The People Dressed in Grey

What makes a leader? The ingredients of leadership are likely different depending on who you ask. But as this speech by William Deresiewicz, given to West Point’s 2009 graduating class suggests, solitude and the ability to be alone is a huge part of it. 

Solitude and leadership…a very interesting concept. 

It’s not exactly a recent speech, but it’s a powerful one. And it heavily references one of my favorite books, Joseph Conrad’s Heart of Darkness

The references to Conrad’s masterpiece resonated the most with me, not just in the idea of solitude and the importance of being alone with one’s thoughts, concentrating on ideas, and thinking things through–a diminishing trait in this technological age, especially among the younger setnd it’s importance to leadership, but in how Conrad discusses what doesn’t make a good leader:

In between is the Central Station, where Marlow spends the most time, and where we get our best look at bureaucracy in action and the kind of people who succeed in it. This is Marlow’s description of the manager of the Central Station, the big boss:

He was commonplace in complexion, in features, in manners, and in voice. He was of middle size and of ordinary build. His eyes, of the usual blue, were perhaps remarkably cold. . . . Otherwise there was only an indefinable, faint expression of his lips, something stealthy—a smile—not a smile—I remember it, but I can’t explain. . . . He was a common trader, from his youth up employed in these parts—nothing more. He was obeyed, yet he inspired neither love nor fear, nor even respect. He inspired uneasiness. That was it! Uneasiness. Not a definite mistrust—just uneasiness—nothing more. You have no idea how effective such a . . . a . . . faculty can be. He had no genius for organizing, for initiative, or for order even. . . . He had no learning, and no intelligence. His position had come to him—why? . . . He originated nothing, he could keep the routine going—that’s all. But he was great. He was great by this little thing that it was impossible to tell what could control such a man. He never gave that secret away. Perhaps there was nothing within him. Such a suspicion made one pause.

Note the adjectives: commonplace, ordinary, usual, common. There is nothing distinguished about this person.

We all know this guy: The nobody who seems to do nothing yet tells everybody else what to do. The kiss-ass who somehow rises through the ranks. The boss you never want to let slip anything remotely contrary or controversial for fear it will reach the ear of the exact people you never want to hear it. 

In short, Bill Lumbergh from Office Space

Inspiring uneasiness…

Doesn’t it seem as though people like this run the world? Why?

Deresiewicz discusses that it’s what our top, elite (and elitist) institutions teach: how to be what Deresiewicz calls “excellent sheep”:

I sat on the Yale College admissions committee a couple of years ago. The first thing the admissions officer would do when presenting a case to the rest of the committee was read what they call the “brag” in admissions lingo, the list of the student’s extracurriculars. Well, it turned out that a student who had six or seven extracurriculars was already in trouble. Because the students who got in—in addition to perfect grades and top scores—usually had 10 or 12.

So what I saw around me were great kids who had been trained to be world-class hoop jumpers. Any goal you set them, they could achieve. Any test you gave them, they could pass with flying colors. They were, as one of them put it herself, “excellent sheep.” I had no doubt that they would continue to jump through hoops and ace tests and go on to Harvard Business School, or Michigan Law School, or Johns Hopkins Medical School, or Goldman Sachs, or McKinsey consulting, or whatever. And this approach would indeed take them far in life. They would come back for their 25th reunion as a partner at White & Case, or an attending physician at Mass General, or an assistant secretary in the Department of State.

That is exactly what places like Yale mean when they talk about training leaders. Educating people who make a big name for themselves in the world, people with impressive titles, people the university can brag about. People who make it to the top. People who can climb the greasy pole of whatever hierarchy they decide to attach themselves to.

Isn’t that perfect? Jump through hoops…don’t rock the boat…just keep the machine running without, you know, doing anything.

This is one of the problems I have with college, and American education in general. For all the chest-beating about our meritocratic technocracy, it doesn’t teach you how to think independently or critically. 

You really learn how to be a cog in the machine, a semi-functioning drone that will buy this and pull the lever for that without asking questions or causing too much trouble. 

And this attitude is prevalent by just at your small community college, but at places like Yale!

Understand this and understand the modern world. 

It’s part of the reason I am so bad at the kiss-ass game. It’s also why I’m pretty good at spotting the managers who won’t be getting promoted (those who try to improve deficiencies and, you know, do stuff and help their charges succeed).

In other words, it’s the people who seem to focus solely on what other people think of them who rise up through the bureaucratic ranks. 

Which brings up a funny thing about human psychology and the lies we tell ourselves: We crow about wanting “innovation” and “change,” but freak out when somebody brings it. 

And I think I know a reason: We want to be the ones bringing the change, and resent when someone else does instead. 

So while we pretend to dislike these beige managers that make us uneasy, they’re really what we deal with best, because this is what we’re used to. What a sad state of affairs. We don’t want the boat to be rocked either, despite all of our protestations. 

Ray Davies of the Kinks–one of my favorite bands–calls these the “people dressed in grey.” Check out their song “20th Century Man“:

I was born in a welfare state
Ruled by bureaucracy
Controlled by civil servants
And people dressed in grey
Got no privacy, got no liberty
Cos the twentieth century people
Took it all away from me.

Sadly accurate. 

Maybe we should support those who want to shake things up, or at the very least think about said changes, before reflexively dismissing them. If we say we really want change and resent these non-entities, maybe we should act like it. 

Let’s go deep into the 21st century trying to rock the boat so we don’t all become the people dressed in grey. 

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