What Philosophy Can Teach You About Being a Better Leader summary

What makes life meaningful and enjoyable? For thousands of years, that’s been one of the central questions of philosophy. 

The ancient Greek philosopher Aristotle believed that the answer lies with our ability to reason. In his view, we become self-actualized human beings by making rational choices based on what we think is right and wrong. This is what makes us different from animals, who live just to survive, or slaves, who have been stripped of their freedom to make choices. 

How often do you hear phrases like “It’s a dog-eat-dog world,” or “If I don’t look out for myself, no one will”? Behind these phrases is a philosophical perspective that we’re all on one-person teams, competing with each other.

A famous business simulation exercise illustrates how deeply ingrained this perspective is. In the experiment, participants are gathered into groups, and each group is given a pretend fishing company to run. Members have to design the ideal strategy for their company, and adapt that strategy as obstacles are introduced. 

There are right ways and wrong ways to do many things in life, like following a recipe, putting air in your tires, or weeding your garden. But in competitive activities like sports and business, there’s no single “right way” to play. 

That means that while we can learn from the mistakes and successes of others, competitive activities aren’t about following set steps. Instead, we should think about them as a playing field with some rules in place, and a bunch of people coming up with creative ways to try to win. Think about a professional basketball team competing in the NBA. In one scenario, its members might focus their strategy on getting their point guard to shoot as many threes as possible. In another scenario, the best strategy might be running out the clock, or double-teaming a star player on the other team. There’s no single secret to how to win. 

Imagine you’re applying for jobs, and two firms are interested in hiring you. You meet the CEO of each of them. One CEO is late to the meeting, interrupts you, and yells at his secretary. The second CEO listens respectfully, is honest with you about the responsibilities of your position, and asks for your insight into solving a problem. Which boss would you rather work for?

Chances are, you’d much prefer the second boss. That’s because the first boss has fallen prey to a common misconception about leadership. Often, leaders feel they need to assert their power visibly in order to come across as legitimate leaders. But in reality, the opposite is often true. This principle goes all the way back to Ancient Rome, where the philosopher Plutarch argued that the best way to influence others isn’t through control, but by example. 

It's easy to think that authority means having all the power in the room. But real authority actually does the opposite: it works hard to make everyone feel empowered.  

One of the biggest mistakes we make is to think about empowerment as something to be “granted” rather than something to “gain.” When leaders treat power as a resource to bestow in certain quantities on those below them, their workers are not actually being empowered. That’s just “granting” something temporarily. 

How often do you experience the feeling of going ‘round and ‘round in a discussion without actually getting anywhere?

This can happen because we think we’re listening when, often, we really aren’t. In reality, we have entered the conversation with a set opinion and a predetermined outcome. Even if we claim we’re open to new ideas, a lot of the time, we’re actually trying to control a conversation. 

You know that feeling of excitement and inspiration, when what you’re working on doesn’t even feel like work anymore? Maybe you’re thinking, “Yeah, I experience that about once every five years.” Well, feeling that way is what it means to be engaged, and it turns out that being engaged isn’t some magic formula – it’s actually a baseline human condition. 

Unfortunately, a lot of company culture has the whole idea of engagement backward. Management thinks of engagement as something that needs to be created. But if being engaged is how we naturally are, then the problem lies elsewhere. 

Every day, leaders need to make dozens of decisions. One hopes that that decision-making is guided by a sense of morality and a desire to do what is right. If the world were cleanly divided between “right” and “wrong,” that wouldn’t be so hard. Unfortunately, that’s not how the world works. What makes ethical decision-making so difficult is that the real dilemma isn’t about choosing between right and wrong, but about choosing between two competing “rights.”

Take the following story, which occurred at the height of World War Two. An Allied officer received word that there had been a leak of very important information by a member of his staff. He tried his best to find out which of his secretaries had leaked it, but to no avail. Eventually, he had to choose between two “rights.” If he fired all of the secretaries, he would ensure there would be no more leaks, which would protect the lives of soldiers. If he fired no one, he would ensure no innocent secretary would be punished for the wrongdoing of another. There wasn’t a clear right or wrong. Instead, he had to weigh the relative value of each “right” against the other. 

It’s easy to think about freedom as power. By that logic, when we’re free, we’re free to do whatever we want. But in actuality, freedom involves a lot of responsibility. 

Think about the following scenario. Mario has been tasked with designing the new website for his company, and he has been given instructions for every single component, from the colors to the banner design. His job is that of a designer, but in reality, he doesn’t actually have any freedom to design. Without freedom, Mario probably feels held back, bored, and disempowered.