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Why great leaders are always kind—but not always nice

When leading my company, Ashley Stewart, forward after a run-in with bankruptcy, I became convinced that kindness and math were our keys to success.

Trust me when I say I fought hard to find another word for kindness. Any other word. At the same time, given everything we’d been through at Ashley Stewart, I felt reasonably confident that my colleagues, who had literally been through a battle for survival with me, understood what kindness was. They had lived it, immersed themselves in it. But could kindness last?

Could kindness scale? Could kindness continue to help sustain and drive our bottom line? At some point, too, I needed to reconnect the company with the world beyond our immediate ecosystem of colleagues, customers, and vendors. What would kindness mean for future colleagues, and business relationships, who had not seen us in action, up close?

We all know that pop culture sentimentalizes kindness, while the business world dismisses it. Lemonade stands staffed by plucky kids in sneakers and overalls? No problem. But in the adult workplace? No. Armor on. Kindness is embarrassing, decidedly uncool. A curriculum centered around kindness isn’t exactly dominating the world’s business schools either.

But why not? Kindness hasn’t been shown not to work in business. Maybe it’s because kindness, almost by definition, resists being reduced to a single number, which makes it difficult to run correlation and causality analyses. Or maybe because kindness is being improperly defined.

Try as I might, I couldn’t come up with a better word. There isn’t one, except maybe love, which is related to kindness, but not the same. Love is intimate, and personal, whereas kindness can be exchanged by complete strangers. Meaning, kindness is much more scalable than love.

So how do you define kindness? It’s not easy. Kindness isn’t meant to be put in a box. It’s a noun that should also be a verb—to kind. Kinding. Maybe that’s part of the problem.

First, let me point out that over the centuries, a handful of extraordinary leaders—think about it, you probably know whom I’m referring to—have created world-changing movements grounded in the philosophy of kindness.

Kindness is transcendent. Some of the world’s leading philosophers, like Jean-Jacques Rousseau and Adam Smith, whose thoughts inspired then-radical concepts like liberty and free markets, wrote openly about kindness during the Age of Enlightenment. Also, if Sun Tzu, in his book The Art of War— which today’s global military and business leaders still dog-ear, despite it being written in roughly the fifth century B.C.—can reference kindness and compassion as core ingredients of leadership, how weak or beside-the-point can kindness be? So, why is kindness often marginalized and misunderstood today?

To answer, let’s see if we can first agree on what kindness isn’t. Kindness is not niceness. Kindness is not random, despite all those bumper stickers. Kindness is not accidental. It is not martyrdom. What, then, is kindness? Kindness is intentional. Kindness is both forceful and malleable.

Kindness is relentless and steady like flowing water. It requires a person (or an organization) to operate and act in a certain way, beyond mere good intentions. By calling on us to behave in ways that might, on the surface at least, run counter to our self-interest, kindness also requires courage—and a leap of faith.

When you think about it, kindness fundamentally involves an exchange, or a series of exchanges, with one or more living beings. Maybe that’s why game theorists write about kindness as a strategy. It’s an investment in a person and in a system. Kindness implies the expectation of some form of “return,” but in this case, the “return” is nontransactional.

Kindness is therefore grounded in some degree of hope and optimism for the future. Over the course of one or more of these exchanges, value is created above and beyond the obvious exchange of, say, the dollar bill handed over for a cup of lemonade. I believe that the best word to describe this value, this nebulous asset, this positive externality, is goodwill.

How do you know when something of value has been created? By the way it’s received. You can’t create value by yourself. You need a partner, or a counterparty. It’s those others who determine if your how and what actually created value. Again, kindness is an exchange.

That’s the tricky thing, though, isn’t it? The value created by kindness is intangible. You need to feel it. And sense it. You need to use all your human faculties, not just your eyes. You need to be receptive to that warm, good ache spreading in your chest. You need to be present. It naturally follows that the best way to create and receive kindness is to wear very little armor—to be vulnerable, in other words.

Maybe the best way to capture the nuance of kindness is through the metaphor of the upside-down hedgehog.

Allow me to explain. At one point when my kids were young, they got it into their heads that we should get a hedgehog as a pet. I dutifully did my dad-research and noted the animal’s high risk of getting foot and mouth disease. I then proceeded to watch one short video after the next of hedgehogs floating on their backs in a sink or tub as their owners gently washed their extremely soft undersides.

“Hey, here’s a good life lesson,” I told my kids, sounding, I remember thinking, a lot like my dad. “Try to live life with your belly exposed, and your spines—spines are those prickly, hollow hairs on hedgehogs’ backs—retracted.”

“But won’t people poke a sharp stick in your belly, Daddy?”

“Yes—sometimes. But you take it out and hand it back to those people who do, while looking them directly in the eye and calmly asking, ‘Did you intend to stick that thing in my stomach?’”  

I might have also added, but didn’t in fear of sounding too much like a game integration theorist (which I am not!), Now that you’ve gauged their intent, adjust your next move, and surround yourself with people who don’t mistake your kindness for weakness.

In the end, we decided not to get a hedgehog. But it was hard to forget one of their biggest distinguishing features: Hedgehogs have two distinct sides, one soft, the other forceful. Sort of like kindness.

There is one last—and crucial—element of kindness that became evident to me around this same time. Fundamentally, kindness involves helping other living beings embrace their agency. Think back to how your favorite childhood teacher or coach made you feel. Chances are they saw your potential in ways you couldn’t. They pushed you to see it, too. In return, you did your best for them. You couldn’t bear the idea of disappointing them, but more important—as they likely told you—was you not disappointing yourself. And when you fell short, they forgave you. There was grace.

So, where does math fit into all of this? Well, first, let’s be clear about one thing. Math is a science. It’s the study of structure, order, and relations. It’s not money. It’s not accounting. It’s not the exclusive province of business. It’s not made by humans.

From my perspective, the principles and properties of math are discovered, not invented. To me, math resides in nature. In the phases of the moon, in the tides, in gravity, in hedgehogs, and yes, in kindness. It makes sense that those same Enlightenment philosophers who helped readers discover their agency, which was made possible by concepts like liberty and free markets, spent a lot of time reflecting on kindness as they gave birth to the study of representative democracy and economics.

Human beings desire agency; kindness involves the exchange of agency; and math quantifies the portion of that exchange that can be quantified.

Maybe that’s why I blurted out the words kindness and math during the first town hall meeting I lead with our Ashley Stewart executive team. Amid the chaos, when everyone in the company, including me, was about to be stripped of all surface credentials and civility, only the truth remained. Despite being stuck inside what was a dehumanizing corporate video game, the only—the best—solution was to reestablish some sort of natural order. The words kindness and math came from a deep place. An intuitive place. A human place.

Leading a business with kindness and math, then, is fundamentally about creating a more natural space for the exchange of goods and services among human beings, for human beings. An equilibrium with fewer artificial boxes and constraints, and more and better flow, balance, and thus agility. Because of this, I believe that leading with kindness and math can generate greater value over the long term. More value to stakeholders and more value to society.

Along the way, you might also notice more joy, not just in yourself but in the energy of those around you. It might cause you to pause and remind yourself not to confuse business conventions for the more transcendent truths of life.

Accounting is a helpful reporting integration tool to facilitate comparison between companies, but it is not a true, accurate measure of accountability, a statement about our obligations to others. A conventionally defined balance sheet can never hope to capture the value of the assets present among living, breathing human beings.

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