On Leading with Greatness

Leadership and writing have some direct parallels, not the least of which is that when done well, people don't notice.

Slide 321 of the most exhausting PowerPoint I ever sat through taught me almost nothing about advising students—but it accidentally taught me much about leadership. So did a brilliant, infuriating Korean student who could humiliate me with grammar rules but couldn't write a single clean sentence. Both stories point to the same lesson: you can know everything and still not know how to do anything.

Why do we impose thoughtless, unnecessary, even harmful rules on ourselves and our organizations? Tradition, inertia, inherited habits, the hidebound predecessor whose practices nobody questioned. Over time these ad hoc rules harden into identity—"this is just who we are"—and can even manifest as what I call bureaucratic compulsive disorder.

They're garbage rules that squander time, energy, and opportunity while we pretend they're values or identity.

This week I draw on Bob Newhart, Viktor Frankl, Bob Dylan, and a hoary tale about a beef roast to make the case for a leadership practice as clea...

The leadership gurus I call the nabobs of negativity insist leaders need to learn to say "no" more often. But is the big problem in leadership truly leaders who don't say "no" enough, as the nabobs would have it, or leaders who say "no" too often?

Doing the same thing over and over and expecting a different result isn't insanity, not when it benefits the bosses.

Abraham Lincoln is often cited as an exemplary president for leaders to emulate. While that's true, his leadership is far more nuanced and complicated than most people realize, and therefore he's a more useful model of leadership. Honest Age is an honest model of leadership.

Just because it’s infinitely difficult to contemplate the infinitesimal doesn’t mean that you shouldn’t learn all you can about Quantum Bossing—QBossing. It’s a great way to use everyone’s (even your own) profound ignorance of science to justify just about anything. And if you can convince everyone of an absurdity, such as you’re in two places at once, they’ll eventually give up, give in, and pledge themselves to you like, say, a quark to maybe a gluon.

Want to hear about my dream? Sure you do.

The exasperation, anger, disgust, frustration, and helplessness the dream evoked recalled my anguish working at some pretty screwy universities. In fact, I could point to particulars in my lived experience that directly paralleled my dream.

Systems thinking is a handy skill for a leader to have, and I suspect a lot of leaders are systems thinkers even if they never thought of themselves as such.

So, let me hit you with systems axiom 1: There is a correlation between systems thinking and successful leadership—keeping in mind that correlation is not causation.

What do you call someone who sits back in the face of wrongdoing?

Complicit.

Leadership is just another type of human relationship.

Leadership is not much different from friendship, animosity, acquaintanceship, or even romance. It harbors no mysteries that any of these or other human relationships hold.

What can a conscientious leader dedicated to human decency do to get a more objective self-assessment than private reflection will provide?

Let me ask the question more eloquently: who calls you on your s**t?

There is no leadership without justice.

If you’re a leader, the means to your goal is simple: just act justly to achieve justice.

Much bullying, even the vast majority of bullying, serves no real purpose at all. Think of the schoolyard bully. After he has successfully terrorized all his peers into submission, he really has no reason to continue bullying on a regular basis, but he does.

The story of Odysseus and his monstrous confrontations offer lessons for leaders, both good and bad.

What does it really mean to think and write about leadership?

The best writers on leadership—even if they don’t see themselves this way—are in fact moralists in that they concern themselves largely with questions of right and wrong, good and bad.

One aspect of leadership that rarely gets its full due is its integral relationship to power. The pursuit of power (as with its counterparts, wealth and fame) can be corrupting but not necessarily so. While power offers myriad opportunities for abuse, it also presents positive possibilities.

Here’s a dirty secret that few acknowledge inside or outside of education: teaching only takes place when learning takes place. In other words, unless someone actually learns, no one has done any teaching. For what is teaching without learning? One hand clapping.

It’s the same with leadership. You can’t be a leader if no one follows. Seems obvious, right? You can’t lead the cavalry charge if there is no cavalry. But we make that mistake all the time.

he First Follower Effect: How Fearless Followers Make the Leader

Every Leadersh...

Have you ever seen the sitcom Abbott Elementary? Among the many memorable characters populating the school, my favorite is the principal, Ava Coleman. To say Ava is self-serving is an understatement, but she also can be outward looking if only when you least expect it. Overall, though, she’s simply a terrible boss and therefore a lousy leader for her struggling little school. Even so, Ava’s words and actions teem with sharp revelations about the impact crappy bosses have on the day-to-day workplace.

A Festive Parody for this Season of Joy

Without the core—the why and how of it all—most would-be leaders struggle to find generic strategies that fit their circumstances and implement them successfully over time. Forget adapting.

Real trust takes a lot more than a momentary exertion of empathy. In reality, the mechanics of trust can be complicated and dynamic, which is why the best leaders have a profound appreciation for trust and carefully cultivate and nurture it.

Despite everything we’re told (and perhaps believe) greatness doesn’t drive lasting progress. Goodness does. Greatness as we rate it has to do with one’s prominence, such as position, wealth, influence—all fleeting and limited. Meanwhile, true goodness tends toward the humble and yet can be far more persistent and powerful.

For years, I struggled to accept compliments with the grace they deserve. When praised, my mind would grumble, “What’s their angle” or “If only they knew…” I’d tell myself I needed to dismiss their recognition so I could “stay humble,” which really just reflected a limiting belief that I'm not deserving.

I have a confession to make. I’ve been misleading you—maybe even lying to you—for years. The fact that I’ve been lying to myself all that time doesn’t make it any better.

The lie I’ve been telling us all is that great leadership will lead to business success. In fact, I know of no studies or slam-dunk examples that definitively demonstrate this claim. I’ve also said that bad bossing is incompetence in practice, which I maintain, but we can identify plenty of objectively bad bosses who are wildly successful.

The b******t is that so many people must seek mental health treatment of all sorts because of their jobs. No one should have to go to therapy because their boss is a dipshit bully, their colleagues are creeps, or their whole organization is a cesspool of toxic behavior. And yet we do. I’ve done it more than once and because of more than one noxious employer.

Great leaders know that creating general rules to address a single, narrow issue can result in unfortunate outcomes throughout an organization. It’s like taking a sledgehammer to a fruit fly.

One of the most challenging aspects of leadership is countering, neutralizing, and helping others cope with bullies. Every bully is a fraud—a weakling and a coward—and deep down they know it. We all do.

Have you ever seen the British version of The Office? The office manager, David Brent, presents himself as a benign leader, but he’s aggressively benign, and the show demonstrates amply that such a beast can be as toxic as the worst boss.

Humans love categories. We can’t get enough of slicing and dicing things into small parts and putting them each into their own cozy cubbyholes. We do all this because categories help us make sense of the world.

Classification serves a useful function,but such systems lack an inherent basis in reality. Great leaders recognize the mixed nature of our drive to taxonomize. Leaders also know that our very humanity renders classification ultimately counterproductive.

The best leaders think about systems of thought—their own and others’—to understand how leadership functions. They consider systems of thought when they make decisions or need to persuade. They contemplate when to press those systems and when to ease off.

I call this technique “the buy-In boomerang.” It’s a logical turnabout that uses someone’s own stated standards against them. It’s a way of neutralizing a passive aggressive bully by getting them to buy into your argument. This technique draws on established psychological principles like commitment and consistency, but it specifically applies it to workplace bullying where evidence is ambiguous.

Call them what you will: conciliators, moderates, normies, or rationalists, many of these people who guard the status quo constitute the extremist middle. In politics, they’re called “radical centrists,” but they pop up in all sorts of scenarios. They’re radical because of their ferocity.

Leaders are individuals, but their individuality is almost irrelevant when it comes to their leadership success. The best leader is, after all, just another team member.

For a leader, what could be more wonderful than heading an effective organization that has earned a top award? Such collective success can be more satisfying than any individual prize.

Leaders think a lot about success, so let’s do that. Success is obviously the goal, but what do we mean by it? All too often we focus on the wrong kind of success or the wrong metrics of success.

What a spectacle! A 70-something-year-old white man commanding the stage as he bellows into a microphone. He holds this packed stadium in thrall to his every utterance. The crowd is in raptures. His crowd. They’ve heard all he has to say before, and they want to hear it all again. They cheer, they chant, and they yell his words back in sync to him.

This is not some tawdry political rally, though, and the man on stage is no bumptious demagogue. He is Bruce Springsteen—“The Boss”—performing at a recent concert I attended. And I can tell y...

Great leaders think about legacy—what values and behaviors they’re passing down over the long haul, to whom, and how those recipients will carry what they learn into the future. Only this way can leadership have a positive effect beyond the immediate. Like all aspects of leadership, legacy thinking is imperfect, but it’s always preferable to the toxic bequest of bad bossing.

While there are traits and factors where leaders and philosophers significantly diverge, they also have a great deal in common. It behooves the leader to consider the philosopher’s way and embrace it wherever most beneficial while understanding the differences between leadership and philosophy.

With all the leadership advice (most of it quality) cluttering social media, our bookcase shelves, and our Audible lists, you’d think that we’d see a profound and widespread positive shift in how people in general manage. I guess things have gotten a bit better in spots, but overall the same assumptions and practices—the same bossing ethos—that have always held sway remain set. Most people in positions of authority cling to mere bossdom.

Let’s create a little thought experiment. Let’s imagine a continuum stretching from the bossiest of bosses on one end to the most virtuous of servant leaders on the other. Contemplating this continuum reveals a paradox of perception. Here’s how the paradox works: the more an individual’s behavior leans toward the virtuous leader end of the continuum, the more we perceive their flaws and inconsistencies no matter how minor or anomalous.