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6 Leadership Lessons from the Dread Pirate Roberts

Ahoy, matey! Beware the ship flying the Jolly Roger, for ’tis the Dread Pirate Roberts who captains it, and he takes no prisoners if ye choose to resist!

Here are the six strategic leadership lessons modeled by the Dread Pirate Roberts:

  1. Set and measure personal goals
  2. Align your business goals with your personal goals
  3. Build your personal brand
  4. Seek out and motivate new talent
  5. Create a succession plan
  6. Have a Contingency Plan in Place

The Princess Bride fared only so-so in the theaters when it was released in 1987, but thanks to video tapes and DVDs, it has made it on the “Top 100” lists of several film organizations: Top 100 Greatest Love StoriesTop 101 ScreenplaysReaders Picks Top 100 Movies, and Rotten Tomatoes Top 100 Comedy Movies, to name a few.

Leadership Lessons from Dread Pirate Roberts

In spite of its mediocre debut, the Princess Bride endures in American culture because of its classic story line, the unique characters, and, most of all, its quotability. There is one particular character from whom we, as organizational change and leadership consultants can learn much: The Dread Pirate Roberts.

Let’s take a deeper look at the six lessons of leadership we can learn from the Dread Pirate Roberts:

Set and measure personal goals

The Dread Pirate Roberts knew what he wanted out of life since his teenage years. He was deeply in love with Buttercup. His personal hopes kept him alive during the most difficult of trials as a pirate prisoner.

Align your business goals with your personal goals

Oddly enough, we do not see the Dread Pirate Roberts on his ship during the movie. He sails a small boat in pursuit of the captors of his true love, but after that, he spends the entire movie amongst land lubbers.

The Dread Pirate Roberts 4.0 (Wesley) was making a great living on the high seas, had achieved a dream leadership position and enjoyed both fame and fortune. Still, he was willing to leave it all in order to pursue his personal goals and fulfill his personal promise to the one he loved. Business leaders who lose sight of their personal goals, who focus solely on their business development and success, are likely to find that such success, once achieved, is hollow. Life balance is critical to a satisfying career.

Build your personal brand

When Princess Buttercup met Wesley as the Man in Black, she knew almost immediately who he was. He came by sea, was an excellent swordsman, was strong, and displayed cunning sufficient to survive a duel of wits to the death. Plus, he dressed the part! Business leaders who build their own personal brand can often enjoy similar rewards of recognition. Consider the following successful leaders:

Richard Branson: known for his adventurous spirit (think round-the-world ballooning and cross-Atlantic speed boating), his trademark goatee and long blonde hair, and his efforts to constantly challenge the status quo in established industries (airlines, hotels, publishing).

Warren Buffett: The Oracle of Omaha has built his success on his personal brand of honesty (e.g. acknowledging shortcomings at annual shareholder meetings), humility (the third richest man in the world still buys his own egg McMuffin for breakfast), and hands-off leadership.

Donald Trump: Love him or hate him (there seems to be very little in between), there is no denying that Donald Trump knows how to cultivate his personal brand: direct, brash and arrogant with a hairdo that is unmistakable in a crowd.

What can you do to create a brand? Dress the part.
How about legendary football coaches Don Shula with his trademark hat and Paul “Bear” Bryant with his sports coat and matching hat. Do you have your own favorite hat? Favorite color? A scarf? Identify your personality through your brand so others can recognize you in a crowd.

Seek out and motivate new talent

Without a pipeline of up and coming talent, a leader’s goal of succession will remain out of reach. The Dread Pirate Roberts understood the role of cultivating new talent to help him achieve his own goals: “Good night, Wesley. Good work. Sleep well. I’ll most likely kill you in the morning.” After years of motivating Wesley to develop fencing and leadership skills, the captain had found his successor.

Create a succession plan

Wesley was, according to his story, already the fourth in the successful leadership line of Dread Pirate Roberts: Roberts, Cummerbund, Ryan and Wesley. Building a plan not only to pass the baton, the ship’s leadership had established both traditions and tactics to create trust in the next leader. Without the support of the former leader, the success of the new leader is much less likely. Additionally, the retiring captain was willing to take a back seat to the new captain and give him his full support.

Implement contingency plans

Battling Vizzini as the Dread Pirate Roberts, Wesley administered poison to both his competition and himself. Once Vizzoni was dead, Wesley explained to the princess, “I spent the last few years building up an immunity to iocane powder.”

What are you doing as a leader to make your business immune to the economic, political, cultural and commercial poisons that would otherwise be the death of both your organization and your competitors?

Next time you get the urge to say, “Hello, my name is Inigo Montoya. You killed me father. Prepare to die,” listen carefully for more leadership lessons from one of the most feared movie pirates of all time. You’ll find several more. It’s not inconceivable.

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