5 Ways to Spice Up a Coffee Meeting

I’m on the heels of a whirlwind trip to San Francisco for work where, in addition to hosting 4 USV Network events, I had 8 different coffee meetings all over the city.

It can sometimes feel like a drag to do so much running around, but luckily for me, I got the chance to connect with some real pros. And along the way, I learned a few good tricks about how to spice up the traditional “let’s grab a coffee.” In the spirit of openness and transparency, I thought I’d share.

Coffee Tip #1: Go for a walk

This is perhaps the best way to spice up a coffee meeting. Take your coffee to go. Of course, this is easier in warm weather climates, like San Francisco, where I just visited. But even in NYC, as long as you’re bundled up in a hat and scarf, a walking meeting through a park can be the best way to get to know someone while engaging in a passive activity. My favorite walking meeting of the trip took place (as so many do) on South Park in SoMa.

Coffee Tip #2: Sit on their side of the table

This one threw me off-guard initially this week, until I realized that it was the ideal way to instill a feeling of collaboration immediately. I’d arrived first at The Wing and popped into the cafe area for a latte to catch up on emails. When my meeting date arrived, she slid over to my side of the table, suggesting that we look together on my laptop on some of the materials that I’d sent over. Like the walking meeting, this tactic proved to be a great feeling of mutual exploration and less focus on making constant eye contact with a new person.

Coffee Tip #3: Be brutally honest

On another meeting this week, I kicked off as I so regularly do: “How are you doing?” But the response stood out immediately: “Honestly, not that great.” It’s so rare to have a new acquaintance open up with that much honesty, and as a result, it disarmed me and really set the tone for the rest of our conversation. In the end, we both agreed we were feeling a little bit better 45 minutes later, when we each jetted off to our next meetings of the day.

Coffee Tip #4: Take them on a tour

I’m a huge fan of “the office tour.” It doesn’t even matter what your office looks like or how big it is — there’s always something interesting to show. And you can learn a lot about a person pretty quickly by noticing what things they point out to you in the environment they sit in every day. Sadly, tours never happens as often as I like, so it’s always a treat when they do. This week, I was lucky enough to get a tour of Airbnb’s HQ office in San Francisco — complete with a peek at a couple of their famous conference rooms, modeled off of actual listings. This one felt particularly fun for me because if you ever visit me at USV, I’ve probably shown you another “famous” artifact from our cultural lore — a box of Obama-O’s right in our front conference room.

Coffee Tip #5: Invite them to your next meeting

And last but least (but truly the most lovely surprise of them all) was the woman who, after an hour-long coffee date at Blue Bottle, invited me to tag along with her on her next meeting. “I’m so sorry, I have to run,” she said. “But I really think you’d hit it off with the person I’m meeting next. Would you like to join me?” Unfortunately, the timing didn’t work out for me, but I so loved the idea of inviting a “tagalong” to another meeting, particularly when connecting with more junior people. Related: I’ve had meetings in NYC with a couple of folks who bring a “shadow” with them. This, of course, is the best way to learn.

So there you have it. Five tips from five great meetings this week. I know I’ll be carrying a couple of these with me, and I hope they resonate with you too. Happy meeting, everyone!

Originally published at Dry Erase.

GM @USV, alum of @StackOverflow and @NorthwesternU, board member at @CompSci_High and @NUalumni, co-founder of #BeyondCodingNYC

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