The First Hand Up Is Not Always the Right Hand

Founders are desperate. Not occasionally, not during the rough patches, but pretty much all the time. They're short on cash, short on customers, and short on anyone who will tell them whether the thing they're building is a good idea. So when someone says "I'd love to help," they grab that hand like it's the last lifeboat on the Titanic.

That's the part of mentorship nobody talks about. We spend a lot of energy getting mentors into the room and very little asking who is actually in there. In a mature startup community, a founder who latches onto the wrong mentor has a dozen other voices to balance it out. In a less mature community, that mentor might be the only voice. If the only advice you get is bad advice, you won't know it's bad. You'll just follow it right off the cliff, politely and with a notebook.

All mentors are not created equal. 

Some have built companies. Some have read about people who built companies. Some are lonely and like feeling needed. Some are selling something, and that something usually shows up around the second coffee.

I know this from the other side of the table. About 20 years ago, I was between things. I'd been sitting on the bench for almost a year, which is a long time to watch the game from the sidelines when you're used to playing. I was getting desperate to do something, anything, and I started talking to people about it.

The advice I kept getting was well-meaning and almost identical: just go work at something. Anything. Get back out there, build your confidence, and the rest will sort itself out. It sounded reasonable. It sounded supportive. It was also exactly wrong for me.

Anything was not the answer. Taking any job would have meant solving for my desperation instead of my situation, and I'd have traded one kind of stuck for another, but with a paycheck. What I needed was someone who would ask what I actually wanted to do next, and why the year on the bench had felt so awful. Nobody giving me that "anything" advice was being careless. They just hadn't been where I was, and they answered the question they would have asked themselves.

That's the risk. A mentor answers from their own experience, and if their experience doesn't match your situation, the advice fits like a borrowed suit. It looks perfect from across the room.

So if you're building a mentor program, and plenty of communities are, start with the founder's desperation. Assume it's there. Don't let the first volunteer win by default. Match founders to mentors with intent, ask what the mentor has actually done, and make it easy for a founder to say "this isn't working" without feeling rude. Better yet, make it normal for a founder to talk to more than one person.

Desperate founders will take the first hand offered. Our job is to make sure there's more than one hand to choose from.