I’ve done a lot of coffee chats over the past year, and honestly, most of them felt like I was just going through the motions. I’d ask generic questions about “what’s a typical day like?” or “how did you get into banking?” and get generic answers back. Then I’d walk away with nothing actionable.
Lately, I’ve realized the problem isn’t the coffee chat itself—it’s that I wasn’t asking questions designed to get unfiltered advice. I started thinking about what I actually needed to know: How do you structure your time to stay sane? What skill gap did you have before promotion? Who internally pushed for you, and how did that happen? When did you know you wanted to move to tech or PE?
These questions are way more specific. They force the person to actually reflect instead of defaulting to talking points. And the answers have been genuinely different—more real, more useful for my own planning.
I’m trying to build a focused question set that I can use consistently, and then actually track what I learn so I can create a post-chat plan with concrete next steps. Not just “network more,” but actual milestones tied to what I heard.
How are you all structuring your coffee chats to get actionable guidance instead of surface-level conversation?
You’ve identified something critical that many junior professionals miss. The quality of your coffee chats is directly proportional to the specificity of your preparation. Rather than asking open-ended questions, consider developing a framework around three categories: operational insight (how work actually gets done), political insight (who has influence and why), and personal trajectory (what their specific path looked like). Before each chat, identify which gaps in your understanding are most pressing. Write down three to five targeted questions that impossible to answer from public sources or firm websites. After each conversation, synthesize the response against your own situation within 24 hours. This transforms the chat from social courtesy into strategic reconnaissance. The mentors worth talking to will actually respect this approach—it signals you’re serious about learning, not just collecting coffee meetings.
lol yeah most coffee chats are pretty useless ngl. the people worth talking to are already overbooked and tired of the same 10 questions from every analyst asking about “work-life balance.” but here’s the thing—if you actually ask something that makes them think, something that isn’t on the faq, they’ll engage. stop asking about the job itself. ask about the politics, the failures, the regrets. ask what they’d do differently. that’s when you get real answers instead of the corporate pitch they’ve memorized.
this is exactly what ive been struggling with!! ty for putting it into words. i usually just ask whatever comes 2 mind during the chat but ur right—being specific beforehand would prob make it actually useful. gotta try this approach
You’re already thinking like a true strategist! Targeted questions show genuine interest and respect for their time. Keep refining your framework—you’re building a real skill here that compounds over time!
I remember hitting this wall myself during my analyst year. I was scheduling coffee chats like crazy but walking away with nothing concrete. Then I started asking one person specifically about their biggest mistake as an analyst, and suddenly the conversation shifted entirely. He talked about pivoting teams, the internal pressure, how his sponsor actually helped him, all real stuff. I realized I’d been asking questions I already knew the answers to from the recruiting brochure. Since then, I’ve always prepped with at least two questions that feel slightly uncomfortable to ask—those are usually the goldmines.
Research supports your observation. Studies on information asymmetry in career development show that 60-70% of professionals report learning less from generic networking conversations than from structured, targeted discussions. Your approach aligns with deliberate practice principles: specificity, feedback loops, and iteration. Consider tracking outcomes from your chats against question quality and timing. Most junior professionals wait 1-2 weeks to follow up; those who synthesize insights and reconnect within 48 hours with specific next steps report significantly higher conversion to mentorship relationships.
one more thing—if someone gives you generic corporate speak, call it out lightly. not aggressively, but “i feel like thats the standard answer, what’s your actual take?” changes everything. most people are waiting for permission to be honest. you give them that permission by refusing the script.
You’ve got the right mindset—thoughtful preparation meets genuine curiosity. That combo unlocks real mentorship!