Calling All Conversationalists: You're in your coffee chat with an MD. How do leave an impression?

You're in a informal coffee chat with an MD, principal, etc. You've asked the usual questions (what got you into finance etc), and he's still neutral about you. To him you're still just some guy that wants to enter finance. You want to take the next step to make him really like you and that can only usually be achieved by talking about something outside of finance.

Two scenarios: a). You've identified a common interest, say sailing. How do you bring it up without it seeming random and forced and them knowing you've stalked their social media.

b). The guy's a total pariah. No social media. Nothing to go on except what he's told you in the last 30 minutes. How do you make him reveal his interests>

Look I totally get that so much of this occurs in free flow and there's no exact template. But not all of us are necessarily skilled conversationalists and need an occasional base to get started.

Appreciate your thoughts.

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