The Anarchist Employee

Do you have experience managing an anarchist/anti-establishment type? I think there are some good qualities to foster from them (creativity, drive, initiative, curiosity, etc), but at the same time there are some bad qualities I’m trying to avoid spilling over into the rest of the team.
The biggest problem I’ve struggled with when confronted with people like that is my internal struggle.

Specifically, there is something about the anarchist that I can relate to—the courage to speak truth to power, to call bullshit, etc.

As a manager, anything that causes me to be more conscious of the fact that I am the manager—the pointy haired boss from Dilbert, the “Man”, the “Establishment”, the “bourgeois”—I will often respond with internal bias and try to move away from. A-la “Hey, I know I’m The Establishment, but I’m one of you, see!"

And that has caused me to take the wrong approach with “anarchists.” Flat out, I’ve failed here multiple times.

I approach them like this: “Hey, I love that you’re one of our best coders, you really get x, y, and z done well and help the team meet those objectives. And I know you’re super perturbed/annoyed/eschew of management/the system/etc. And mine, and the company’s value, is to never squash contrary opinions. We want to hear from everyone.”

…see what I just did there?

…I just screwed myself.

…because now I backed myself into a corner.

…by giving The Anarchist a huge out in my own psyche, which is, “Hey, you’re speaking truth to power, if I change that, I’m going against the perception and in fact silencing contrary opinions.”

Dumb me. Dumb, dumb, dumb.

Here's an approach with more candor and context: “I love what you have to offer. And it’s often wrapped in a package that doesn’t move the team forward, but instead stalls people due to them starting to doubt the mission. And when you do that, you lose credibility. You, and I, want your expertise to be received and acted on and learned from as many people as possible. That isn’t happening when you say x and behave in {anarchist manner x, y, z}. I recommend instead you do {smiley, nice, good communication}. It’s going to be better for you and the group and help us all be more productive. This time next week we’re going to sit down and I want you to show me your plan for making that happen with deadlines. Let me know if you need some coaching on that.”

Want to have more discussions around topics like this? Check out Marcus Blankenship's tech leadership approach.

What's your anarchist employee story and how did you handle it? Share in the comments below.