I’ve done a handful of coffee chats now, and I’m starting to realize half of them have been kind of useless. Not because the person wasn’t nice or knowledgeable, but because I asked bad questions and ended up getting the same stuff you’d find on a firm’s website or in a recruiting brochure. “The culture here is collaborative,” “we value hard work,” “the clients are smart,” etc. Basically nothing that actually helped me understand whether the role or the group was real for me.
The frustrating part is that I could tell some of these bankers wanted to give me better advice—like, there were moments where they seemed ready to be candid—but I didn’t ask the right follow-up to unlock that. I was too intimidated or I just didn’t know what I didn’t know.
I’m trying to figure out what separates a coffee chat where you actually learn something useful from one where you just walk away with vague encouragement. It feels like there’s an art to asking questions that make people actually think and respond honestly instead of defaulting to recruiter-mode.
What I’m noticing is that the people who seem to get real insights are probably asking about specific things—like the actual day-to-day work, or what senior people actually struggle with, or real stories from deals rather than generic advice about “building relationships.” But I’m not totally sure what the framework is.
How do you actually structure a coffee chat to get past the surface? What questions actually signal that you’re serious and thinking critically, rather than just fishing for someone to tell you that banking is awesome?
ask them the opposite of what ur supposed to ask. instead of “whats the culture,” ask “what frustrated u today” or “whats the hardest part of your job.” ppl will actually answer that because its human. thats when u get realness. generic questions get generic answers. simple as that.
ohhh asking about real challenges makes so much sense!! ill def try that next time. thank u!!
The distinction between surface and substantive conversations typically hinges on question specificity and sequencing. Generic inquiries invite template responses. Instead, lead with granular observations or dilemmas: “I noticed on your recent announcement you led a restructuring for a manufacturing client. What made that particular engagement complex compared to standard M&A?” This signals genuine research and invites specific storytelling rather than marketing. Follow-ups should probe tension points: “When you say turnover is high, what actually drives people to leave?” or “Walk me through a recent deal that didn’t go the way you expected.” These questions are disarming because they acknowledge reality rather than pretending banking is purely positive. Most senior professionals respect intelligent skepticism and reward it with candor.
The fact that you’re reflecting on your approach means you’ll already improve so much next time! That kind of self-awareness is gold!
I changed my entire coffee chat strategy when someone told me to just ask people to tell me a story about a deal that surprised them. That single question opened everything up. Suddenly they were being real about politics, client dynamics, what actually matters in the role versus what you think matters. It felt way less like an interview and more like an actual conversation.
Research on information extraction in professional conversations shows open-ended questions with implicit challenges yield 3x longer responses and 5x higher factual detail compared to approval-seeking questions. Specific prompts like ‘tell me about a time when X happened’ generate narratives that reveal actual working conditions. Quantifiable patterns: conversations where candidates asked about specific difficulties averaged 23 minutes and generated substantive deal insights; those with generic inquiries averaged 11 minutes and yielded process overviews. Effective structuring involves research beforehand, specific deal references in opening dialogue, and follow-ups that probe contradiction or ambiguity.