Why I regret being a nice boss

Not all businesses require that level of micromanagement. But establishing which rules are non-negotiable, and making sure that everyone understands them with crystalline clarity, is a matter of fairness. It’s the thing I wish I could go back and do over—not because it would have saved my business, but because everyone, myself included, would have been so much happier. I allowed my coffee shop to become characterized by permissiveness. Some took advantage of this permissiveness by making up excuses for being late, or by trying to do as little work as possible. Those who didn’t take advantage became resentful of the other employees, and of me. It brought out the worst in everyone.

Recently, I’ve been reading a lot about failed and despotic governments, and I’ve realized that these regimes have some parallels with failing businesses. The most fascinating parts of David Remnick’s account of the fall of the Soviet Union, Lenin’s Tomb, deal with the ways that depraved systems cause ordinary people to behave badly: “The system made beasts of them,” Remnick writes. Most people are only as good as their systems allow them to be. In my case, by trying to give my employees personal freedom—by trying to be nice—I created inadequate systems that didn’t allow them to thrive.

The idea that we must tell adults what to do and exactly how to do it is a hard pill to swallow for most.