Meeting someone over coffee is a staple activity of entrepreneurs. It's a cheap way to meet, it's neutral, and it helps sustain your addiction to the caffeine overlords that keep us all working 16 hours a day.

That all said, sometimes meeting someone for the first time at your local coffee shop can be awkward or less productive than you'd like. So let's explore the nuances of these frequent events.

Coffee meetings aren't blind dates.

Mitigate any moments of awkwardness that you can. This is a tiny detail, but buy your own coffee. Playing the “I'll pay, no I'll pay, no I'll pay" game is unnecessary. If we really want to dig into the psychology of it, this moment creates an unneeded show of power or desperation from one side. Get there a few minutes early and buy your coffee, then wait at the table while your new friend gets his (and hope both of you don't read this blog post).

Spend two minutes Googling each other.

Regardless of whether you're the one who initiated the meeting, you should spend some time getting to know the person you're having a conversation with. In other words, STALK. While it's great to have some background on someone when you talk to them, the more important part is that you bring a series of questions to the table. Nothing makes a conversation more grueling than one side not having questions for the other. If you're taking the time to physically meet with a person, then spend the few extra minutes to ensure you can get as much as possible from that discussion. Otherwise, just don't agree to it.

Don't have coffee out of obligation.

That leads me to the next and arguably most important point. As a good friend once told me,“Make sure that networking doesn't turn into not-working."Personally, I love having coffee with new people, and I do it every week. But I only accept these meetings if I can get something out of them as well. That might be something intangible like getting advice, or helping out a young person who's so damn smart they'll be my boss some day. But I'll never spend the time to meet with someone out of a feeling of obligation. This is obvious, but I'll state the obvious: If your heart isn't in this meeting, your brain won't be either.

Closing out the meeting.

This comes back to avoiding awkward situations. No one wants to be the asshole who says, “Hey...so I gotta go.” It can create an implication that you're too important to continue the conversation. It also can cut off the opportunity to take actionable next steps. First, it's polite to set expectations early on in the meeting. Let the person know when you need to leave. And if you want to get really fancy, set an alarm so you don't have to rudely check your phone during the conversation. Secondly, provide the person you're meeting with one or two actionable next steps YOU can take, even if they're as simple as,”I'm going to introduce you to so-and-so,"or, “Let me know when you hit the next big milestone and I'll provide you with feedback.” If you have zero interest in talking to this person again, provide him with constructive feedback (it sets the tone that you're going to be a tough customer) and ask him to follow up in a few weeks. You can always ignore at that juncture.


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