Sometimes the Best Leadership Move Is Finding Someone Else to Say It

I need to confess something. I spend parts of every day searching for new leadership moves to help move my community forward. For years I assumed my best ideas about startup communities would land hardest at home. I live here, I show up, I know everybody, so surely people would listen to me. That is not how it works. I have said the same sentence in my own city, to my own people, and gotten polite nods and a quiet "what's he really after?" I have said that same sentence in another city, to a room full of strangers, and watched someone write it down like I had just handed over the Dead Sea Scrolls.

It turns out being a prophet in your own city is a rough gig. The old line says no prophet is welcome in his hometown, and I would like to add that the hometown also suspects the prophet of angling for something. When you are the one pushing for change in the place you live, everyone assumes you have an agenda. Maybe you do. Maybe you want a program funded, or a building filled, or a seat at the table. Even if you honestly want nothing, people will invent something for you, because that is easier than hearing the actual message. Familiarity is wonderful for friendships and terrible for credibility.

Here is the part I found humbling. The message was never the problem. The messenger was. I have watched a city's leaders ignore the same advice for three years from a local, and then embrace it in 20 minutes when a visitor said it from a stage. Same words, same slides, same awkward joke about tree forts. The visitor just had one magic quality, which was having no stake in the outcome. Nobody wonders what a guy from out of town is trying to win. He is flying home the next day.

I have come to terms with the fact that this is most of what I do. I did not set out to be the outsider who says the obvious thing out loud, but I keep getting invited to be exactly that, and the more I look at it, the more it makes sense. Leaders in a community are buried in history, in old grudges, in who accidentally did what to whom at the 2014 pitch night. An outsider walks in with none of that baggage. I can say "your community needs more engagement, not more events" and nobody has to wonder whether I am taking a swipe at the person who runs the events.

The flip side is that I do not get to be that person at home, and I have stopped being sore about it. My job at home is different. It is to show up, be useful, make the introductions, and quietly keep my agenda out of the room. And if I am being honest, my job is to go find someone from somewhere else to say the hard thing so I do not have to. Some days that is the smartest leadership move I make.

So if you are trying to move your own community and feel like you are talking to a wall, try something a little humbling. Stop pushing harder and start borrowing a voice. Invite someone from another city who has seen your problem somewhere else and has no reason to flatter you.

And in return, be that outsider for somebody else. Somebody in another city is stuck being the prophet nobody believes, and a few honest sentences from you could change the whole conversation.