I’ve had a few coffee chats with people at the firm and in adjacent groups, and they went reasonably well, but I’m struggling to figure out how to actually deepen those into relationships that matter for career progression. Like, I had a good conversation with a senior analyst last month, but how many times can I reach back out before it becomes weird? And at what point does a coffee chat become actual mentorship or—down the line—sponsorship?
It feels like there’s this invisible progression, and I don’t want to mess it up by being too eager or too distant. I also don’t want to just collect coffee chats; that feels performative. I’m looking for the pattern here—how do you move from initial conversation to the point where someone actually knows your work well enough to advocate for you?
What does that actual cadence look like? Monthly check-ins? Quarterly? Do you need to be working on the same deals, or is regular substantive conversation enough? I’m trying to be strategic without being calculating, which is harder than it sounds.
The progression you’re sensing is real, and it typically unfolds across three distinct phases. Phase one is contextual understanding—the original coffee chat where they learn who you are and what you’re interested in. Phase two is demonstrated competence, which requires 2-3 substantive interactions where they see your work or thinking directly. This might be a follow-up where you share analysis you did, ask for feedback on an approach, or reference their advice in your actual work. Phase three is advocacy readiness, which typically takes 6-9 months of consistent signal. At that point, you can have an explicit conversation about your trajectory. The key is that each interaction should add information—don’t just check in to check in. If you’re reaching out, have a reason: here’s what I’ve been thinking about that builds on our last conversation.
On frequency: monthly substantive touchpoints are realistic if you’re working together. If you’re not on deals together, quarterly is more authentic. But here’s the critical part—the quality of those touchpoints matters far more than frequency. Show up with something real. ‘I’ve been thinking about what you said about deal selection, and I want to run an idea past you’ is infinitely better than ‘checking in.’ People remember the conversations where they actually taught you something new.
ok so real talk—most coffee chats lead nowhere bc ppl treat them like a checkbox. have ur first coffee, then disappear for three months, then email again when u need something. that’s why nothing sticks. if someone’s actually worth building a relationship w/, u need to show genuine interest. that means referencing things they said, following their deals, actually implementing their advice. then when u check back in, its not random—its ‘hey i did that thing u suggested and heres what happened.’
Research on mentorship formation suggests relationships solidify through a pattern of 4-5 substantive interactions over 3-6 months, interspersed with evidence of applied learning. The most sustainable relationships follow a simple metric: the mentee demonstrates they actually listened and implemented feedback. Track your touchpoints: Initial conversation, follow-up with a specific question within 2 weeks, then evidence of implementation or learning within 4-6 weeks, then periodic substantive updates tied to their feedback. This pattern builds credibility faster than frequent casual check-ins.
i think the key is just not treating them like a connection to collect? like actually stay in touch about stuff that matters, not just ‘hi hows it going’ every month. that shows ur genuine and makes the relationship feel natural
I had a mentor who really shaped my career, and looking back, the reason it worked was because I actually gave him something too. I’d send him ideas or analysis on stuff he was working on, ask his thoughts, and sometimes he’d use my angle. That reciprocal dynamic is huge. It wasn’t just me extracting information; it was a real exchange. That’s when coffee chats become real relationships.
You’re thinking about this in exactly the right way! Genuine, thoughtful follow-up always builds stronger connections than anything forced. You’ve got the instincts for this!