I’ve been on the receiving end of a lot of advice about building relationships, and one piece keeps coming up: ‘Just ask people for advice.’ It always feels vague to me, though. Like, ask them what? Ask how? And how does asking for advice actually transform into a meaningful relationship or advocacy for associate?
I tried this a few times. I reached out to a director from another group and asked, ‘Hey, I’m thinking about my career path. Do you have time for a quick coffee to get your thoughts?’ He said yes. We met, I asked him general questions about the industry and what made good investment bankers. It was nice, but it felt like… I’m not sure what it was. Friendly? Generic? Productive?
Then I had another coffee where I asked a VP about a specific situation I was navigating on a deal—like, actual tactical stuff from my day-to-day. That conversation felt completely different. Shorter, more focused, he actually seemed engaged.
I’m wondering if there’s a skill I’m missing around how to ask for advice in a way that’s specific enough to be valuable but not so specific that I’m asking someone to do my job. What’s the advice that actually moves the needle, versus the advice that’s just ‘nice to have coffee’ territory?
There’s a crucial distinction between generic advice-seeking and valuable specificity. Generic: ‘What makes a good banker?’ Valuable: ‘I’m on this leveraged buyout and I’m trying to understand how to model terminal value scenarios for a cyclical business. What’s your instinct on this type of situation?’ The second approach shows you’re thoughtful,engaged with real problems, and seeking genuine insight rather than vague mentorship. Senior bankers respond to specificity because it signals seriousness and creates genuine dialogue rather than a transactional coffee chat.
The most effective advisor-seeking follows a pattern: identify a specific challenge, document your thinking on it, and ask for feedback on your approach rather than asking them to solve it. This positions you as someone who thinks, rather than someone who just wants answers. It also gives the advisor something substantive to contribute, which makes the interaction memorable for them. People remember the analysts who asked smart questions, not the ones who asked generic ones.
lol ppl say ask for advice but what they really mean is be interesting enough that they want to help u. generic coffee chat? theyll forget u in a week. but ask someone about something theyre actually passionate about or something where u seem genuinely thoughtful? now ur memorable. its not the asking, its being smart enough to ask something worth answering.
ooh so specificity is the key. got it. makes sense that someone would engage more with real problems vs generic career questions thx
I remember asking a VP about how he thought about client risk assessment, and it totally changed how we interacted. Before that, coffees felt like interviews. After that question, it felt like actual conversation. He started emailing me articles, asking me about deals I was on. The difference was that I asked something that made him think, not just ask him to deliver wisdom. That relationship actually went somewhere.
You’re developing great instincts about this! Ask specific, thoughtful questions when you can. Show genuine curiosity. People love helping analysts who are actually engaged. You’re on the right track!
Studies on mentorship effectiveness show that advice-seeking conversations are significantly more likely to convert to ongoing relationships when the advice-seeker demonstrates prior preparation and asks questions that require genuine expertise to answer. Vague questions yield vague responses and low follow-up rates. Specific questions—particularly those that reveal your thinking—yield substantive dialogue and higher likelihood of repeated interaction. The metric is whether the senior person wants to know how your situation evolved, not whether the coffee was pleasant.