any damned fool can be optimistic

This post’s title is a direct quote from a member of my team, talking about his role as risk-identifier, gadfly, pessimist and occasional nay-sayer.

I recall many a project-management-of-people class touching on the idea of pessimist as a useful team role, to the point of designating someone to pick apart all the reasons a solution might not work. I assume there’s some organizational behavior research behind this recurring idea, too – there’s almost always some form of psychology at the heart of any simplified management truism.

That notion isn’t unique to projects or even “management”; deBono’s thinking hats thing, for instance, includes a hat of “critical judgment”, which I like to think of as the hat of angst and risk aversion.

In any case. I don’t believe optimism is foolish. It can be, but it’s just as likely to be a result of experience and trust. You get through one cluster of a problem, and you begin to see paths through others. It’s not a failure to see problems so much as a belief that they’ll get solved.

Where I see pessimism being truly helpful, though, is not in the popular domain of risk (sure, that’s handy, but you can get to risks from a lot of different directions, and getting too critical or analytical can paralyze a group). It’s the pessimist’s willingness to be an iconoclast, to stand against something. Because. Standing against is still taking a stand. Even a wobbling uh, guys, I don’t think this is going to work stance is a way of injecting dissent into a group conversation. That’s the whole idea everyone gets from the Asch experiment, right? One black sheep, and suddenly it turns out sheep are like My Little Pony and come in all colors.

Dissent, used well, is how we get a whole picture as a team. That is – sometimes groups don’t even notice they’re falling into consensus too easily. It takes a pessimist – someone brave or smart enough not to fear conflict – to throw up the 40 point card in planning poker and point out how much the group doesn’t understand yet. Just one voice of dissent from an apparent agreement, and it turns out the issue is much more complex, and is actually being understood in several different ways. That diversity of thought contributes to teams outperforming individuals, and it’s often the grumpy pessimist who kicks that off.