The Unspoken Rules of Startup Coffee Meetings

If you are in the process of raising funding for your startup — you better like coffee.

Well, you don’t actually have to like coffee, but you do have to be very open to spending time at cafe’s as you meet throngs of potential contacts, friends-of-friends, and if you’re lucky… investors.

Over the past ten years, I’ve certainly issued my fair share of coffee meeting invitations — especially when I was in the process of launching eFuneral.  Since then, I’ve found myself on the other end of those invitations.  In fact, I was invited to coffee this morning — and I would say that the person I met with had good “Coffee Meeting Etiquette.”  I’ve certainly been a part of other coffee meetings, though, where that wasn’t the case.

For those that are just getting started on their java-filled coffee meeting journeys, I thought I’d detail what good coffee meeting etiquette actually is.  But before we get into it, let’s start with some good news:

If your coffee meetings are startup-related — perhaps with the aim of getting to know investors or simply getting feedback on your business — and you’re located in an up-and-coming startup community as opposed to a very established one, you don’t have to worry much about rejection.

Whereas investors in places like Silicon Valley will tell you to not ask them for coffee — those in more nascent startup communities are more likely to accept your offer.  They want to help their startup community, and taking the time to meet for coffee isn’t a huge ask of them.  Granted, they can’t do this all of the time — and maybe there are times where their schedule simply doesn’t permit (especially if they’re the type of person that’s asked quite often).  But in my 10 years in Cleveland’s startup community, I’ve only been turned down once or twice when I’ve asked others to meet.  It’s therefore the case that when I’m asked, I generally try to make it work.  It’s hard — and it may not happen for several weeks.  But it’s my way of helping somebody that was in my shoes just a few years ago.

Of course, there is proper etiquette for coffee meetings — and it’s important to follow this etiquette in order to improve your chances of your invitation getting accepted and to keep a good relationship going with the person you meet.

1.  Don’t let your invitation be the first time they’ve seen your name.

Coffee meetings are really just networking — and I believe dating is an analog to networking.  If somebody just called you up out of the blue and asked you out on a date — and you’ve never met this person and don’t even know who they are — would you accept?  Of course not.  It doesn’t matter how they described themselves (well, okay — for some of you this would matter) or what their common interests were, it would just be weird to accept that offer.  The same goes for coffee meetings.  Do whatever you can to make sure that the person actually is familiar with you before reaching out.  This could be a mutual introduction between a common friend.  It could even be that you’ve interacted with the person before on Twitter or LinkedIn.  Whatever the case may be, make sure there is some sort of connection before reaching out.

2.  Do your homework.

Why do you think this person would be interested in meeting with you?  Is this an investor who has invested in other companies similar to yours?  Is this a User Experience expert who might be interested in talking shop about your work in User Experience?  Learn more about the person ahead of time, and let them know that you’ve done your homework.  You could say something like:   “I’ve read some of your blog posts on why user experience matters so much when designing a website — and I’d like to get your input on whether we’re doing a good job with that aspect of our launch, as we’ve been trying to take that to heart.”  This shows the person on the other end that you know about their background, and there’s a specific reason about why you’d like to meet them.

3.  Go where they are.

Do you live on one end of town — but they live on the other end?  Don’t offer to meet halfway.  If you’re asking them to coffee, you should offer to meet them at their favorite place near their home or office.  They are taking the time out of their schedule to meet with you for your benefit.  The least you can do is to lessen the inconvenience you’re causing by meeting at their location of choice.

4.  Offer to buy.

When I accept an invitation to meet for coffee, I don’t expect that the other person will buy my coffee.  It’s nice if they offer, and I may accept the offer.  However, some others may expect this.  So it’s always safe to pony up the three or four dollars their nonfat mocha will cost you.  Consider it a very low-cost, high-value investment you’re making in yourself.

5.  Address time up front — and stick to it.

It’s easy to let time get away from you when you’re excited and having a great conversation.  Don’t.  Ask them up front (either by email leading up to your coffee or right at the beginning of the meeting) how much time they have available.  If it’s 30 minutes, realize that you’re going to need to stick to that 30 minutes.  Don’t assume that they’ll tell you when they don’t have any more time.  Some people will be very up front with you after that 30 minutes has passed.  Others may not — but they’ll hold it against you if you ended up taking twice the amount of time.  So when there are only a few minutes left, let them know that you’re conscious of their time and know that you should wrap up — and begin to make your final asks.  If things are going really well, perhaps the other person will suggest that they actually do have more time.  That’s great — but don’t assume that this is the case.  If they offered to give you 30 minutes, then that’s the time you have.

6.  Listen for 2 or 3 (or more) minutes for every minute you talk.

You only have a limited time with this person.  Don’t waste that precious time by spending the majority of the meeting going on and on about your life story.  If you’re really there for feedback, get that feedback.  Be concise with them to set the stage for why you wanted their feedback and explain the situation to them — but let them talk.  And listen.  Don’t try to look impressive by adding onto their insights with “smart” insights of your own.

7.  Take notes.

I don’t care if you have a photographic memory.  You should be taking notes at this meeting.  It just shows that you really value what the other person has to say.  You don’t have to take notes the entire time — but make sure you note really interesting/valuable insights you’re gaining.

8.  Offer to help them.

If you’ve asked somebody to meet for coffee and they’ve accepted, it’s probably the case that you’ve gained a lot of value out of the meeting.  They’ve answered your questions, they’ve suggested other contacts for you to meet — you’re the one that’s gained.  Yes, they may have received a cup of coffee out of it, but let’s face it — is a cup of coffee really worth 30-60 minutes of their time?  So offer to return the favor. Is this investor looking for more dealflow?  Is this software developer looking for new clients?  Is this marketing pro looking to connect with others in their industry?  Try to understand how you can be helpful to the other person and offer to help them.

9.  Follow-up.

You should always thank somebody that has taken the time to meet with you.  But go beyond a simple “Thank You” email.  Let them know just how valuable the meeting was to you.  Did they suggest a specific book for you to read or podcast to listen to?  Take the time to read (or at least, start) the book and listen to that podcast — and let the person know what you like about it so far.  Did they suggest somebody that you should meet with.  Take the initiative to reach out to that person — and let your coffee meeting guest know that you have a meeting lined up.  People take coffee meetings because they genuinely want to help.  If they can actually see that you’ve taken their advice and are doing something with it — it will help them feel like the time they spent was valuable.

Coffee meetings can be grueling, but they can be very satisfying (for both ends) if done right.  And who knows — perhaps that one cup of coffee is the beginning of a long and close relationship.  Just make sure that you follow the rules.

Are there rules that I’m missing?  Do you have any crazy coffee meeting experiences to share?  Feel free to get the conversation going in the comments section below!

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  • Chang Chin Hing

    Very true. Been practicing this a lot, although I have made my fair share of mistakes in the past. Love the blog design 🙂

    • Thanks! Hey, I wrote the article and even *I’ve* made mistakes. 🙂

      And thanks for the compliment about the blog. Eighties WordPress theme FTW….

  • Its a real dance. As an investor/ mentor I am looking to listen more than I speak as well. Hopefully both parties talk enough for a good conversation!

  • freedumb123

    What do you think of bringing a printed piece of paper that has a list of questions at the top and a section for notes at the bottom to your coffee meet ups? I like to do that to add structure to the meeting. I don’t use it as a crux, but as a way to make sure I ask all or most of the questions I wanted answered if I forget.

    Does it look too eager or maybe robotic to do this? Let me know, I’m looking for feedback.

    • I don’t have a problem with this at all! Everybody organizes differently (whether with handwritten notes in a notebook or a printed piece of paper). The important thing is that you’re prepared for the coffee meeting… and the more prepared you are, the more you’ll get out of it (and the more you’ll respect their time). So I say go for it!

      • freedumb123

        Thanks, Mike. It’s good to get your input; now, I can do it with confidence!