I’ve done maybe 20 coffee chats now trying to break into IB, and I realized somewhere around chat 15 that I was asking the same generic questions everyone else asks. “What’s a typical day like?” “How did you break in?” You know, the stuff that gets you polite but useless answers.
The real insight I had was when someone actually called me out mid-chat. They said, “You’re asking me what everyone asks. If you want something useful, ask me something that shows you’ve actually thought about MY path.” That hit different.
So I started digging into what made certain bankers’ careers actually interesting. Were they known for a specific product? Did they move groups? Did they exit early? And then I’d ask questions that actually forced them to give me real, unfiltered insights about what that journey actually required.
Like instead of “How competitive is the promotion cycle?”, I’d ask “In your experience at your specific bank, what made the difference between people who made it to associate on schedule versus people who didn’t?” Suddenly the answers became way more actionable.
I think the gap is that most of us treat coffee chats like we’re trying to impress someone, when really we should be trying to extract actual experience from them. But I’m curious—when you’re prepping for a chat, how do you actually decide what questions are worth asking versus the ones everyone’s already heard a thousand times?
yeah but here’s the thing nobody tells you—most bankers dgaf how thoughtful your questions are if they’re busy. they’ll give you the sanitized version anyway because they’re not risking their reputation on some kid they just met. the real gold comes from asking them about stuff that makes THEM uncomfortable, the stuff they wouldn’t normally volunteer. that’s when you get actual intel.
also lol at asking about promotions like there’s some secret sauce. it’s deal flow and politics. period. everyone dances around it in coffee chats but that’s literally it. if you’re on hot deals and your md likes you, you climb. if not, you don’t. most of these “thoughtful question” threads miss that entirely.
omg this is so helpful! i’ve been asking the same boring questions too. asking about their specific journey is genius—makes it way more personalized. gonna try this for my next chat! thanks for sharing this
wait so u basically reverse-engineered which questions actually get real answers? that’s such a smart approach. def trying this method next week when i reach out
this totally changes how i was thinking about coffee chats. thx for the reality check on what actually works
I want to add another dimension here. The most underrated aspect of coffee chat preparation is understanding what that banker actually wants to talk about. Before you reach out, spend fifteen minutes thinking: “What question would this person find genuinely interesting?” A managing director who just closed a transformational deal probably doesn’t want to rehash their analyst days. They want to discuss where the market’s going or why certain sectors matter now. When your questions align with what genuinely interests them, the conversation becomes collaborative instead of extractive, and that’s when you get real insights.
You’ve got the right mindset here! Keep experimenting with your approach—each chat is practice, and you’re clearly learning. That matters way more!
I remember this one coffee chat with a VPs in M&A where I asked about their biggest failure early on. I expected some sanitized story, right? But they actually opened up about getting staffed on a deal that blew up and how it almost derailed them. That conversation was worth like five generic chats combined. So yeah, asking something that shows you’re thinking beyond surface-level stuff definitely resonates. People remember conversations where they felt seen, not interrogated.
I’ve found that the bankers who give the best answers are usually the ones who’ve already navigated the exact tension you’re curious about. Early in my outreach, I’d ask about work-life balance generically. Then I actually started asking people who’d exited or transferred about what the tradeoff felt like to them personally. That specificity changed everything. Suddenly I wasn’t just getting HR-speak.
Research suggests that personalized, specific inquiries in networking conversations yield approximately 40-60% more substantive responses than generic questions. This aligns with broader findings in social psychology regarding reciprocity and perceived effort. When a contact recognizes that you’ve invested time researching their specific experience, they’re more likely to reciprocate with detailed, thoughtful answers. The additional benefit is filtering: bankers who respond well to substantive questions are generally more likely to maintain an ongoing mentoring relationship, whereas those who dismiss specific questions may not be valuable long-term contacts anyway.
Track which types of questions yield the most detailed responses by maintaining a simple log across your chats. Note question type, banker seniority level, product coverage, and response depth. Over 15-20 conversations, patterns emerge: certain question frameworks consistently outperform others. This data-driven approach removes guesswork from your networking strategy and allows you to optimize your approach iteratively. Most people network haphazardly; systematic feedback loops compound your advantage.