'Princess Bride' Leadership Lessons


By Matt Schiering

I know I'm not alone in my deep, borderline-obsessive affinity for this classic movie. I've probably watched it fifty times over the years. This past week, Cary Elwes (Westley) made the TV rounds promoting his new book, As You Wish, and it inspired me to pen a short list of leadership lessons that every businessperson can surely take from this great film. I hope you'll enjoy them and tag on your own:

Inigo Montoya: Let's start with singularity of purpose. I mean, is there a clearer (or cooler) mission statement in the history of film? This is who I am, here's what you did, this is what's going down! In one 60-second span, Inigo shares his mission with six-fingered Count Rugen FIVE TIMES. Bottom line: Once you've determined what you're all about, you can effectively bring people with you. While likely the most memorable of Inigo's leadership lessons, I offer two more...

...One of these is encouragement: To Fezzik: "That Vezzini, he can fuss...." (finish it, you know you want to). And then, "Probably, he means no harm..." These are intentional, mood-lifting set-ups for his giant companion. "You have a great gift for rhyme!" is a compliment intended to boost self-esteem - and it does! Bottom line: Effort to make people feel appreciated and the ride will be an enjoyable one. "...Yes, yes, some of the time." (couldn't leave that hanging).

Another is this: Ask for help! Inigo calling upon his deceased father to guide his sword is classic. And it imparts one of the toughest leadership lessons there is; one I struggled with for years. I once believed, wrongly, that requesting assistance from others - subordinates in particular - was a sign of weakness. Of course, it can be among a leader's greatest strengths. It allows people to contribute and it makes them feel valued. Besides, bottom line: together, all of us are always smarter than any single one of us.

Prince Humperdinck: You don't have to be Miracle Max to know that Humperdinck is a poor leader. His two most glaring flaws are arrogance - "If I'm wrong...and I'm never wrong..." and deceitfulness - his four fastest ships never left with Buttercup's letters (whom he was plotting to off on their wedding night for heaven's sake). People catch on quickly if you're lying to them, and no one wants to work for an arrogant stiff, even if said stiff is the smartest person in the room. Bottom line: humility and sensitivity, though demanding greater effort, take you farther....and won't compel you to fight "to the pain!"

Westley: Optimism is thy name! In response to Buttercup's contention that they'll never survive the fire swamp, Westley quickly notes without irony, "Nonsense! You're only saying that because no one ever has!" Better still is the positive manner in which he reassures his beloved they'll survive the three terrors - lightning sand, flame spurts and....well, even though Westley contends R.O.U.S.'s don't exist, he dispatches one with vigor once proven wrong. Bottom line: convince yourself that anything is possible and the odds of doing the impossible (and gaining aid from others) rise dramatically.

Of course optimism only gets you half way. Westley knows this, which is why his leadership also hinges on good planning. I mean, come on..."I'm not left-handed, either?" What foresight! And don't get me started on building up an immunity to iocaine powder just in case you need to win a battle of wits someday. Why, when first confronted with storming the castle (guarded by sixty men!) Westley notes, "Impossible...if I had weeks to plan, maybe..." In fairness, he quickly modifies course once he realizes he has a cloak and wheelbarrow at his disposal. So arguably, planning on-the-fly is also a strong leadership trait. Bottom line: prepare yourself and your team for anything and no matter what comes your way, you'll be confident and ready.

Vezzini: Starting a war requires strong leadership, and in truth, Vezzini almost pulls it off. His ultimate failure underscores two watch-outs for leaders. The first is intimidation: "Did I mention that your JOB is at stake!?" is played for humorous effect. But to threaten a subordinate while that subordinate is literally carrying you up a rope is...unwise. Vezzini's intimidation costs him the loyalty of both his associates. Bottom line: you almost always get more with sugar.

Second, and even more costly is overconfidence. We know that Vezzini's fate is sealed the moment he tells the man in black, "...you're no match for my brain." And, telling people they've fallen prey to one of the classic blunders, before they've actually done so? Inconceivable! Bottom line: confidence is ok, valuable even, but it's a liability the moment you add the prefix "over-" to the root.

Princess Buttercup: "Will you promise not to hurt him?" -- Not one of the best remembered lines in the movie, but a great turning point in the film and a super leadership lesson: Negotiate. The princess knows they're outmatched and trapped after exiting the fire swamp. Contrary to testosterone-fueled Westley ("Death First!"), she knows that the key to longer term victory is surviving the moment. Brains trumps beauty marvelously here and the bottom line is: know when to count your losses, recoup, rise to fight another day.

Grandpa: I've seen Peter Falk in a great many things, but for me, his small role in this movie defines him. And, two of the greatest leadership lessons of all come from his performance therein. Persistence and Reassurance. Young Fred Savage's character doesn't want a thing to do with this story at first (or his Grandpa, for that matter), but the sage old fella is persistent, humoring him along until, without even realizing it, he's vested deeply in the story. And of course, the line we've come to love is also the reassuring last line of the film: "As you wish..." which clearly translates to I love you, kid and I'd do anything to support you. Bottom line: for me, this is what the greatest leaders do - they persist and they reassure. We're in this together and we'll get through this together. Roll credits....

Matt Schiering is Principal at Sheer Strategy since 2017. Sheer Strategy offers a collaborative and dynamic experience designed to uncover key insights, develop and advance strategy and drive results for your organization. From training world-class life science manufacturing sales teams to developing concept to commercialization pathways for government-affiliated agencies, we’ve got you covered. You can reach Matt at mattschiering@optonline.net

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