common among the top analysts?"

• "Where do you see yourself in 5 / 10 / 15 years?" → "Have you thought about what you want to do after [banking]?"

Rapport-building. If Interview Ammunition questions are the "selfish" ones, the answers help you, rapport-building questions are the "selfless" ones, the questions someone actually enjoys answering. They fill the gaps that ammunition questions leave. A good rule is to aim at whatever that person is likely proud of:

• An analyst might like talking about their recruitment journey and how they got to where they are today.
• An associate might like talking about their first big deal or project, or what earned them their promotion.
• A VP might like talking about the first deal or project they ran point on.
• A Director might like talking about the first big client they landed.

How do you know if it's working? Don't try to read tea leaves from their tone. The most reliable tell is simply the length of their answers. The longer they talk, the more engaged they are. But you don't know what kind of day they're having, so read the room and treat all of this as something to experiment with, not gospel.

The small mechanics that quietly decide it

Once the core move is in place, a handful of small habits separate a smooth chat from a clumsy one.

Vary your acknowledgements. This one is low-hanging fruit and weirdly easy to neglect. When every single response out of your mouth is "got it… got it… got it," you sound like you've checked out, even when you're genuinely engaged and simply forgot to change the word. That third case, interested but on autopilot, is the one most students fall into, and the professional can't tell the difference. Keep a few on hand and rotate them:

"got it", "that makes sense", "thank you for that", "okay", "sounds good"

I literally kept five of these on my screen during chats so I could glance up and grab a different one without spending any real brainpower on it.

Mind the placement of your impressive questions. You know the line in restaurants, "location, location, location," the idea that where the restaurant sits matters more than the food it serves. Coffee chats are the same. Your sharp, knowledgeable question is the food. But its quality only lands if the location is right, and in a chat, location means when you ask it: how related is it to what they just said? A great question dropped at the wrong moment lands like a non-sequitur. Fair warning, this is the part that takes the most reps. You'll only really get the timing right after you've done somewhere north of 10 to 20 chats. A game only gets fun once you've learned its rules, so pay down that "ignorance debt" as fast as you can.

While we're on questions that erode rapport, two archetypes do the most damage:

The Absolute. Describing someone's world back to them in absolutes, as if you know it better than they do, makes you sound like a know-it-all with no self-awareness:

"I saw you went from Audit into Investment Banking, and I'm sure you were planning that exit from your first week, as most auditors are, and you must be enjoying finally building models instead of ticking boxes. Did you ever consider Corporate Development?"

The problem is it leaves no room for an alternative, or frames any alternative as abnormal. The tone is prescriptive ("you should've done this") when it should be inquisitive ("you did this, here's why I think you did, but I'd love your perspective").

The Show-off. The question engineered to broadcast how much you know:

"Seeing as you're in the Consumer group at the Central Bank of Fiji, what's your view on the run-up in cocoa prices caused by the export licensing rules just adopted by the 4 dominant West African growers – Ivory Coast, Ghana, Nigeria & Cameroon – particularly with the ICCO warning about structural deficits after that long FT piece on chocolate inflation – have you seen that one?"

It's exaggerated to make the point, but you can probably hear traces of your own convoluted questions in it. Trust me, the show-off intent is always obvious, and it erodes whatever rapport you'd built.

Recovering from an awkward pause. It happens. You accidentally ask a yes/no question, they answer in three words, and the silence yawns open. Don't panic. Just circle back to something they mentioned earlier:

"[awkward pause]...Yeah, so I remember you mentioning you're one of only a handful of analysts on your team, what is that like? I assume the team being more top-heavy would provide for a lot of mentorship opportunities?"

This same move rescues you if the chat is bone-dry and you've burned through your prepared questions before the fifteen-minute mark. Though candidly, if that keeps happening, either you've got more reps to put in or the other person was pressured into taking the call.

Make your questions feel related: follow the chronology of their intro

There's one more technique that quietly produces on-topic, related questions, and it solves the "what do I talk about" problem at the source. The structure to follow is the same one the other person follows when they introduce themselves.

Think about it. The person across from you is a full-time professional, which means they've refined their own introduction down to the points they consider most important and most impressive. So it makes sense to build your questions around exactly those points. As they introduce themselves, listen for the timeline buried in it and note the "chapters." Common ones are pre-college (often a sport or activity they did at a high level), college (the finance catalyst, clubs, recruiting, internships), and post-college (first full-time role, "figuring it out," current firm). For senior bankers, add their twenties (career switches, a notable accomplishment, moving countries).

Use those chapters as buckets for your questions. Bucketing this way does two things at once: it makes turning a simple question into a complex one far easier, because you already have the relevant context, and it makes your questions feel related to one another instead of scattered. When you hop randomly between unrelated topics, you make the other person feel unheard and build zero rapport. When your questions track the shape of their own story, they can't quite put their finger on why, but the whole thing just feels organized, and that organization rubs off on how they see you.

Why this takes reps, and how to free up the bandwidth

If all of this sounds like a lot to juggle in real time, that's because it is. Let me give you the mental model I use.

Say you have 10 units of mental processing power. In a chat, that capacity gets spent on two things: crafting a relevant question, and responding to what they just said. Here's the trap. If you pour all 10 units into crafting your next question, you have nothing left to actually respond, so you just acknowledge their answer and move on. That's a Q&A. And it's exactly what happens to most students, not because they're lazy, but because the stakes feel enormous and they haven't done enough chats to build the question and the response at the same time.

This is why preparing a list of personalized questions before the chat matters so much. It's not really about the questions themselves. It's that having them ready takes the entire "invent a question on the spot" load off your plate, which frees up those units to do the thing that actually earns referrals: responding well. I'd prepare 5 to 10 personalized questions before each chat and expect to ask only 1 or 2 of them. The point isn't the catalog. It's the freed bandwidth.

One tactical habit helps even more: the instant a good question pops into your head mid-chat, write it down. As someone talks, your brain throws up a whirlwind of thoughts, and a genuinely insightful question will surface and then sink right back into the noise if you don't catch it. Jot it down immediately. Don't stop to judge whether it's any good. Do that later, as they're wrapping up their answer and you can afford to pay a little less attention to them and a little more to what you'll say next.

And don't be discouraged if the first chats feel impossible. Knowing when to jump in and how long to talk is not something you can read your way into. It comes from direct reps, because a coffee chat is unlike any conversation you have with friends or family. Acclimating to that setting is the prerequisite for everything above: the comfort to share a view of your own, build on theirs, and bring the two together cleanly. I was deeply introverted and genuinely bad at this when I started, fifteen-second-awkward-silence bad. The only reason I got good was volume.

Two things sit just outside this article but feed directly into it, and they each deserve their own deep dive: nailing your introduction, the TMAY that sets the lens the professional sees you through, and the craft of preparing personalized questions in the first place. Sharpen those two and the conversation itself gets dramatically easier, because you walk in with the tone already set and the bandwidth already freed.

Master the move at the center of all this, summarize, relate or clarify, then ask, and you stop dreading the stretch where the small talk runs out. That's the whole flip. A Q&A is them talking while you wait for your turn. A conversation is two people building on each other. The mechanics are learnable. They just take reps.