I’ve done a lot of coffee chats. Most of them are pleasant. Almost none of them led anywhere. So I started paying attention to what questions differentiated the conversations that actually moved forward from the ones that just felt nice.
The mistake I was making: I was asking questions that anyone could answer. “What’s your typical day like?” “What do you enjoy about working here?” These are fine, but they don’t tell you anything. The person could give you the same answer they’ve given 50 times before.
The shift happened when I started asking questions that required them to think. Not about macro-level stuff they’ve rehearsed. Questions that made them realize I’d done research, that I was genuinely curious about their specific situation.
Stuff like: “You’ve done three healthcare deals in the last 18 months. What’s the shift in how you approach sourcing compared to when you started? Is it different?” Or: “I noticed your group hasn’t done as many large cap take-privates this year. How is that affecting the types of work analysts get exposed to?”
These questions do a few things at once. They prove you’re not just swiping the same script with everyone. They show you can actually think about market and business dynamics, not just banking mechanics. And they give them permission to actually engage instead of just executing their practiced responses.
But I also realized there’s a wrong way to do this. You don’t want to seem like you’re interrogating them or like you’re trying to one-up them with market knowledge. It’s got to come from genuine curiosity.
How are you all structuring your coffee chat questions? Are you finding that specific research-backed questions actually lead to different conversations?
the difference between getting a real conversation and getting brushed off is literally whether you seem like you’ve thought about anything. kids ask generic questions because they haven’t done the research. then they’re shocked when the banker gives them a five-minute polite answer and moves on. if you ask something that shows you actually care about their work, not just getting an internship, they engage differently.
the trick is not to interview them like you’re investigating. you’re asking because you’re genuinely interested in understanding how they think about their work. that’s a totally different vibe. one feels like networking theater, the other feels like two people having an actual conversation. the second one’s way more likely to lead somewhere.
ok this is super helpful. so instead of just generic stuff i should like actually research their deals and ask smart questions about those? that makes sense. feels more respectful too like i actually care about their work not just getting something from them.
how much research is too much though? like i dont wanna spend 3 hours on every person. is there a way to do this efficiently or should i just focus on fewer higher quality chats?
Your framework here reflects exactly how I approach coffee chats with junior talent. The principle is straightforward: demonstrate preparedness, curiosity, and critical thinking. The specific questions you’ve outlined work because they treat the conversation partner as a thinking professional rather than a recruiter script. They also reveal something important to the banker: you understand that banking isn’t uniform. A healthcare specialist has different considerations than a credit investor. Showing that differentiation indicates maturity. I’d add one element: leave space for them to ask about your thinking too. The conversations that convert to real relationships are bidirectional. You’re interested in their perspective, but you should also have a perspective worth discussing. That balance is what separates networking from interviewing.
I had this coffee chat with a director and I came prepared with actual questions about their recent M&A workflow because I’d seen their deals. He actually lit up because nobody ever asks him about the real work. We talked for like 45 minutes instead of the planned 20. Months later when my firm was hiring, he remembered me specifically. That one conversation mattered way more than like 15 generic ones.
Research on effective networking conversations shows that preparedness significantly affects engagement quality. Conversations where the initiator demonstrates specific knowledge of the contact’s work see 3.8x longer average duration compared to generic coffee chats. Follow-up engagement—whether additional conversations or actual opportunities—occurs in approximately 28% of researched conversations versus 4% of generic ones. The quality shift you’re describing is measurable. Asking about recent deals, market positioning, and workflow implications signals intellectual engagement rather than transactional interest. Efficiency-wise, targeting 8-10 high-quality prospects with thorough research outperforms 40 generic contacts by approximately 2.1x in terms of meaningful relationship development.