The Questions That Win an Investment Banking Coffee Chat

A student of mine was a few minutes into a call with an Associate from Bank of America's New York Technology team. She had just finished introducing herself, and buried in the middle of her answer was a detail most students would have walked right past: before banking, she had trained as a concert pianist.

Here is what she actually said:

"…have a background in piano performance and was professionally trained as a concert pianist. I'm a 1st-year associate and did my 2 years as an analyst, I'm coming up on the end of my 1st-year as an Associate and am part of the Technology team here in NYC. I would tell you that when I started as an intern, you know, I was exposed to the culture at BofA – it's a great culture that provided a great learning experience… – and then as a full-timer I came in and had a ton more responsibility and wanted to make sure I was learning & growing. The more reps I got on deals the better I got, so when I joined I was lucky that the market was crazy and the tech market in particular was booming…so there were quite a few deals I was on. In a nutshell, it's been great – the people are amazing & very generous with their time, especially when you want to learn something or have questions. So yeah, I'll pause there in case you have any questions."

Most students hear an answer like that and reach for the most efficient possible reply:

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

My student did something different:

"Got it, thank you again for taking the time to speak with me. I really appreciate the personal background as well and I think it's really cool how you ended up in Investment Banking. Funnily enough, when I was growing up I played piano as well but, of course, never was good enough to go professional – I think I made it to the Certificate of Merit advanced level before stopping but really enjoyed that experience. Before getting into the more job-related questions, I was curious to hear what it was like to be a professional pianist and how that journey was?"

Look at what he did. He summarized her answer so she felt heard. He connected it to a real piece of his own background, the piano and the Certificate of Merit advanced level. Only then did he ask his question. The version most students would have given is not wrong, exactly. It would not have eliminated his chances at a referral. But by dropping the summary of her introduction and saying nothing about his own experience with piano, it would have put him behind any student who included both. And the instant he paused to dwell on the piano instead of racing past it, that Associate realized she wasn't talking to an average student.

That is what a well-built, well-placed question does, and it is the entire subject of this guide. Across 300+ of my own coffee chats, 150+ chats I have sat in on with my students, and the 50+ times I have been coffee chatted myself, I have watched the questions a student asks do more to earn or kill a referral than almost anything else they say. So let's go deep on how to build them.

Every Question Should Be Looking for an Opinion

Underneath everything else in this guide sits one principle, so start here: your coffee chat questions should always be looking for an opinion.

The fastest way to break that rule is to ask a Yes/No question. Doing this will immediately turn any coffee chat into a Q&A, the one thing we desperately want to avoid. Beyond interrupting the flow of the conversation, a Yes/No question positions you as someone who didn't do their research, comes off as lazy and uninterested, and will often frustrate the other person.

Here is why it lands so badly. Yes/No questions are almost always ones you can confidently find the answer to online, or, with where AI is today, using ChatGPT or some other generative AI chatbot. And if you can find it online, why are you asking a professional? In their mind, there are only two explanations, and both hurt you.

The first is that you didn't look online and were simply lazy. This is very avoidable, and it is part of the reason you should prepare your questions before a chat. If you try to find the answers beforehand, you will discover what is online and what is not, which lets you refocus your questions on the latter.

The second, more common explanation is that a piece of the information was genuinely missing from what is online: a professional's unique perspective, an applied understanding of what you read, or some combination of the two. The problem is that if you don't show them the research you did, they will assume you did none. This is exactly why walking them through your thought process, or outlining what you expect their answer to be, is so powerful. Doing that before you ask the question benefits both of you. They understand where you are coming from, and you look well-researched and prepared.

There is one narrow exception. If you genuinely need to clarify something, you can ask a Yes/No question, but this is usually done when you have a much larger question to ask and you want to make sure it is framed correctly before passing the microphone back. Used that way, the Yes/No is scaffolding for an opinion-seeking question, not a substitute for one.

And if you slip and ask a flat Yes/No that produces one of those awful silences, don't panic. The recovery is simple: circle back to a point they raised earlier.

"[awkward pause]…Actually, going back to something you said – you mentioned your group just went through a reorg, how has that landed? I'd assume the shuffle changed who you work with day-to-day more than the work itself?"

Notice that the recovery question is, itself, looking for an opinion.

Conversation, Not Q&A: Why It Matters

You have probably been told a hundred times to "have a conversation, not a Q&A." I was once in your shoes and never found a solid explanation of what actually separates the two. Here is a simple one, based entirely on talking time, measured past the small talk and the introduction exchange:

• Q&A | past the small talk and the introductions, they talk more than 80% of the time, you talk roughly 20%.
• Conversation | past that same point, talking time is split 60 to 70% them, 30 to 40% you.

Call it 80/20 versus 60/40. It sounds simple, and it is. The hard part is not measuring whether your chats are Q&As; it is actually having a conversation. If you want to come face-to-face with the problem, record the talking times on your next chat. I would wager many of you are running consistent 80/20 Q&As right now, and you won't fix it until you see it.

Here is the subtle trap. "Have a conversation" is not the same instruction as "talk more," because there is a limited amount you can actually talk about. Remember, we are measuring the part of the chat after the introductions, where they are answering your questions. If they talk about the deals they are on and you respond with your thoughts on Jerome Powell's latest speech, you might be splitting the microphone 50/50, but that is a conversation you do not want to have. You have to stay on-topic. Yet you also have very little control over what the topic is. Simply clarifying what you didn't understand implies sub-par knowledge of their job. Simply acknowledging their point and moving on implies you have no self-awareness, or that you are steering toward more familiar territory. Neither is ideal.

The way out of that trap is the construction method in the next section. It is also the real reason "complex" questions exist: they are how you earn a bigger share of the talking time without going off-topic.

How to Build a Question: From Simple to Complex

Instead of jumping straight into your next question, demonstrate that you understood their point first. If they talked for two minutes, aim to summarize their answer in less than 25% of that time, roughly 30 seconds, and then either relate it to a past experience of yours or raise the point you wanted to clarify. From there you launch into your next question, one that is related to what they said but still moves the conversation forward.

There are two flows any coffee-chat response can follow:

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

These two flows are really just two ways of taking a "simple" question and making it "complex." Picture a spectrum. On the left sit simple, non-targeted questions. On the right sit complex, targeted ones, built out with either a story from your past or a walkthrough of your thinking. The simple versions look like this:

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 is nothing wrong with the substance of those questions. The problem is that they hand the other person no boundaries and signal none of your own preparation. Now watch what happens when you upgrade them. There are two methods.

Method 1: Build a Statement

A Statement walks the other person through what you have read, heard, or expect, before you ask. It gives them the context for your thinking and a clear lane to answer in. Here is how I would ask those same three simple questions using a Statement:

"I've read that transitioning from an intern to a full-time analyst in investment banking can be quite daunting. The demands increase significantly, and the learning curve can be quite steep, especially when working on concurrent deals and on industries you may not have prior knowledge about. Given this, I'm curious about your personal experience. I've been re-doing the financial modeling courses I did throughout college for understanding now instead of completion – like back then (chuckle) – but would love to hear other suggestions you have for preparing for the job. Mainly though, when you transitioned to a full-time role, did you find that acclimating to the workload was the biggest challenge or was there something else that proved to be more difficult?"

"In my conversations with other bankers, I've heard a lot about the importance of team dynamics and culture. Some have mentioned how much they love their teams, while others aren't as enthusiastic about their coverage. As a student, I've found it hard to grasp the importance of culture within a team but can understand how much of an impact it'd have on one's day-to-day. I'm curious as I've heard mixed things about aiming for a specific coverage group given that it's hard to justify specializing in anything at this early of a stage in my career. With that in mind, how has your team been since you joined and, coming into the role, did you have a clear idea of where you wanted to end up? Any other details about your team would be greatly appreciated."

"I've heard that firm culture is often a deciding factor for many senior bankers choosing where to work, especially given the polarizing nature of what people consider "work-life balance". Some firms are work-hard, play-hard, while others, typically more top-heavy, prioritize free weekends but are very intense during the week. While it's hard for me to pick from the outside-in, as someone who's worked at 3 banks, one, are the culture differences felt at the analyst level, where we're really just executing as efficiently as we can, and two, what's the sort of culture that you prefer? I'm sure having experienced multiple different cultures you've at least found one you prefer more?"

Method 2: Craft a Story

A Story does the same work, but it leads with a real experience of your own. This is the flow my piano student used. Here is how those three simple questions look when they are built out as Stories:

"During my last summer internship at a boutique investment bank, the workload was initially quite overwhelming but very much in line with what I'd heard from my friends. Climbing up this learning curve was difficult, and I'm sure I have a long way to go, but by the end of it I'd gotten into a nice groove and had the chance to work on a few CIPs and comps tables. I can imagine it only gets more demanding from here, and my Associate was evidence of that. Talking to him, he said you just had to deal with it head on, and I largely agree. But, for you, in transitioning from a student to a full-timer, what were the biggest challenges you faced, and in particular, was there anything you had overlooked during your internship that you only realized the significance of when you returned?"

"Seeing how private equity investors think about businesses up close has been an amazing experience and the past 3 weeks at this job have been so enriching, particularly what I've learned about teamwork & culture. The emphasis they place on business' management teams was confusing to me at first, but seeing how well the people at this firm work together, a result of a huge effort to have weekly get-together's and after-work socials, it's sort of making sense to me that it'd be a hugely important factor in evaluating any private equity investment. With that said, I'm still interested in pursuing a career in Investment Banking out of school, for reasons I'd be happy to elaborate on, but wanted to know more about the team structure at your firm. Independent Advisors seem to run quite lean but, with an office the size of yours, I'm wondering if that's the case across all groups or, if not, what's unique about the groups that do?"

"What you said about your firm's culture was very interesting and reminds me of the firm I worked for last summer, where everyone seemed to be friends not just in the office but outside of it too. I even remember seeing my VP at the grocery store and, before I could turn away, he waved at me and came over – (chuckle) I felt so awkward…but it was very cool to see how much he cared. This was one of the firm's satellite offices, so it could make sense that the pace was relatively slower than their NYC office, for instance, but with where you guys are located it'd seem like deal flow would be very strong. I'm curious – how does the team over there, in spite of how busy work gets, maintain such a tightly-knit team? It really seems like you guys are in sync."

What it looks like live

The piano exchange from the opening is the Story flow in action: their answer, his 30-second summary, his own piano background, then his question. Now here is the same student a little later in that BofA chat, using the other flow. The Associate explains her team's structure:

"So then you're doing that, so you're an Analyst for a couple of years. As an Associate the responsibilities are shifted – obviously there's more of a leadership aspect as now you're managing analysts, but you're also managing above. On our team we have no VPs – we're 2 Associates, no VPs, and 1 Director. So the advice that's given to us, me and the other Associate, act like a VP and an Associate…here's your opportunity. We act like a VP as in we lead calls, we lead workstreams, we hold the pen on a lot of things – like on the deal that I'm on currently, I built the model, I build the customer analysis, and built the CIP – out of 80 pages, I built 60 pages. Basically, you take more ownership, you're leading – that's more of what you do. We had a weekly update call today and the Director was like 'You lead it, you know it best.' So you get more opportunities like this, though I would tell you that this is unique to our team and this dynamic is quite team-dependent. At the Associate level, at a baseline, it gets better in terms of face time with clients and leading those key workstreams. So yeah, that's how the role has developed so far"

"No yeah, thanks for the in-depth explanation. It was interesting hearing what it was like moving from an Intern to Analyst to Associate. I've kind of gotten a sense of what it's like to be an intern given I've worked for a year in Investment banking but also kind of as an Analyst but certainly not as an Associate. I also think it's really interesting how you mentioned your team was very flat and how there's no VPs and how that affords you the chance to get more learning experience than the typical Associate, almost like managing upwards and downwards even more than a VP. I was wondering how that came to be for the team, like was it always structured this way or? I'd imagine that it wasn't, that this wasn't the intended set up and that, with how crazy the market was as you mentioned, things got reshuffled and (chuckle) luckily enough they had 2 super competent Associates to step up to the plate and, like you said, fill the empty VP roles. I'd love to hear your thoughts, though, as this dynamic isn't something I saw working at that boutique."

Notice that here he actually asks the question before he finishes walking her through his thinking. That is fine. As long as you don't come across as incoherent and the other person can follow your question, the exact sequencing of what you say after your summary is of de minimis importance. Don't agonize over whether the question comes before or after your thought process.

In both exchanges, the student stretches his share of the talking time to that 30 to 40% conversation threshold, where most students would just acknowledge and move on. You don't need to say anything revolutionary to get there. You need to be polite, demonstrate your understanding, and ask a relevant question right after. The hard part is doing all of it at once: listening, forming your response, locating a past experience, and organizing your thoughts.

Prepare Five to Ten Questions, Expect to Ask One or Two

Here is a useful way to think about why preparation matters. Say you have only 10 units of mental processing power. During a chat, that capacity gets spent on two things: crafting a relevant question, or responding to their answer. If you dedicate all 10 units to crafting your next question, you have nothing left for responding, so you fall back on a bare "okay" and move on. That is a Q&A, and it is what happens in most coffee chats, not because students are careless but because the pressure is enormous and most simply haven't done enough reps to do both at once.

A prepared list of personalized questions removes the burden of forming questions on the spot, which frees up units for the intelligent responses that actually build rapport. Before every chat, I would aim to craft 5 to 10 personalized questions based on the person's background. Expect to ask only 1 or 2 of them. That is not a waste. The act of preparing sharpens your thinking, and the 1 or 2 you do ask can genuinely tip the scales. Type them up beforehand and keep them in front of you for the entire chat.

When the conversation drifts somewhere you didn't prepare for, the fix is to build a fresh question out of something they just told you:

"[their answer]…Got it, that makes a lot of sense. [summary of their points to demonstrate understanding]…you know, you mentioned earlier that you [played a ton of intramural volleyball in college], funnily enough I used to play too, was that just a college thing or are you still playing now? I'm sure it's difficult to find time for it and, when you do, there's probably a ton of other stuff you have to do too."

Personalizing questions is a skill, and like the skill of forming questions and responses simultaneously, you get faster at it with every chat you do.

The Two Jobs Your Questions Do

Once you can reliably build a complex question, the next layer is purpose. Every question you ask is doing one of two jobs.

Interview Ammunition

These questions exist to improve your own behavioral answers: the exact reasons, phrases, and context that great answers are built from. You obviously can't ask a professional an interview question the way an interviewer would ask you, so you use the Simple-to-Complex continuum to bridge the gap. The payoff is that professionals in a given role tend to give many of the same points when answering the most common behavioral questions, and these are people who broke in. Their answers are proven, and they are sharper now than when they were recruiting, because they have actually done the job.

Here are the transformations I would make to turn a behavioral question into something you can ask in a chat. They read shorter than the examples above because the summary and thought-process pieces are chat-dependent:

Rapport-building

• An analyst is usually happiest retracing their own recruiting story – how they navigated the exact process you're in right now.
• An associate tends to light up describing the first deal they truly owned a piece of, or whatever it was that earned them the promotion.
• A VP will often gladly walk you through the first deal where they were the one running point.
• A Director loves telling the story of the first big client relationship they brought in themselves.

Because rapport questions invite the other person to open up, they will sometimes carry the conversation somewhere you didn't plan to go. That is fine. Indulge them. They know what they are doing, and they are often going off-topic to make a point or share a lesson. Follow their direction, ask one or two genuinely interested follow-ups, and then steer back:

One soft signal worth tracking as you go: the length of their answers. The longer they talk, the more engaged they are. It is not a precise read on your odds, and you should treat it as something to experiment with rather than gospel, since you never know what kind of day they are having. But if their answers keep getting shorter, that is your cue to reassess what you are asking.

When You Ask Matters as Much as What You Ask

A brilliant question asked at the wrong moment is a wasted question. You know the saying about restaurants, "location, location, location," the idea that where a restaurant sits matters more than the food it serves. Coffee chats work the same way. Your most impressive, knowledge-revealing question is the food. Its location is simply when you ask it, and how related it is to what the other person just said. The quality of the question can only be fully realized if its placement is right. Expect to need 10 to 20 chats before you get this consistently right. A game is only fun once you have learned its rules, so pay down that ignorance debt quickly.

The good news is that you don't have to guess at the right sequence, because the other person hands it to you. The structure to follow is the same one they used when they introduced themselves. A full-time professional has refined their introduction down to the most salient points of their story, so it makes sense to circle back through those very points across the conversation. That is what maximizes rapport.

So listen closely to the implicit timeline in their introduction and note the important "chapters." Common ones include:

• Pre-college | typically a sport or activity they played at a high level.
• College | the finance catalyst, clubs, recruitment, internships.
• Post-college | full-time Analyst, "figuring it out," their current firm.
• Their 20s (for senior bankers) | switching careers, a notable professional accomplishment, moving country.

Use these chapters to bucket your questions. It makes the work of turning a simple question into a complex one easier, and it keeps you from "hopping around." When you ask questions of seemingly no relation to the last one, you make the other person feel unheard and build no rapport, and you come across as a disorganized candidate who is only paying attention to select parts of their answers. A structure that follows their chronology is so subtle they probably can't tell you are using one. What they can feel is the absence of confusion, and that clarity rubs off on how they perceive you.

To be clear, this is a dynamic structure, not a static one. It bends to who you are talking to and what they want to discuss. And it is not an agenda you announce. If anything would flatten your call into a Q&A faster than prefacing each question with "my next question," it is opening the call by telling a busy professional how you want them to spend it. Picture a high schooler asking how you got into your college, and then sending you a list of where to meet, when, what to wear, and the exact topics to cover. Prepared, sure. Also entitled, and lacking any self-awareness. Bring a plan, and use it as an outline you would never follow like a bible.

Two Questions That Make You Sound Arrogant

Beyond the Yes/No question, two specific question types reliably erode the rapport you have built. Both come from the same root: forgetting that the person you are talking to is ahead of you and knows their world better than you do. Be humble, and don't say anything that could be read as arrogant.

The first is the question asked in absolutes, a statement about a topic the other person knows more about than you, dressed up as a question:

"I saw you went from Investment Banking to Private Equity and I'm sure you were thinking of that from the very start, as most bankers do, and have been able to be a bit less of an Excel monkey since making the jump. Did you consider any Hedge Funds?"

The problem is that it leaves no room for an alternative, or it frames any alternative as abnormal. The tone is prescriptive rather than inquisitive. It says "you should have done this" instead of "you did this, here is why I think you did it, but I'd love to hear your perspective." Describe someone's own career back to them in absolutes and you sound like a know-it-all with no self-awareness.

The second is the show-off question, the convoluted one engineered to display your "knowledge," usually about a deal or the markets, and usually with no relation to what was just said:

"Given you're in the Energy group at Bank of Zimbabwe, what do you think of the recent spike in Crude Oil prices motivated by the regulatory changes recently enforced by the 5 major African oil producers – Nigeria, Angola, Libya, Algeria & Egypt – especially seeing as OPEC has expressed intentions to halt exports to the Western hemisphere after Bloomberg published that piece on the ever-worsening US-China trade war – have you seen that piece?"

That example is deliberately exaggerated, and I doubt any of you are showing off this egregiously. But you can probably see traces of it in the over-engineered questions you have asked, and trust me, the intent is obvious to the person on the other end. If you want to catch yourself, record your next chat and listen back. It may only be one or two questions. That is still enough to tip the scales toward a student who didn't sound arrogant.

The Close: The Three Questions to End Every Chat

There are three questions you should ask at the end of essentially every coffee chat, and the reason they don't read as presumptuous is entirely about placement. Aim to transition into them around the 20-minute mark, and at the very least make it to the 15-minute mark first. Here is the transition:

That confirmation matters. The other person has known this part was coming and has been assessing you since the start. By asking whether they have time before you ask anything "selfish," you remove any chance they read it as entitlement.

One more thing belongs here before the questions: an explicit expression of interest. It is implied by the fact that you reached out at all, but make it explicit:

The phrase "replicate that experience" is doing deliberate work. It is not as premature or forward as "join your team" or "work with you," but it still carries real weight and lands as honest and positive.

Now the three questions:

When you ask for a Teammate Connection, prepare in advance an idea of who you'd want to meet and why. You need a reason ready, because roughly 50% of the time they will respond with "What would you like to learn more about?" or "Who would be good for you to speak to?" Getting caught flat-footed there undoes the good work. Treat that follow-up as a neutral indicator, neither good nor bad.

Notice, too, that none of these three is a request for a referral. That is intentional. You should not be asking for a referral anyway, so there is no need to put them in the awkward position of saying no. It never hurts to ask the three questions, even if the chat went poorly, so ask them regardless of how the call has gone. If they avoid your questions or give curt answers across the board, your odds are probably already near zero, and the most productive thing you can do is reflect right after the chat on how you introduced yourself, responded, and crafted your questions. Alongside listening to your peers' chats or having someone review yours, that reflection is the single best way to find real improvements for next time.