Why Pessimists are Awesome

The most frustrating person on your team might be the difference between success and failure.

I’ve had the pleasure of directing many programs and teams over the last 10 years, and all the best ones have had one role in common: one type of person who occupies an important spot in the group.

It’s the pessimist.

He’s the one you’re nervous about convincing when you’re bursting with the best idea ever. Where you see opportunity, he sees risk; where you see the potential for goals to be achieved, he sees the potential for unintended consequences; where you see a clear priority, he sees a different one that’s being threatened.

For someone like me, that guy is the most important person in the group. Like most reformers and activists, I’m an ideas guy. When I think I’ve figured out a solution to a major problem, nothing can move fast enough to make that idea a reality.

These traits mean I like to make things happen. They also mean I’m dangerous. If I’m not balanced by something, for every unprecedented achievement I might cause half a dozen catastrophes. The worst thing about people who want to make a difference is they usually do.

Take the ideas people of the environmental movement. Some of them could use a pessimist or two on the team. Remember a number of years back when you were a terrible person if you used paper bags for your groceries? You evil tree killer. You were supposed to use plastic. Except, oops, turns out plastic bags by the zillions are terrible for the environment. Remember when you were a terrible person for using paper towels in a public restroom? (You still are–for now.) You’re supposed to use electric hand dryers. Except, oops, apparently the most effective one we’ve come up with is a massive spreader of germs, or at least that’s the new headline. (The social justice warriors of the land of Flu are celebrating this triumph of newfound social mobility.)

Or take the idea person of Star Wars, who in the 1990s decided to take his brilliant brainchild in a new direction, with top-of-the-line technology and filmmaking techniques. He called the result The Phantom Menace…okay, ‘nuff said.

The point is, when people who want to make a difference don’t have pessimists slowing them down, the line between change and actual reform can get fuzzy. They can get wedded to a progressive-sounding concept surprisingly quickly, get more invested in its success than it deserves, and before they know it, Jar Jar Binks has traumatized an entire generation. (As bad as people can be at choosing what hill is really worth dying on, they are even worse at asking what the consequences might be for the hill.)

What I’ve loved about having “pessimists” on my teams is that usually they aren’t actually pessimists, even though they may seem that way most of the time. The ones I’ve worked with are people who have taken the time to learn to love the thing we are working on (the cause, the program, the city, etc.). They are concerned about not losing something great in the quest for something better—so they make me answer the tough questions before they’ll get behind a new direction.

Often, the difference between success and failure is whether I answered them.

Brian Brown
Brian Brown loves building the environments, habits, and networks that make people thrive. He is the founder of Humane Pursuits, where he writes a featured column and edits the Give channel. He started his consulting company, Narrator, to help great mission-driven organizations modernize and grow. He lives with his wife Christina and son Edmund in Colorado Springs, where they mix cocktails, hunt for historic architecture, and see how many people they can squeeze into their house for happy hour.

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