The Other Machiavelli: Finding lessons for leaders in a lesser-known work by the Florentine political philosopher


However cynical it may seem, Machiavelli’s The Prince has long been recognized as a source of insights for anyone trying run a business or gain power in one. A ferocious little treatise of under 100 pages, The Prince was aimed at Lorenzo de’ Medici, the iron-handed Florentine ruler, by an author hoping to regain the proximity to power that he formerly enjoyed.

But modern corporations aren’t principalities ruled by autocrats. They are, in fact, more like republics, their leaders dependent on the support of directors, employees, customers, investors, and one another. That is why, in turning to Machiavelli for management wisdom, we would be well served to leave aside The Prince in favor of another of his works, one that is less known but perhaps more to the point. Don’t be fooled by the academic-sounding title; Discourses on Livy has a great deal to teach us about leadership in any organization resembling a republic. Chances are, that includes your business.

Published posthumously in 1531, Discourses draws on the ancient Roman historian (among others) to analyze the nature of power in public life. Like The Prince, this is not a handbook for saints. But the author was a brilliant student of human nature, and not one to underestimate the potential of a determined individual. In Discourses, he firmly asserts the importance of an individual founder in establishing or renovating a republic—and by extension, for our purposes, a business. A prudent founder, he writes, “must strive to assume sole authority.”

Yet a single person cannot sustain an enterprise in the long run. That is only possible if the founder’s vision and talents result in an institution supported by stakeholders who can carry the venture into the future. “Kingdoms which depend only upon the exceptional ability of a single man are not long enduring,” Machiavelli writes, “because such talent disappears with the life of the man, and rarely does it happen to be restored in his successor.”

Besides, princes have no monopoly on wisdom. Despite the notorious unpredictability of the mob, the author acknowledged the wisdom of crowds when he asserted that “the multitude is wiser and more constant than a prince.” Machiavelli was also insightful about succession: “After an excellent prince, a weak prince can maintain himself,” he observed with admirable economy in one chapter’s epigraph, “but after a weak prince, no kingdom can be maintained with another weak one.”

Many of the epigraphs are bull’s-eyes of this kind. Take this one, for example: “Whoever wishes to reform a long-established state in a free city should retain at least the appearance of its ancient ways.” This is worth doing even if you make massive changes, because, Machiavelli notes, “men in general live as much by appearances as by realities; indeed, they are often moved more by things as they appear than by things as they really are.”

Honesty may be the best policy, but that is not a maxim ever attributed to Machiavelli. In keeping with the notion that people attend largely to appearances, he says leaders compelled to do something by necessity should consider pretending their course of action was undertaken out of generosity. In another chapter, he argues, “Cunning and deceit will serve a man better than force to rise from a base condition to great fortune.”

Machiavelli, of course, took a hard-headed view of humanity, believing that people act largely out of self-interest, whether to gratify their egos or sate their desire for material wealth, and that, for better or worse, actions tend to be judged by their consequences. Indeed, he was very much what philosophers call a consequentialist, arguing that, in some contexts, bad things must be done to achieve good ends achievable in no other way. This is not to say that law-breaking or other unethical acts are justified—even some of Machiavelli’s contemporaries considered such advice controversial—but every business leader knows that hard decisions must be made, be it the closing of a venerable division or taking a company in a risky new direction, for the long-term good of the enterprise.

Even when advocating something like mercy, Machiavelli did so with consequences in mind. He argued, for example, that failure should not be harshly punished, especially if it arises from ignorance rather than malice. Roman generals, he notes, had difficult and dangerous jobs, and Rome understood that if military leaders had to worry about “examples of Roman commanders who had been crucified or otherwise put to death when they had lost a day’s battles, it would be impossible for that commander, beset by so many suspicions, to make courageous decisions.”

If punishment should not be meted out lightly, neither should rewards be delayed. If you don’t cultivate loyalty and support from others in good times through open-handedness, Machiavelli says, those people certainly won’t have your back when things get rough. Doling out rewards only in the face of tough competition or harsh circumstances will lead subordinates to believe “that they gained this favour not from you but from your adversaries, and since they must fear that after the danger has passed you will take back from them what you have been forced to give them, they will feel no obligation to you whatsoever.”

Republics, in his view, have no choice but to grow, for “it is impossible for a republic to succeed in standing still.” Companies are the same. But acquisitions—whether in battle or by purchase—must be carried out with care, for “conquests made by republics which are not well organized, and which do not proceed according to Roman standards of excellence, bring about their ruin rather than their glorification.”

Finally, Machiavelli was well aware of the risks of advice-giving, so much so that he gave one chapter the title “Of the danger of being prominent in counselling any enterprise, and how that danger increases with the importance of such enterprise.” Consultants, take note. Just don’t let the clients catch you reading Machiavelli.

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