Leadership Lessons from Robin Hood That Still Apply to Modern Day

Share this Page
Share on facebook
Share on twitter
Share on pinterest
Share on reddit
Share on whatsapp
Share on email
Share on facebook

Every holiday season my husband and I read a book aloud to one another. This years first pick? The Adventures of Robin Hood by Roger Lancelyn Green. As we read through those 336 pages, I realized that Robin Hood had some important leadership lessons to teach us. Leadership lessons that, though they’re part of a centuries old legend, still apply to modern day.

#1 Seek Out Challenges

Robin Hood is not a man who runs from a challenge, instead he seeks them out. Often, he starts them himself. He understands that a successful leader must prove himself, time and time again, by putting his skills to the test. These acts serve not just as a testament to the group you lead, your burgeoning partnerships, and (of course) your adversaries, but also to yourself. Every good leader should question his skills. He should live a life that dares him to do better.

What are you best at? Robin Hood is undoubtedly best at bow and arrow. Certainly we could spend a paragraph or two together, creating a list of similes, obvious comparisons, and brief allegories which could explain how your “bow and arrow” might translate to a modern skill, but I’m confident you get the idea.

Find what you’re best at. Do you already know it as your eyes scan across this sentence? Write it down. Draw a line underneath it. Ask yourself how you can put your skills to the test.

#2 Surround Yourself with Your Betters

Perhaps what is most surprising about Robin Hood is the way he makes friends and gains followers. It goes like this: Robin meets a man in the road and challenges him. The man, if he is a man of honor, will accept the challenge. The two men will throw about insults that can only be found in fifteenth century, after which they come to physical blows.

Oftentimes, the man challenged will be a coward or a liar. They aim to cheat, they fight poorly, they lack honor. In turn, Robin takes what he can from them (robbing them of their gold for the sake of his cause) and sends them ashamedly on their way.

However, now and again Robin will meet a fair match. This challenger will get in a few good blows with fist or staff. If they’re truly skilled, they will be one of the few men to knock Robin down, to cause him a fair amount of bruising and cost him a good amount of blood. At the end of these fights, Robin will be bleeding, wounded, flat on his face, ass on the ground. And what does he do? He smiles.

When Robin is bested he sees something in this experience that a lesser man would miss. He has just met a man that can match him, blow for blow. It’s these skilled men that Robin offers a place at his side, whose hands he shakes proudly, whose shoulders he throws a friendly arm around. Seeing the type of man Robin is, these challengers can never decline him. He may have lost the physical fight, but by losing he has gained something far greater.

Can you say honestly that those closest to you are your betters? Make accomplices out of those who better you. Learn to make allies out of those who challenge you and win.

#3 Know What You Stand For

The adventures of Robin Hood may be many and varied, but they all have the same true aim: to fight for the rightful return of King Richard to his throne. Robin knows what he stands for and he knows what he stands against. There are no ifs, ands, or buts about it. The goal is clear, it is noble, and it is above himself as an individual. He fights for something greater than himself and his own successes. Any good leader, whether a businessman, entrepreneur, or manager, should know what he stands for at his core.

Be clear about your overall goal. Not just to write it down as your mission statement on the back of a promotional flyer, but so you have a true guide for what you do, day in and day out. Leadership is no easy task. In fact, that’s why you’re reading this right now. But when you know what you stand for? The path gets a whole lot clearer.

To know your core purpose, in whatever leadership endeavor you pursue, is important for several reasons. First, it acts to set your own compass. Any true leader knows that guidance is something he must set for himself. Without knowing your aim, how can you possibly set a course? Secondly, it sets a trajectory for those who come with you on the journey. Set your course, pave the way honorably, and in turn make those that follow proud to be a part of the grand design you’ve set forward.

#4 The Role of Those Above is to Serve Those Below (Not the other way around…)

There is some confusion in pop culture about the methods by which Robin Hood reached his goals and why. The words, “steal from the rich and give to poor,” mark many a turned phrase when it comes to this legend. It’s true that this phrase may leave you to believe that Robin Hood was an anarchist. In reality, his message was the opposite.

Robin Hood believed in the purity of hierarchical systems, an inherent structure that successful business depends on every single day. He didn’t fight against the concept of leadership. Instead, he encouraged separation by skill, merit, and ability. The entirety of his workings were to return King Richard, the rightful king, to power. It wasn’t the monarchy he was fighting, it was the misuse of it.

Robin, like many chivalrous men of the past, understood something about leadership that many in the modern world are keen to forget: the role of those above is to serve those below—not the other way around.

And so, I must introduce you to legend of Robin Hood’s ultimate nemesis: King John. What was so wrong with King John anyway? If you were to ask Robin Hood, he’d have quite a lot to say in answer. In its simplest explanation, King John manipulated the very systems which were set in place to protect those at its lowest tier. In a system designed (at least in its purest sense) to provide for not only for its top tiers but its bottom tiers as well, King John took advantage. He overthrew the balance. His job as King was to provide safety and security to all his people, instead he tipped the scales in favor of himself and of the traitorous noble class that showed him loyalty. To a man like Robin Hood (and the rightful King he fought for), these acts could be described with only a few choice words, the first of which is pure evil. Robin Hood fought to restore that balance with what he believed to be a rightful and fair king, one that served his people (and not the other way around).

The second half of this lesson is of just as much import and it is this: servitude of your followers is not about servitude to you as an individual. Rather, it is about servitude to the greater goal. In the case of Robin Hood and King Richard, their goal was to create a success out of a land and out of a people in a society doing its best to thrive. In your case, it might mean creating a successful business out of serving others nobly with your skills and abilities so that they in turn may find their success.

A leader who takes advantage of those who serve beneath him by turning the balance inward, seeking benefit only for his own desires, is no leader at all.  He is a tyrant. Instead, lead nobly and with honor. Know the true nature of your role and fulfill it humbly. Don’t be a King John. Be a King Richard. Be a Robin Hood.

#5 You Head the Battle

When danger is afoot, Robin Hood never allows his followers to fly first into battle. Instead, it is Robin who carries the greatest risk. As it should be for any great leader. His followers love him well enough to gladly offer their sacrifice, but Robin never accepts a sacrifice on his behalf, only a sacrifice for the greater goals in which he believes.

Those you lead must trust in the security and the safety you offer. It is you who must show the greatest bravery and hold the greatest risk so that those behind you may feel inspired to do the same. 


We often forget that fiction can hold our greatest truths. The next time you find yourself reading a hero story, see what lessons you can pull from it. 

Suggested Posts for You to Read Next:

10 Inspirational Books to Reset Your Life

UnF*ck Yourself Book Review | A Personal Development Book by Gary John Bishop

Share This Post
Share on facebook
Share on twitter
Share on pinterest
Share on reddit
Share on whatsapp
Share on email
Share on facebook
Bex Skoog

Bex Skoog

Bex Skoog is the creator of the 'Out of the Bex' website, a guide to a more thoughtful life through books and simple living. If she had three wishes they would be for teacups to never empty, to possess an unending supply of classic films, and have access to the world's greatest libraries. Bex lives in Virginia outside of Washington D.C. with her husband and hundreds of stray books.

Join Our Mailing List

Join the Out of the Bex community.

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.