The Art of Disappointing People

Are you a Classical Leader, Or a Modern Manager?

When I first stepped into the role of headmaster—years ago now, when I still had a twinkle in mine eye—I had an older gentleman take me aside and ask, “What’s the definition of leadership?” Knowing that this was a loaded question (and that he was eager to tell me the answer), I said I didn’t know. He looked me in the eyes and said, “Disappointing people at the rate that they can handle.” Then he laughed in a way that was not entirely encouraging, and I took it as a somewhat shallow and cynical view. Surely leadership was different. Surely leadership was respectable. All the popular books have told us so.

But after six months of meetings with parents, faculty, board members—meetings that never really felt like “wins” but sometimes more like pyrrhic victories—I reckoned there was no small amount of wisdom in that statement. I put my hand over my mouth. The old gentlemen was a prophet and a sage.

In the classical world, a good leader is one who knows how to communicate their vision of the Good in such a way that moves people to do the right thing—even if the truth may at first come as a disappointment. This portrait of the leader stands at odds with the managerial class of corporate leadership science with which we are so often presented today. It’s no accident, for instance, that ex-Navy SEALs have found such great reception in sharing their battlefield lessons in podcasts and books (see Jocko Wilink’s Extreme Ownership). Their popularity is proof that we are searching for something better. And as it turns out, the better things are often the older ones.

Consider a famous passage from Virgil:

As, when in tumults rise th’ ignoble crowd,
Mad are their motions, and their tongues are loud;
And stones and brands in rattling volleys fly,
And all the rustic arms that fury can supply:
If then some grave and pious man appear,
They hush their noise, and lend a list’ning ear;
He soothes with sober words their angry mood,
And quenches their innate desire of blood:
So, when the Father of the Flood appears,
And o’er the seas his sov’reign trident rears,
Their fury falls: he skims the liquid plains,
High on his chariot, and, with loosen’d reins,
Majestic moves along, and awful peace maintains.
(Aeneid, Book I, Dryden translation)

The passage is sometimes used an example of why leaders must have rhetorical mastery, or how persuasive language might serve the sophisticated statesman. But such readings misinterpret the true nature (and classical meaning) of leadership.

The key lies in the little word “pious.” For the classical world, leadership was not simply a fancy trick of clever words but a matter of someone’s “quality”—Cicero’s Latin word for Plato’s Greek “what-ness” (poiotēs). In other words, a leader had something about him that was also reflected in his words, which were ultimately reflected in God’s Reality.

In a modern secular world, words are utilitarian, to be worked like levers in a mechanistic and material world without ultimate meaning. The modern leader uses them. He does not become them, does not exemplify or become the icon of them. Perhaps we lack Homer’s “wingéd words” today. We are told that our words simply go out in war against other words, and that underneath all our rhetorical tricks lies the ancient violence of Hesiod, where we words clash upon some contestable and windswept plain, empty of meaning, having drifted in a no-man’s land, outside the ordered walls of the Real.

In the world God has made, however, words have meaning because they participate in Reality. There are implications of this as a leader. The tradition of magnanimous statesmanship, rooted in the substantive goods of virtue and truth, means that the leader will approach language differently. The classical (and medieval) ideals are inconvenient and uncomfortable but also higher and more noble. And they surpasses the mechanistic and utilitarian leadership models of the corporate world, which are often malleable. So how did the “grave and pious man” calm the rabble? By the weight of his character and the power of his virtue (pietas), not by sophistry or mere cunning.

After Leadership

Alasdaire MacIntyre sounds the warning of this shift away from the classical meaning of leadership in his work After Virtue. He critiques modern moral philosophy, arguing that “emotivism—the framework that views moral judgments are mere expressions of preference—stems from the collapse of a shared ethical tradition and that we must recover that tradition if we to return to the good life. He argues that leaders in bureaucratic systems often lack the virtues needed to cultivate genuine community, and instead prioritize efficiency or power. This is opposed to what Aristotle commends as practical reason.

Cue Michael Scott and the “Peter Principle.” Laurence J. Peter coined this term, stating that in hierarchical organizations, individuals rise to their “level of incompetence”—they are promoted based on performance in their current role until they reach a position where they are no longer competent, leading to ineffective leadership or management. This is essentially the animating principle in hit series The Office (both the American version, as well as the British originator). The Peter Principle suggests that individuals promoted beyond their competence often lack the judgment—Aristotle’s phronesis—required for complex leadership roles. The character of Michael Scott is an example of this phenomenon. Spoiler alert for those living under rocks, Michael is actually a very good salesman, though obviously a terrible boss.

On a more serious note, consider the way in which many handled the COVID situation. Mary Harrington’s First Things article, “The King and The Swarm,” provides some interesting cultural examples: “Briefly ascendant during the COVID crisis, it mobilizes digital ‘representation’ toward a maximally emergent-seeming political order, while evacuating human leadership into purportedly neutral proceduralism wherever possible.” Proceduralism: a blind following of processes and protocols, in spite of how it might contradict our direct experience. COVID proved the point that MacIntyre’s analysis of the modern problem with what happens “After Virtue” is really a just another way of expressing the breakdown that we would see “After Leadership.”

What does this mean for us? It means those who lead classical Christian schools can be tempted to look to the modern managerial corporate class for direction, which often locates the secret to success in instrumental and procedural goods (efficiency, systems, financial prudence). But the older way locates the success of an organization in substantive goods (moral excellence, real culture and conviction, competence), which are situated in the classical Christian tradition. This calls to mind categories with which we should all be familiar.

In Aristotle’s Metaphysics, he discusses four “causes.” (If you are not already familiar with these categories, it’s time you become so.) There are four causes of things:

1. Material Cause: the substance or matter that makes up a thing (e.g., the bronze of a statue).

2. Formal Cause: the essence or structure that defines what a thing is (e.g., the shape or design of the statue).

3. Efficient Cause: The agent or process that brings a thing into being (e.g., the sculptor who crafts the statue).

4. Final Cause: The purpose or end goal for which a thing exists (e.g., the statue’s purpose to honor a deity).

In addition to the causes, uncle Aristotle isn’t silent about what qualities make for a good leader. In his work Nicomachean Ethics, for instance, Aristotle defines magnanimity as the virtue of the great-souled human who pursues honor through noble deeds and good habits and for all community’s sake. Cicero, in De Officiis, emphasizes statesmanship as a duty to justice and public welfare, citing Scipio Africanus’s selfless leadership. Augustine, in City of God, contrasts worldly ambition with leadership guided by divine love, advocating rulers who serve humbly (Book V, 24). St. Thomas says that the virtue of a good man includes also that of a good ruler, because it belongs to a good man both to rule well and to obey well (Q 47.11). A just king, he says, promotes the common good—remember that? you know, the peace, justice, and the flourishing of the community—drawing from Aristotle’s idea that humans are political animals. He contrasts this with unjust rule, where the tyrannous ruler prioritizes personal gain.

Disappointing People

Apply Aristotle’s matrix to the industry of leadership science and to corporate structures. Organizations can either define their success according to material and efficient causes (often what the modern corporate culture does), or they can locate their success in formal and final causes, fulfilling their purpose, even if their revenue is comparatively low. But even this division is a kind of false dichotomy. The causes do not need to be mutually exclusive. Is it possible to harmonize all causes, though knowing how we struggle in this fallen world, it is difficult. As it relates to the success of a classical Christian school (and how that success relates to its leader), I think it’s important to see the hierarchy of goods here. This is what the managerial culture seems to miss. We talk of “mission drift,” but that drift depends upon whatever the mission is and how it is defined. If the “mission” is limited to efficient and material causes, then hitting all your revenue projections or enrollment numbers my not have drift at all—while you have scoffers as students or degenerate behavior concealed beneath sports trophies. Perhaps you are actually hitting your metrics spot on.

If, however, “mission” is rooted in higher and more substantive causes, then enrollment numbers, donor advancement, or even test scores won’t misguide the leader or the school. We see this basic economy of goods even in our Lord’s understanding of commandments, that it may be possible, for instance, to “tithe mint and cumin,” while also to omit “the weightier matters of the law: justice, mercy, and faith.” After all, what if a leader gain the whole world, making his classical Christian school wealthy and academically competitive, but lose its soul? The soul of the institution is connected to the soul of its highest steward. Again, one doesn’t want to have to choose. But alas. Would you rather be established in the classical tradition of leadership, or would you rather just aim for the easier and more modern, therapeutic, and more comfortable visions of leadership?

Final note. Let’s return to our opening question in light of the classical tradition. Let’s acknowledge that a good leader must be able to “disappoint people at the rate that they can handle.” But it is the manner and reason, the how and why of it, that matters. Modern leadership is often conflict-averse, seeking to avoid confrontation altogether and often preferring technocratic means of handling a range of performance issues. Classical statesmanship, however, is not conflict-averse. It seeks more than merely finding the right tools to motivate people or negotiating situations with clever hacks. It is about personal responsibility and wisdom, which Seneca says is the only truly liberal art. It may disappoint people in the short term, but it is always oriented towards the goal of their human excellence, not their machine-like compliance. This vision of leadership is kingly and correlates to God’s own authority, who, by His nature and character, orders all things according to his divine logic. This is the vision we need. Without the right (leadership) vision, the people perish (Prov. 29:18). Or they simply quit.