The Leadership Lessons I Learnt From Niccolo Machiavelli

What I learnt from one of history’s most controversial writers

As I pondered who to ‘learn from’ this week, I decided to go left-field and pick a historical figure who supposedly exemplified ‘bad’ leadership.

Today, the word ‘Machiavellian’ refers to someone, especially a political figure, who is viewed as sly, cunning, unscrupulous and ruthless.

It’s a term rarely used in a complimentary manner and yet, the man behind the expression is regarded as one of history’s most brilliant strategic minds and as “the father of modern political theory.”

Niccolo Machiavelli (1469-1527) was born in Florence, Italy, in a time that saw the country divided into four rival city-states.

Following the French invasion of 1494, Florence’s ruling Medici family fled and, in 1498, Machiavelli became a diplomat within the Florentine Republic.

His political career lasted for 14 years, ending upon the Medici family’s return.

During this time, he developed a reputation for being devious, and was said to exaggerate his underhandedness to shock others.

Having been found to play a part in the unsuccessful attempt to stop the return of the Medici family to Florence, Machiavelli was imprisoned and tortured.


Although he was subsequently pardoned and released, he never again played an active role in politics.

He retreated to his study in 1512 and penned Il Principe (The Prince), which was published posthumously in 1532. Controversial at the time, and equally so in today’s more liberal world, The Prince is essentially a guide on how to rule most effectively as a leader.

His work outlined a number of key ‘leadership’ principles. It’s not possible, argued Machiavelli, to be both a truly effective leader and a kind one.

For a leader to be successful in their ventures, he believed that it’s necessary to be ruthless when it comes to making tough decisions, as this usually means that someone or a group of people will have to suffer for the sake of the greater good.

Other assertions he made include the following:

• Leaders should be feared rather than loved, “if you cannot be both”, in order to avoid a revolt
• Leaders should have the support of the people because it’s difficult to take action without their support
• Leaders should hold good virtues
• Leaders should be intelligent

For Machiavelli, leaders were compelled to deal with the world as it is, rather than how they wished it could be, and this meant that to be naturally kind, considerate and generous could weaken a leader’s position and authority.

It’s important to keep in mind that Machiavelli lived at a time that was politically tumultuous and where countries were ruled more often by the strong than by the wise.

Much of what we find in The Prince is brutal by today’s standards, but it’s a text that’s still studied by leaders all over the world, simply because Machiavelli understood the nature of people.

On his point that if leaders could only be loved or feared, then it was much better to be feared, he added that leaders cannot be feared to the point where people are too afraid.

Such insights made 500 years ago align with today’s research, however. For example, researchers at Stanford University in the United States found that leaders who are assertive or express anger are conferred a higher status and seen to be more competent compared to leaders who come across as reserved or indecisive.

While I cannot concur with everything Machiavelli wrote, we can agree that leadership is tough because human nature is as competitive as it is complex.

And while he might have relaxed his views a little had he been living in the more collaborative world of today, many of the insights he developed during his lifetime are still as relevant today as they were some five centuries ago.

Let’s look at five key insights from Machiavelli’s writings that continue to offer food for thought to business leaders in the 21st Century:

1. Always be present and make yourself available

...if one is on the spot, disorders are seen as they spring up, and one can quickly remedy them; but if one is not at hand, they are heard of only when they are great, and then one can no longer remedy them.

This is great advice for all leaders. We oftentimes tend to get excited about visions of the future and possibilities but all of us need to manage the present. Being present and available enables us to manage today. 

If we don’t manage today well, there will be no point in hoping for tomorrow as it will never become a reality. 

Machiavelli reinforces this point with another quote: “There is such a gap between how one lives and how one should live that he who neglects what is being done for what should be done will learn his destruction rather than his preservation,” urging us to live for today not tomorrow.

2. Learn from others

… to exercise the intellect, the prince should read histories, and study there the actions of illustrious men, to see how they have borne themselves in war, to examine the causes of their victories and defeat, so as to avoid the latter and imitate the former.

Almost 500 years later, Machiavelli’s advice is still sound. Leaders who constantly learn, especially from others, are bound to win.

Are you learning daily? Are you examining others who have tried and gone before you and learning from their mistakes?
If you aren’t, now is a good time to start doing so.

Machiavelli adds: “A prudent man should always follow in the path trodden by great men and imitate those who are most excellent, so that if he does not attain to their greatness, at any rate he will get some tinge of it.”

3. Be prepared for unexpected challenges

A wise prince ought to observe some such rules, and never in peaceful times stand idle, but increase his resources with industry in such a way that they may be available to him in adversity, so that if fortune changes, it may find him prepared to resist her blows.

This is tough advice. Most of the time, when times are good, we bask in them and stop innovating.

Machiavelli advocates working harder in good times to ensure that, when times are tougher, we are prepared.

4. Get constant feedback

There is no other way to guard yourself against flattery than by making men understand that telling you the truth will not offend you.

Most leaders are so isolated from the truth as people are scared to tell it to them.

Machiavelli advocates finding ways to always get feedback and build structures to ensure we are hearing what is really happening on the ground.

The truth may hurt, but only by knowing it will we make the right long-term decisions. Have an inner circle of people who can be totally honest with you about everything.

5. Love those around you

The first method for estimating the intelligence of a ruler is to look at the men he has around him.

Easy to quote but hard to implement. We all say we like to hire people smarter than ourselves, but the reality is different. 

Machiavelli advocates leaders ‘win’ and ‘retain’ smart people with love: “Therefore the best fortress is to be found in the love of the people, for although you may have fortresses, they will not save you if you are hated by the people.”

So, hire great people and surround them with love.

Final thoughts

A final lesson Machiavelli provides me is to never assume someone is bad. I suspect most of us would have labelled Machiavelli an unscrupulous person based on the meaning of the word ‘Machiavellian’ today.


Yet, if we really study him, we find him to be the author of one of the first leadership books in the world, and a very practical leader with a profound worldview.

As we meet different people, although they may come with a bad ‘reputation’ and legacy, never conclude based on another person’s judgment. Make your own call and, just as I was with Machiavelli, you too may be pleasantly surprised.