Clowns to the Left. Jokers to the Right.

The middle is where it's at.

Middle management gets a bad rap, and I don’t think it’s deserved. I like middle management! Somebody’s got to manage the TPS reports, right?

By any rational assessment, as a leader I’ve never made it out of “middle management.” I’ve been much closer to the work than any executive would be, yet far less expert at that work than the teams I employed. 

But I don’t really mean to lament this situation. I…kind of like middle management. And I think it can be a useful part of an organization. (I mean, I would think that, right? And I do!)

Smiley face.

Andrew Bosworth (“Boz”), currently CTO of Meta,¹ is a fascinating thinker on organizational development, and quite a skilled writer. Internally at the company he posts about his leadership philosophies regularly. I always thought this was a wonderful nod to transparency.

He also maintains a public-facing website, boz.com, with a lot of this material. I’d highly recommend it. I don’t agree with him on everything — not even close — but it’s always a fascinating read.

One short piece I find insightful is a musing on the frustrations of middle management. 

He writes: 

“To the team you are the voice of management. But to management you are the voice of the team.”

That hits to the heart of the matter. The little smiley-face-shaped graph that he uses to illustrate the piece is also terrific: the “everyone else” label just kills me. Anyway, the ultimate message, the upshot of the piece, basically boils down to…yeah, this is your job so try to do it well! 

Now, coming from someone at his level, a message of “enjoy your life as a cog” might be a little tough to swallow — but I definitely don’t think he’s wrong. 

Look, it can feel like a trap. It can be a trap! You have to execute the directions of someone else, using the labor of…a different someone else. How can you win?

If the endeavor fails, you’re the obvious weak link. If it succeeds, the wisdom of the deciders and/or the skill of the implementers get the credit. At any given time you might seem like friction to the executives and like dead weight to the team.

And none of that is wrong, exactly. Or at least, the potential is always there for it all to be right. I’m sure I, for instance, have been all of these things (weak link, friction, dead weight) at one point or another.

It doesn’t feel good. When it’s going wrong, you can feel like the rope in a game of tug-of-war — you’re not really on either side, you’re just the mechanism by which each is trying to vanquish the other.

But it doesn’t have to be that way. 

As much as I like Boz’s essay, I do think he misses (or barely nods to) one important piece of the puzzle: the role the larger organization has in selecting who actually occupies those middle manager positions.

Mr. Peter enters the chat.

I came up as a practitioner of my discipline, on my way to direction, team management, department leadership and mentoring. As I’ve written about before, I am aware that I was the recipient of incredible good fortune and straight up privilege. But the evolution was also pretty organic. 

I was good at the work (or at least competent at it), and that gave me some credibility. And I was lucky enough to figure out that my real value, such as it was, was in team-building and a brand of “servant leadership” which I always tried to dedicate to the growth and development of those around me. (<- I’m not as righteous as all that in the real world, but I tried.)

And maybe most important: I actually enjoyed that part of the job at least as much as the “work” itself. For me, the most fulfilling thing was knowing enough about the work to recognize skill/talent/potential and nurture it. 

In my career, a move into management made sense. But naturally it came with some risk. And my experience is certainly not applicable to everyone.

The Peter Principle is a well-known observation from the business literature that essentially posits, rather cynically, that people will get “promoted to their level of incompetence.” 

This has a very specific meaning — a successful performer in their discipline will earn promotions, presumably taking on more responsibility, a wider remit, or a more powerful mandate, until they are promoted into a job which has too much responsibility, remit, or mandate, and they don’t succeed. At this point, they will stop getting promoted…and will have landed at their “level of incompetence.” In essence, they’ve succeeded their way into failure.

Kinda feels right, yeah? For sure, we have all seen it play out. Many of us may have rather painfully lived it. I’ve heard it used as a verb: “he really peter principled his way into that one, didn’t he?” In colloquial usage, it seems to really express the truth.

But! The original book upon which this notion is based was satire. It was making fun of management, and books about management, and about notions like…the Peter Principle. 

Tim Hartford talks about this in an article from 2018 (with some quaintly dated references to British politics thrown in). He calls The Peter Principle “a joke taken seriously.” But he’s curious: could this thing that feels truthful — but was first documented as mockery — actually have some factual basis?

He cites a study that shows The Peter Principle may very well be demonstrably true, but the responsibility for it is maybe misunderstood. The study looked at a large sample of software sales teams:

“The authors of the paper discovered that the best salespeople were more likely to be promoted, and that they were then terrible managers. The better they had been in sales, the worse their teams performed once they arrived in a managerial role.

What’s more, people were not promoted for behaviour that might seem correlated with managerial ability — in particular, those who collaborated with others were not rewarded for doing so. What mattered were sales, pure and simple.”

Just because it’s satire doesn’t mean it isn’t true. Obviously! The best satire shines a light into some dark places, sometimes. What I think we find here is not that The Peter Principle is wrong (we all know that it isn’t), but that it lays the blame in the wrong place.

It blames individuals for the failings of their organizations.

Be the grease, not the friction.

The invocation of The Peter Principle isn’t constrained only to the middle manager class. For sure we’ve had this thought about executives, too. 

But it is cruelest, I think, to the “everyone else” in Boz’s graph.

Sure, we are each and all responsible for doing what we can to put ourselves in a position of success — I do not mean to wholly absolve someone for grabbing the reins of a horse they don’t want to ride or can’t control. 

But I also empathize a lot with ambition and the reasonable desire to move ahead in one’s career. If the organization only gives you one path to do that, what are you supposed to do? Blaming poor middle management only on the middle managers themselves is short-sighted.

The key is to ensure that strong performers have a path of advancement other than just into management. If the only way you can reward someone is by moving them into a job they won’t like and won’t be good at, you’ve got a structural problem, not a personnel problem.

At the same time, being able to recognize potential and promoting the right folks into leadership is fundamental to a strong team. They are out there! Credible subject matter experts who are more interested in their chance to have a multiplier effect than individual contributions do exist. Help them succeed!

P.S. A note about the title of this essay: I know in the US politics are absolutely saturating our consciousness right now, but that’s not where I’m going. Just quoting the old song. (But do vote!)

1. I had the good fortune to work with Bosworth as Facebook. Look, I’m not intending to name-drop; in five and half years there I had one meeting directly with him and he wouldn’t know me from Adam. But I did work a lot with his immediate staff, for what it’s worth.