It’s probably weird but my favorite character in the Winnie the Pooh stories is Eyeore. I still remember this from the one of the books:
“Good morning, Pooh Bear,” said Eyeore gloomily. “If it is a good morning. Which I doubt.”
Despite being clinically depressed, Eyeore is invited along on all their wonderful adventures. It’s a testament to friendship, acceptance, and love.
Eyeore presents some leadership challenges. There is likely at least one full-blown Eyeore in your group. Overly pessimistic, even when things are fine. Imagines only worst-case scenarios. Convinced of impending failure and capable of self-fulfilling prophecies of doom.
You might have a little Eyeore in yourself, too. Not all the time maybe, but sometimes.
Eyeore can be a great contributor and probably has an important skill or experience your group needs. Eyeore excels at spotting potential problems, and fast. Eyeore can be a great counterbalance to your hyper-positive team member who believes everything will work perfectly, first time, every time.
But Eyeore is not a leader. When you’re letting your inner Eyeore come out you’re not being a leader, either.
Eyeore systematically looks down and in, rather than up and out.
Remember, too, that Eyeore likes being Eyeore, even if he says he wants to be different. It’s rare to see a transformed Eyeore, because his self-image must change so dramatically.
Bottom line: Bring your Eyeore along with the group. Encourage him or her. Exploit their capabilities and insights. But don’t give them the reins to any projects or significant leadership roles.