Machiavellian Leadership and Knowing Yourself to Lead Yourself: DeMarco Banter

I’ve been spending the last few years reading some of the classic philosophers.  One I keep coming back to is Machiavelli. Over the next few weeks we will dive into the works of Machiavelli from a DeMarconian angle. We all know—context matters. Given the context of Machiavelli’s writings—is it possible he is a bit misunderstood?  I mean how would you respond if Cesare Borgia invited you to dinner?


Consider who Cesare Borgia was—he was the quintessential bad boy of the Renaissance. Borgia was the illegitimate son of Pope Alexander VI, Borgia ravaged northern Italy, seizing towns and murdering those who stood in his way. Not even his allies were safe. A Borgia dinner invite could be a death sentence. He stabbed, strangled and poisoned with impunity.

Cesare Borgia was killed in 1507, so Borgia dinner invites are hard to come by these days—but the his spirit lives on in some of the terrible leaders we see day in and day out.  If we have not run into a Borgia leader yet—we will all meet a Cesare Borgia type at some point.

He–or she–will probably not be obvious at first. A new manager, a work colleague, a community leader, maybe even a pastor–it doesn’t matter which disguise the Borgia leader wears—but before we meet our Borgia leader, we must be prepared.

Who better to advise us than someone who met the original Borgia leader and lived to write about it? As a Florentine diplomat, Niccolò Machiavelli spent four months in Borgia’s court. The behavior Machiavelli witnessed inspired his work—The Prince.

I totally understand—at first glance, The Prince may seem irrelevant to our present day. After all, the piece is 500 years old. But abuse of power is not unique to Renaissance politics. It can occur at any time, in any workplace, in any relationship. The principles Machiavelli discovered apply equally to our lives today when read in a particular light.

In popular culture, Machiavelli is synonymous with deceit and treachery. If one were to Google Machiavellian—we would find the definition: “cunning, scheming, and unscrupulous, especially in politics or in advancing one’s career.”  However, Machiavelli’s main concerns really dealt with the stability of the state and the welfare of its people. Much of his leadership advice is common sense. In Chapter 21 of The Prince, Machiavelli explains what leaders must do to be esteemed. Leaders who hold Christmas parties, Presidents who attend the Olympics and CEOs who act as philanthropists are simply following his counsel.

Philanthropy, of course, is far less interesting than murder. While Machiavelli admired Borgia, he also recognized Borgia‘s weaknesses.  Machiavelli identifies some unpalatable truths about human nature and gives them to his readers straight. If we refuse to acknowledge these truths, we become easy prey for the first Borgia leader to happen our way. Powerful people do not always play nice.

These days, of course, leaders are a bit less bloodthirsty than Borgia. If we cross our commander or manager, s/he probably won’t have someone drowned in the Tiber. Backstabbing is just not what it used to be; typically there’s no funeral involved.

Even so, misjudging a relationship with a powerful Borgia leader can jeopardize a career, health and a bank account balance. Just check your news feed and you’ll find stories of leaders who abused their power and with each story we need to ponder their victims.

Power is most often abused when both the perpetrator and the victim share a dysfunctional beliefs about power. Both act out of fear. The perpetrator fears losing power, or being exposed as a fraud. The victim fears humiliation and ridicule. In the end, both reap what they fear most.

The sad fact is very few people actually know how to lead. This was as true during the Renaissance as it is today.  Good (educated) Leaders channel the energies of their people toward a common goal. They temper their self-interest. They build networks, rather than fortresses.  It’s sad, but most people lack these skills. Instead, they cajole, criticize or threaten—what we might call fear, sarcasm, and ridicule. This is not leadership; this is just bullying. It is the only strategy Borgia leaders know.

Bullies are essentially weak. We all learned the best defense against a bully in grammar school—but it’s hard.  The secret is not to cringe, nor to fight back. The best defense against a bully is no defense at all. Bullies are not attracted to people who are strong, calm and self-confident.  This is exactly what Machiavelli was driving at  in The Prince.

We will all be tested by bullies—any decent bully knows how to press our buttons. We all suffer from self-doubts, and bullies sense these instinctively. If we cower, we become victims. If we fight back aggressively, we become the bullies. Neither stance will bring us happiness. Once we begin bullying others, we must always watch our backs. The vast majority of Roman Emperors cited in The Prince died violently, before their time. Every time we bully someone, we create an enemy.

How we respond to those more powerful than us shapes our treatment of those who are weaker. We will all be given the opportunity to lead others. It might be at work, in politics, in our community, or even within our family. Families can be the most dangerous of all–Cesare Borgia is said to have murdered his brother. Those whom we know intimately are best attuned to our frailties.  Family know our weaknesses, wrinkles, and flaws.

When we become leaders, we will be challenged. If we have any self-doubts, they will become obvious to others. We all have strengths and weaknesses. If we try to hide our weaknesses, they will be exposed.  Self-awareness is a huge key to leadership—leading from our strengths and hiring for our weaknesses.

The key to effective leadership is self-awareness and self-acceptance. This is not what most people imagine when they think of Machiavelli. But men like Borgia were destroyed precisely because they lacked self-awareness. Had Borgia recognized his weaknesses, he would have taken a different path. But only strong leaders can acknowledge their weaknesses and compensate.

Self-acceptance is equally important. Once we accept our imperfections, they lose their power and others cannot use them to manipulate us. We find the courage needed to speak the truth to power. And we find it easier to accept imperfections in others. Whether we lead or follow, self-awarness and self-acceptance are indispensable.

machiavelliMachiavelli teaches us to take responsibility for our relationship with power. This is not obligatory, of course, but merely wise. Understanding Machiavelli gives us a richer appreciation for human nature. It allows us to foresee problems, defuse dangerous situations and make wiser decisions.

To learn the inner workings of power, pick up The Prince. Observe others with unfailing honesty—speak truth to power. Look within yourself. Identify and acknowledge your weaknesses. Cultivate your inner strengths. Then, when the Borgia leader in your life invites you to dinner, you will be able to respond with clarity and confidence.

Some of the concepts and ideas in this post were borrowed from several sources to include a myriad internet sources as well as an article in Forbes Magazine—Why Machiavelli Matters, 24 Sept 2008.

3 Replies to “Machiavellian Leadership and Knowing Yourself to Lead Yourself: DeMarco Banter”

  1. “Philanthropy, of course, is far less interesting than a good old-fashioned murder.” Bill, great piece, made me chuckle… and ponder… and reflect. Thanks for sharing. I always learn from your insights so look forward to reading your piece when it is ready.

  2. Awesome read boss. Hopefully the Niners can apply some Machiavellian principles to the upcoming season and bring one home!

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