Tag Archives: Mentorship

The Art of the Coffee (Meeting)

The Art of the Coffee Meeting

9 Tips for mentees, mentors, and yentas

As a genetically pre-disposed yenta, over the last decade I’ve managed to find myself work that enables me to do what I love: be a matchmaker and a coach. The great news is I’m far from alone; our community has a powerful peer-to-peer mentorship movement afoot.

Kyle Kesterson, who is, in fact, a Freak'n Genius.

Kyle Kesterson, who is, in fact, a Freak’n Genius.

Luminaries in the startup community, including Marcelo Calbucci and Kyle Kesterson, hold regular entrepreneur office hours. Seeking mentorship can be a great forcing function– you’ll have to crystallize your thinking on what you and your business need. Providing mentorship is a great way to stay on top of your A-game–there’s no better way to truly understand a topic than to have to explain it. As a community we can help each other with introductions (matchmaking) and learn from each other’s mistakes (coaching). So how do you unleash the power of the mentor network if you’re just getting started? Here are some first-date tips:

For “Mentees”:

  • Ask for advice, not help. Everyone likes to feel like an expert. Not to mention, desperation is a stinky cologne (thank you, Super Troopers). Listen well, but don’t forget, it’s your company (thank you, Techstars). That means seeking advice is a poll, not a vote: the decisions are on you.
  • Make it easy to say yes. Put guardrails around the request: “I’d like to meet for 30 minutes to get feedback on my investor pitch deck.” That meeting has a good plot: a well-defined beginning, middle, and end.
  • Respect the network. Remember whoever introduced you to this new connection is putting their reputation on the line for you. Therefore:
    • don’t embarrass them: I’m not talking about chewing with your mouth open– though maybe don’t do that either– but do show up prepared and ready to take notes.luke and yoda
    • close the loop and let them know if the intro was helpful; they’ll be more likely to do it again. From where I’m sitting, Joey Kotkins of Inside Social (Techstars class of 2013) has achieved jedi master status in this arena: timely, brief, informative follow-up. Part art, part science, but at the end of the day, all discipline.

For Mentors:

  • Respect the request. Just because someone asks you for advice, if she doesn’t take it, it doesn’t mean she’s a bad “mentee,”  or even a bad listener. She can consider your opinion without agreeing. Better yet, to avoid this trap, try not telling entrepreneurs what to do, but instead ask them probing questions. Comparing notes with investor and mentor Kim Rachmeler, she’s fine-tuned the Socratic method for startups, an approach that truly enables entrepreneurs to own their destinies.
  • Protect your network. If my mental rolodex is doing my bidding and we’ve had a good meeting, before I finish that non-fat latte, I’ll try to mention a few comparable companies or potentially helpful connections. Instead of rushing home to do those intro’s, however, I really do want to know if they’re the right resources, and will ask you to circle back and let me know if they are.  And yes, it’s a test. If you don’t take the time to check them out, it doesn’t bode well for how you’ll treat those connections in the future.
  • Beware calendar creep. Carve out a set time, every week or every month, whatever the frequency, so it doesn’t take over your calendar. Don’t nickel-and-dime yourself with the commute time to and from meetings, so pick a place, stay put, and pack as many meetings as you can into your allotted time.  These days, mine is Thursday afternoons at Ada’s Technical Books and Cafe.

Everyone can be the good kind of yenta

  • Ask for permission, not forgiveness. Call me old-fashioned, but 9 times out of 10, I’ll seek a green light before making a requested connection. If they’re up for the connect, giving them a heads-up can get you faster, better results. If not, better you (than your connection) get the redirect/no/non-response.

    Help me, help you

    Help me, help you

  • Life is too short for hidden agendas. Start with the end in mind: “a good meeting will result in [___________].” Once you figure that out, let your coffee date in on your game plan. Call me Jerry McGuire, but help me help you….I’ll be more productive if I know what we’re meeting about and can prep.



Mentees, mentors, yentas: Do unto your network as you would have your network do unto you. Go forth and caffeinate!