Machiavelli is one of those historical figures whom everyone has heard of, but few know everything about. Born in 1469 in Florence, Italy, at the height of the Renaissance, Niccolὸ Machiavelli may be best known as a political strategist and author, but he was also a politician. The Prince, his most famous book, is a handbook on how to rule well in Renaissance Europe (which also includes helpful tips on how not to get overthrown or assassinated). It might have been one of those texts you had to read in school, but even if you’re not schooled in 15th century humanism, his name probably rings a bell because his surname is widely used as an adjective. If someone behaves in a Machiavellian way, they are “cunning, scheming and unscrupulous, especially in politics.” Frank Underwood in House of Cards? Machiavellian. Certain U.S. politicians who shall go unnamed? Machiavellian.

This definition is not entirely fair, because Machiavelli himself was no cartoonish puppet-master. He was a thoughtful, funny philosopher who only began writing after a long career in politics, after he was ousted, perhaps even out-Machiavellied, by his rivals. He held a leading role in Florence during one of the periods when the ruling Medici family had been expelled from the city. Once they returned to power, he was persona non grata and, therefore, took up the pen in his retirement. The Prince, published in 1515, was dedicated to the new Medici leader, Lorenzo, and intended to be a guide to good leadership. But that’s where Machiavelli’s negative reputation, largely unearned, comes in. The Prince enjoyed centuries of popularity because the lessons in it, the most famous of which is “it’s better to be feared than loved,” were seen as teaching wily, immoral, even despotic behavior, which all made for exciting reading. In truth, Machiavelli’s ideas are more complex and less two-dimensional than most folks believe. But everyone agrees that he was a brilliant strategist, whose advice and lessons would not only be relevant in a Game of Thrones-like world of cloaked intrigue, among the Borgias and their like, but also would be applicable to everyday life today, particularly for leaders, politicians, and CEOs.

In order to best understand how to be Machiavellian today (in a good sense), we spoke to Christopher Celenza, a leading expert in 15th century Italian humanism and author of a new biography, Machiavelli: A Portrait, published by Harvard University Press. Celenza is a professor at Johns Hopkins University and was recently director of the American Academy of Rome.

He offers five tips, drawn from Machiavelli’s life and writings, which would be at home in any good manual for leaders across the centuries, whether one’s a duke living in 1515 or a COO in 2015.

Surround yourself with smart people who tell it like it is. No one is helped if you’re surrounded by “yes-men” and flatterers. Whether you’re making decisions for a company with millions in the balance, or choosing what to wear to the prom, you want advice from intelligent people who will not only be respectful but who will also tell you the truth.

It is better to be respected than loved. That’s a slight variation on what Machiavelli wrote, but for leaders and CEOs, these days being “feared” is not much of a motivator for workers. You want to inspire respect and perhaps instill in them the fear of disappointing you (the chances of staff being beheaded is much lower than it was circa 1515). “Machiavelli says that, in an ideal world, a leader would be both feared and loved,” Celenza says. “But in truth, if you had to choose, it’s better to be feared, because that’s something you can control by your actions.” Even doling out bonuses and vacations is no guarantee of being loved—that’s an emotion largely beyond your control. Being loved by your staff is nice, but it’s important to keep enough of a distance so that you’ll be respected, and they will want to do a good job in order to not disappoint you. Hope for bonuses has thankfully replaced fear of losing body parts, but the general idea of the lesson remains.

Predict potential problems. Avoid hubris and anticipate the good and the bad that might take place in the future. “Machiavelli often talks about leaders,” Celenza continues, “and one attribute that he loves is when leaders can see into the future, they look ahead. He says the ancient Romans were great because they looked ahead to problems and tried to head them off at the pass. It’s the ancient virtue of prudence: looking ahead and seeing what potential problems might be.” Like a chess player, look several moves ahead and prepare responses to a variety of possibilities.

Don’t put everything on your shoulders. “Machiavelli believes that real leaders in institutions are the ones who depend only on themselves. They build an institution that can survive them,” Celenza says. True leaders don’t make everything depend on them, but delegate to people they trust, and build an institutional culture that will go on even when they’ve retired (or been overthrown in a military coup, depending on your century). Whether it’s a Renaissance dynasty that must survive the death of its prince, or a company like Apple that must soldier on post-Steve Jobs, the best leaders prepare accordingly, knowing that work must be done, and the company must continue, even without them.

Have a sense of humor about yourself—it’s a good defense against enemies. Machiavelli was a funny guy who wrote comic plays, and had an overall comic sensibility. His letters to friends are full of dirty jokes, and he saw humor in the craziness of the world. He also undermined potential nay-sayers, the Internet trolls of the Renaissance, by making fun of himself. In his old age, he was smitten with a courtesan, yet he still published a play about an old man who falls for a beautiful young woman even though he probably shouldn’t have.

Many of these points sound similar to those mentioned in a new book called Work Rules! by Google’s head of HR, Laszlo Bock. If Machiavelli were alive today, it’s a good bet that he’d be working for, or maybe even running, Google.

Click here to see Rose’s tips for healthy and happy relationships

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