On Leading With Greatness
On Leading with Greatness
How to Be as Best Bosses Be
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How to Be as Best Bosses Be

A (W)Rite of Spring (or Fall for the Down Unders)

SIR, I admit your gen’ral Rule
That every Poet is a Fool:
But you yourself may serve to show it,
That every Fool is not a Poet.

Alexander Pope (translator)

A muscular man in a blue business suit looking forward with his hands on his desk. He looks very angry. In front of him is a large gold cup trophy with the words “Best Boss” etched along the bottom.

How do you acknowledge the change of seasons? I always feel inspired by the arrival of a new April. The first day of April is a time for celebration, frolic, and playful reversals. In that spirit, how about instead of an essay on best leadership practices, we take a look at how to be the best boss possible? As a sort of public service announcement. After all, bosses are people too (at least in the biological sense).

Frankly, most of my writing on leadership is pretty useless to the typical boss. That is, unless they do the opposite of what I advocate. Still, I would advise bosses and aspiring bosslets to really take in all that great leadership advice out there. Make sure you understand it through and through. That way you won’t accidentally follow it in a weak moment.

For instance, when I say that great leaders rely on character strengths like human decency, the perceptive boss will immediately know that human decency is anathema to their own best practices. Indecency is a best boss’s virtue. Indeed, the very best bosses could well be described as “real creeps.”

I’ll give you an example. I had a truly excellent boss who really went the extra mile when it came to undermining her people. She was a college president, and I was a vice president. One time, in a private meeting with her, I praised an untenured faculty member for bravely sharing that he suffered permanent impairment due to an accident. The president’s instant response was to declare that we should fire him for being disabled.

After a few nonplussed moments of silent blinking, I decided that she was not just making some sick joke. I sprung into action, arguing that this man was incredibly dedicated and smart and had in fact recently won a teaching award. None of those facts moved her. No, she only backed down after I pointed out that firing him would violate all sorts of laws and result in a nasty lawsuit, which we would surely lose.

That there, my friends, is some ace bossing from a college president. Her first impulse was to do the opposite of the decent (or legal) thing and sack a highly competent employee simply for having a disability. My job then, as a leader, was to protect this faculty member.

See how that works? A best boss acts like a jerk, so a leader has to unjerk the boss’s jerking. Hence, the main rule of best bossing is to do the opposite of what a leader would do or maybe do something a leader would never even think to do.

As always, though, there’s an exception. Sometimes a wily best boss will seemingly do what leaders do, but only in order to misdirect and gaslight.

Another boss I had used to behave in ways that suggested he might actually be attempting to lead. He even used the language of leadership and pretended to have solid values that he practiced. In fact, though, he was an inveterate liar who broke promises as a matter of course. He also demanded that his lieutenants adhere to a strict yet ever-shifting ethical code that he and his favorite lieutenant regularly flaunted.

Now that’s how to be a best boss! Just pick any standard bit of leadership advice out there—that leaders should listen and communicate clearly, that they should grant team members autonomy, that they should be transparent, that they should not play favorites, etc. Whatever it is, I bet I have an example of this guy pretending to adhere to it, demanding it of (all but one of) his lieutenants, and then doing the opposite.

This guy used his knowledge of leadership practices to distract from the fact that he was not following them. I really have to hand it to him. He was a one of the best of my best bosses, a real hypocritical bastard.

While leadership advice can serve as a useful guide for how not to behave, it’s worth laying down some clear rules for best bossing. This way, bosses won’t stumble into some moral compunctions or, worse still, mistakenly practice sound leadership.

As a service to baby bosses who aspire to be best bosses and to established bosses who want to brush up on their best bossing practices, I want to share my best bossing manifesto.

MY BEST BOSSING MANIFESTO

Preamble

The world is a volatile place, marked by difference and scarred by the clashes that difference engenders. In such a world and at such a time of global turmoil, we comfort ourselves by knowing that some universals still prevail.

For instance, in every culture in every corner of the world, you can rest assured that some individual or set of individuals will use their superior position or strength to suppress or even pummel those in an inferior state. You also will find signs everywhere of people who would rather score political points than actually get things done or make progress.

As heartwarming as these examples are, one constant universal outstrips them all: the persistence of best bosses and best bossing behaviors. But is it enough? Can we ever have all the best bossing we need in the world?

I say, “nay.” There remains plenty of mayhem to sow, and we need expert sowers to do so so that the world will cease to remain so so-so. Therefore, here are the best practices of best bosses disassembled into four actionable principles.

The Four ‘Cs’ of Best Bossing

Corruptness: By “corruptness” I don’t mean dipping into the till or accepting bribes although I would never want to deny you your little indulgences. No, I’m referring to the opposite of having good character.

Of course, everyone claims to have a good character, just as everyone claims to be an above-average driver. But we know that’s all nonsense. And when it comes to bossing, character is as useful to a boss as a bicycle is to a fish.

Best bosses embrace their inner corruptness whether by undermining their own values or simply not having any. Best bosses are morally bankrupt by default.

Confusion: By “confusion” I don’t mean that best bosses are confused although I don’t not mean that either. I’m referring to the opposite of practicing effective communication.

Best bosses use poor communication to foment disorder and keep everyone off balance. It’s a brilliant strategy, really. If you communicate in a confusing way—blathering on and on and tossing word salads—no one can ever hold you to your word.

You can then claim they misunderstood you, that you were “just joking,” or you don’t remembering saying what you said. If it works for nefarious politicians, it will work for bosses. Confusion is the best boss’s best buddy.

Coercion: By “coercion” I don’t mean forcing someone to do something although there’s really nothing wrong with that. No, my meaning is more subtle as in the opposite of the willingness to compromise.

Compromise is a give and take, which means everyone must give up something to come to an agreement. Bosses love to feint at compromise, but in reality they rely on coercion.

In addition to brute force, coercion can take the form of deception, cheating, or chaos making. Does all this sound a bit like bullying? No worries. Everything is allowed when you’re a boss, especially bullying. Pro tip: the only thing best bosses should ever compromise is their values if they have them.

Competition: By “competition” I don’t mean a fair contest with a gracious winner and a conciliatory loser. No, in fact, fairness is irrelevant. All that matters is winning the zero-sum game, the opposite of the win-win scenario of collaboration.

Best bosses exploit the winner-take-all nature of competition to gain the upper hand through any means necessary. Nothing is shared, and everything is up for grabs. To the best bosses, anything you gain somehow takes away from them, so they must have it instead.

Best bosses practice the politics of power rather than the politics of possibility. All that matters is dominance, so collaboration is out of the question. Every scenario is a battle that they must win at any cost.

Manifesto Finito

Best bossing is really that simple. Just be sure to practice corruption, spread confusion, coerce people into doing things, and compete ruthlessly. People really admire these behaviors apparently, given how ready they are to reward the best bosses who practice them.

Whatever you do, if you want to be a best boss, don’t give into the temptation to have a decent character, communicate well, compromise fairly, or (shudder) collaborate. Leave that nonsense to actual leaders.


If you’re an aspiring leader reading this manifesto for some reason, I guess you would just flip it on its head. That way you could do right by your people. But that’s too much effort for best bosses. Being a jerk, unleashing chaos, bullying, and ruthlessness are the way of the successful best boss. It’s easy, fun, and rewarding!

Leaders face more of a challenge. Leadership requires solid values backed by consistent behavior and courage. That means leaders have to start with introspection, and nothing has more of an ick factor for a boss than candid self-assessment. If you’re the self-reflective type, I’m sorry; you’ll never be like a boss at all, and good for you!


Do you practice the 4Cs of Best Bossing? Why?

Leaders differentiate themselves from bosses through their values and their behaviors, and I can help.

Unlock the Great Leader Within! Download my free resource, the Transform To GREATness Toolkit, now!

Unlock Greatness Now!

I look forward to hearing from you.

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About Dr. Sal

I founded Guidance for Greatness to mentor rising professionals after serving 30 years in higher education as an English professor, dean, and VP.

In my speaking, writing, and coaching, I blend academic credentials (Ph.D. from Toronto, certificates from Harvard and ACE) with practical coaching certifications (Tiny Habits, Thrive Global) to offer something different: leadership development built upon human decency.

My mission? To guide today’s managers to become the next generation of great leaders.

I offer practical, values-driven strategies so that managers can lead authentically.

Why? Because great leaders aren't just effective managers—they're teachers whose example makes a true difference in the world.​​​​​​​​​​​​​​​​


It’s almost here!

Discover the practical strategies that transform good managers into exceptional leaders. Look for my new book, Greater than Great: How to Excel in Leadership through Learning, Logic, and Life to Make a True Difference in the World, in early 2025!

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