On Leading with Greatness

Let’s start by stipulating that you are busy, very busy, very, very busy even. What with the kids and that damn dog and your nagging boss, not to mention the sheer number of tasks you are expected to complete in a given work day. You’re busy. I get it.

Back in April of 2021, the business and entrepreneurship guru Sahil Bloom posted on Twitter a simple but profound observation.

The world wants you to be normal. Our systems and institutions are all designed to make it easy to be normal. Maintaining your distinctiveness is possible, but it will require effort — painful, constant, relentless effort. But stay the course. You’ll find it’s worth it.

Bloom sets himself up here as an enemy of the normal, of the comfortable, of the same-old-same-old, of the status quo as he advocates for individuals and organizations to lean into their distinctiveness in order to differentiate themselves from the herd.

John Henry was a steel-driving man, or so the song goes. A figure of American legend and the subject of many heroic songs and tales, John Henry was a Black railroad worker in the 1800s who challenged a newfangled steam-powered drill to a contest. Henry, according to the lore, won the competition but died soon after from the strain.

That model of labor, the man who can just push himself further and further — suggesting that all effort is just a matter of willpower — is a myth that still burdens our workplaces and our approach to work. It’s the idea that if we just do more — one more thing — productivity will increase, as though we will never reach the point of diminishing returns.

Much of my perspective on the working world and on leadership has been shaped or warped by my experience as a faculty member and then a dean at a small university outside of Baltimore. It’s a good part of the reason I have such a low tolerance for incompetent leadership and have made it my goal to guide leaders to greatness. The university had once been a dynamic place, but it had long fallen into dysfunction and moral corruption by the time I left. Therefore, many of the lessons that I took away were what I call negative paradigms, an opportunity to learn from others’ mistakes.

To be sure, I have made plenty of my own instructive errors, but operating in that environment was like tap dancing in a minefield while bombs dropped from above. It was impossible to know what was a misstep and what was just bad luck.

Every leadership problem is a teaching problem.

In other words, the same skills one uses to teach are precisely the ones an effective leader needs. Now, when I talk about teaching, I am drawing on my background as a college professor and administrator, but please don’t picture a sepia-toned image of some tweed-clad egghead behind a podium perched on a platform droning on as students attempt to capture his (yes, his) pearls of wisdom in their notes.

The squirrel is a curious creature that is one-third rat, one-half furniture duster, and four-fifths dog toy. I have always enjoyed the antics of squirrels although I have also rained curses upon them as they raided my bird feeders. As thieves, they are relentless and clever as you may surmise from the many squirrel-proof feeder designs on the market. The squirrel can climb anything you hang a feeder from. If you install some sort of baffle to deter climbing, the squirrel will leap down from above. A few fancier feeders are designed to seal shut under the squirrel’s weight. Some squirrels, though, will eventually figure out how to distribute their weight so that they can feast. Relentless.

You are no doubt aware of the series of megahit movies that started with The Matrix in 1999. Here is a brief overview for those who — due to a lengthy coma or prison sentence — remain somehow ignorant of the premise of the original movie: Sometime in the future, humanity has been linked en masse to a simulated reality called, you guessed it, “the matrix,” which is run by artificial intelligence. (As I wrote that sentence, I swear I heard Alexa giggle.

The sunk cost fallacy assumes that because something warranted a significant financial investment in the past, it is too valuable to do away with no matter the evidence.

Similarly, what I call the sunk virtue fallacy assumes that because a significant investment of effort in the past was effective, it is too valuable to do away with, no matter the evidence. Clinging to sunk virtue can be like clinging to a half-wrecked boat. You are lucky to keep your head above water.

Pam was a senior manager with ambitions. She had climbed higher in her organization than she had ever before imagined, but now, heady with that success, she could easily imagine climbing higher still. What got her to this level was tenacity and focus, never being satisfied with anything less than perfection. She always got the job done at any cost, and she made damn sure others saw her that way.

Do you know what a bootstrap is? It’s that little loop or tab at the top of a boot. It may in the back, or there may be one on each side. It’s there to help you pull the boot onto your foot.

Do you have a pair of boots like that? I want you to try something with them. Go ahead and get them. I’ll wait.