Leadership

Grey Hats

I wish things were easier. One of the challenges of being immersed in charities and their leaders is the discovery that there are very few simple solutions for problems. For all the glowing marketing pieces and optimistic strategies, the inevitable truth is that things are pretty much always more complex than they appear. The same is true with people. On our Catalyst Award trip each summer we connect with leaders from a bunch of charities to understand both their work and their personal stories. We intentionally choose some leaders who raise as many questions as they answer. In a couple cases its the leaders themselves who leave us with a lot to discuss. We’re all tempted by simple categories. We want to be able to identify some people as heroes and others as villains. It would be a lot easier if the “good guys” and “bad guys” would wear white and black hats so we could know who to trust and admire. But that’s just not reality. Real people are always complex. We are a mix of motives, abilities, and insecurities. Even our greatest strengths have their accompanying dark sides. We should probably all be wearing grey hats. The challenge of this is deciding who to trust, how quickly, and in what ways. If we don’t want to become disillusioned and jaded we have to develop the ability to see human complexity, allow for imperfection, and still hold people accountable. It’s more art than science.¬†And I still struggle to get it right much of the time. How do you maintain a realistic expectation of people without becoming idealistic or frustrated?