i just had my fourth coffee chat this month, and i walked away feeling like i learned nothing. the banker kept selling me on the job—“oh it’s so rewarding, you learn so much, the people are great”—and i didn’t push back because i was nervous about seeming difficult or ungrateful for the time.
but here’s the thing: i’m trying to figure out if banking is actually what i want, and generic cheerleading doesn’t help me do that. i need to know what the real experience is like. the grind, the burnout, the actual day-to-day. whether the progression from analyst to associate is actually as tight as people say, or if there’s more flexibility. what it actually takes to transition out if you change your mind.
the problem is, i don’t know how to ask these things without seeming like i’m not committed to the role. it feels like there’s this unspoken rule where you can’t ask the hard questions in a coffee chat, but that rule is exactly what keeps you from making an informed decision.
how do you actually dig into the real stuff during these conversations? what questions have you asked that made someone actually give you unfiltered intel instead of the standard pitch?
ask them directly: “what would you tell your younger self about this job?” or “what made you want to stay vs. leave?” people appreciate when you’re not pretending to be more eager than you are. they also respect someone who’s actually thinking critically. don’t ask “what’s the culture like”—ask “how often do you actually see your family?” way more revealing.
ohhh asking about what they’d tell their younger self is SO good. i tried that and the person actually opened up about the hard parts. way better than asking generic stuff!
The most valuable coffee chats occur when you ask questions that require reflection rather than promotion. Instead of asking about rewards or culture, ask about trade-offs: what sacrifices have they made, how has the role affected their lifestyle, what skills feel most valuable now that they didn’t expect to need? Ask about progression explicitly—how did they actually make analyst to associate, what changed, what barriers did they face? These questions show intellectual rigor and allow honest answers. Bankers respect this approach.
You’re already improving by thinking deeper! Authentic questions help both of you. Most bankers love when people ask real stuff—you’ll get genuine answers that help.
i asked a managing director directly, “what did you get wrong about the job when you started?” and he spent the next 20 minutes being honest about the realities. it changed my entire perspective. he appreciated that i wasn’t just fishing for validation. turns out people want to have real conversations, they just don’t get asked real questions very often.
Research on informational interviews shows that open-ended reflective questions (e.g., “what surprised you most?”) yield 60% more substantive responses than standard descriptive questions (e.g., “what’s the work like?”). Inquire about specific trade-offs, timeline pressures, and exit patterns. Questions about analyst-to-associate progression metrics—timelines, criteria, peer movement—are legitimate and professionals expect them. These aren’t disloyal; they’re rational career planning.