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7 conceivable leadership lessons from The Princess Bride

I recently had a few unexpected moments alone to wander through a bookstore where I discovered an adult coloring book commemorating the 30th anniversary of The Princess Bride, a cult classic released in 1987. Since this is my favorite film, I of course had to purchase the coloring book. It may seem inconceivable to glean relevant leadership lessons from a 30-year-old movie. However, it is one of the most quoted movies of all time, and according to Chris Sarandon who played Prince Humperdink, it’s eternal and multi-generational. Fans of the movie are known for their ability to quote nearly every line, and after 30 years of loving this movie and making a living in the business world, I can pull leadership lessons from nearly all those lines. Unless you’re unemployed in Greenland, no one has time to dissect every piece of dialogue. Therefore, I’ve narrowed it down to seven leadership lessons from some of my favorite lines. 

“As you wish.” – Farm Boy

In the beginning of the movie viewers are introduced to Farm Boy and Buttercup. Farm Boy does Buttercup’s every bidding while only speaking three words, “as you wish.” Granted, he is employed by Buttercup’s family and it’s kind of his job to do what she asks, but eventually she figures out his three little words are secret code for “I love you.” Because of this love, he has a desire to serve her, causing him to willingly perform every task immediately. Farm Boy, who we later learn is named Westley, demonstrates servant leadership. At first, he appears to be the subordinate heeding Buttercup’s every beck and call. Very quickly, however, we see him as a leader set on bettering himself to better serve his true love. 

“Servant leadership is a paradox – an approach to leadership that runs counter to common sense,” says Peter Northouse, author of Leadership Theory and Practice. Servant leaders put others first and help empower and encourage them to reach their full potential. We saw early signs of servant leadership in Westley’s service to Buttercup on the farm. This style of leadership becomes more evident once he connects with Inigo and Fezzik. Northouse stated servant leadership works best when leaders are altruistic, honest and fair with their followers, develop strong long-term relationships with their followers, and have strong motivation. Westley was an ethical person who showed respect even for his enemies. He developed friendships with those enemies and helped them meet their goals through his leadership. He was strongly motivated by true love and an inner sense of altruism. Through his acts of servant leadership, he brought two lost and lonely followers together, befriended them, helped them formulate and execute a plan that met all their needs, defeated an evil prince, and rescued his one true love.

Lesson learned: Have a servant’s heart.

“You keep using that word. I do not think it means what you think it means.” – Inigo Montoya

The Sicilian Vizzini repeatedly exclaims, “inconceivable!” He only says it six times, but they are all close together and contextually incorrect, leading Inigo Montoya, the revenge-focused Spaniard, to determine Vizzini doesn’t really know what the word means. During 14 years in non-profit management I heard the word “transparency” a lot more than six times. After the first several times I heard a constituent cry for transparency, I started hearing Mandy Patinkin’s voice in my head repeating, “You keep using that word. I do not think it means what you think it means.” 

According to Peter Barron Stark, transparency is consistently behaving in a predictable manner. It is best for leaders to be honest, act with integrity, keep their followers and those to whom they answer informed and maintain a consistent message.  If for some reason a leader cannot answer a question or provide requested data, they should openly tell the requester why they are not able to fulfill their request. Members of the non-profit organizations for which I worked thought they had a right to know whatever they wanted, regardless of confidentiality and common business practices. They thought transparency meant they had a right to know staff salaries or who dissented on a board of director’s vote. As part of her leadership classes, Dynamic Directions President Adorna Carroll strongly states members of a board or association have a right to know what decisions have been made on their behalf, but they do not have a right to know every detail of how that decision was made. 

The American people and many journalists cry out for transparency from our government citing the people’s right to know. However, they misjudge or misunderstand the seriousness of this demand. Some information could get people killed if it was made public. That’s why we have confidentiality and security levels. Rather than demanding our leaders tell us everything, we should seek consistency. As leaders, we should lead consistently and keep people as informed as confidentiality allows.

Lesson learned: Transparency is not the same as full disclosure.

“I’ve got my country’s 500th anniversary to plan, my wedding to arrange, my wife to murder and Guilder to frame for it; I’m swamped.” – Prince Humperdink

This scene leaves me doubled over in laughter because I completely relate to it (the being swamped part, not the murder and framing part). Count Rugen and Prince Humperdink are wrapping up a meeting outside the secret tree entrance to the pit of despair when Count Rugen asks if the prince would like to come down and watch him torture Westley. Humperdink makes the whole scene so casual and normal, just two buds chatting, when he says, “Tyrone, you know how much I love watching you work.” He then rattles off his to-do list, shrugs his shoulders, and says, “I’m swamped.” Rugan totally understands, and like any good friend, encourages Humperdink to get some rest. 

How many times as a leader have you turned a friend down because you were too swamped? As leaders, we often must say no to good things so we can prioritize the better things. Whether it’s watching a friend at work, a meeting that could just be an email update or a project that could be delegated, leaders need to keep their priorities in mind and learn to say no to create enough margin to accomplish the truly important and have a little extra time for rest. After all, if you haven’t got your health, what do you have?

Lesson learned: Maintain your priorities.

“Any word from Westley?” – Princess Buttercup

Buttercup thinks Westley has returned to his ship as the Dread Pirate Roberts, but Humperdink knows he’s really in the pit of despair strapped to Count Tyrone Rugen’s table enduring experimental torture. Despite this knowledge, Prince Humperdink promises Buttercup he will send his four fastest ships to find Westley. Periodically, she pops into Humperdink’s rooms to ask if he’s heard from Westley. Each time she unknowingly interrupts a meeting concerning part of Humperdink’s plans to murder her on their wedding day.

The leadership lesson Buttercup should have learned, but fortunately we’re able to understand, is it’s good to follow up, but make sure you’re paying enough attention to discern what’s really going on. Buttercup was so consumed with issues concerning her own heart (Westley coming for her) that she was oblivious to the subterfuge going on all around her. 

Lesson learned: Stay informed and be discerning.

“Have fun storming the castle!” – Miracle Max

Leadership, according to Northouse, is “a process whereby an individual influences a group of individuals to achieve a common goal.” This process involves accountability, dealing with a variety of personalities, obstacles and demanding work. After sending Inigo, Fezzik and Westley off with a miracle pill to bring Westley back to life, Miracle Max shouts, “have fun storming the castle!” The phrase has evolved into a sarcastic statement used to describe well wishes to someone heading off into drudgery or something that will be difficult and not at all fun. The Urban Dictionary uses the following example: One person says they’re heading to work, their friend says, “have fun storming the castle.”

There may be moments or even entire days or weeks in leadership that feel like storming the castle. Just as Miracle Max suggested, leaders can find joy in the arduous work. They can have fun despite fighting against seemingly insurmountable odds. When it’s just your brains, someone else’s brawn, and another’s steel against 60 of the Prince’s men, you may be tempted to run back to the thieves’ forest and hide. But if you can find joy in the journey, you can have fun storming the castle. 

Lesson learned: Find joy amidst hard things.

“He’s been mostly dead all day.” – Fezzik

Inigo and Fezzik carry Westley to the wall outside the palace and give him the pill from Miracle Max. Almost immediately Westley responds. When he moves his finger, Fezzik praises his achievement. Westley brushes aside the encouragement, stating he’s always been a quick healer. Fezzik stays positive and continues pointing out and praising Westley’s advancements. When challenged about his celebration of seemingly meaningless things, Fezzik reminds both Westley and Inigo that Westley has been mostly dead all day. Considering Westley’s near-death experience, Fezzik thinks he deserves some grace and encouragement. Westley and Inigo, however, are focused on formulating a plan to rescue Buttercup and allow Inigo to confront Count Rugen. They think Fezzik is slowing them down by interrupting with encouragement, but Fezzik is unphased and continues his positive attitude.

Both servant leaders and transformational leaders build relationships with others and honor them as full human beings. They listen and show empathy. Fezzik exemplifies these leadership qualities by noticing and celebrating the small milestones in Westley’s recovery. Even when we’re distracted, we all need encouragement. So as leaders, it’s important that we both give and receive encouragement and extend a little grace to our colleagues who may have been mostly dead all day.

Lesson learned: Encourage others and celebrate the small victories.

“My name is Inigo Montoya. You killed my father. Prepare to die.” – Inigo Montoya

Perhaps the most well-known quote from The Princess Bride and most repeated in the movie comes from Inigo when he calmly and deliberately says, “Hello. My name is Inigo Montoya. You killed my father. Prepare to die.” We first hear him say it atop the Cliffs of Insanity after fighting with the Man in Black. They call the fight a draw and Inigo tells Westley how he came to be such an outstanding swordsman. His passion for avenging his father’s death drove him to become an expert in swordplay. The fencing expertise is a means to finding and killing the six-fingered man who murdered his father and both physically and emotionally scarred Inigo for life. Once he encounters Rugan, he says the words he had practiced for 20 years. Rugan stabs him in the gut and thinks he has won. It looks like Inigo is about to give up, but he finds strength to continue by repeating the long-rehearsed phrase. At first, he speaks weakly, but with each repetition his strength increases until he shouts out the words and eventually defeats his father’s killer.

While I wouldn’t encourage living a purpose driven life based on revenge, I do think we can learn from Inigo’s passion. Inigo had one driving passion that defined everything he did. When he wanted to quit, he reminded himself why he was pushing so hard. He had a mantra and he repeated it whenever he needed inspiration. Do you know your why? Leaders know the organization and its mission and help guide and encourage followers to reach common goals. If you don’t know the mission or have a passion that drives you toward that goal, how can you inspire others to bring the plan to fruition? 

Lesson learned: Know your purpose and gain strength from it.


The storyline of The Princess Bride and all its glorious quotes that have become part of pop culture has many examples of both good and bad leadership. Forcing innocent young women into marriage only to murder them and start a war – bad leadership. Defeating your good-hearted enemies, sparing their lives, transforming them into friends and rescuing the princess – good leadership. Most of us don’t fight these types of battles in our everyday leadership, but unlike Vizzini and the inconceivable idea he might not be the smartest guy in Floren, we can learn valuable leadership lessons while enjoying a good laugh. Besides, studies show humor is one of the keys to success. 


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