Captain’s List —Jack Sparrow #882

Corsair’s Profiles in Leadership Series

Decision-First AI
Career Accelerator
Published in
3 min readMay 13, 2016

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The captains of fiction and history have much to teach us. They are leaders who often serve in times of great challenge and turmoil. Articles in this series focus on an individual captain and utilizes their quotes, their writings, and their actions to inspire core leadership elements in all of us.

Captain Jack Sparrow

The iconic, Keith Richards inspired, Captain of the Black Pearl in Disney’s Pirates of the Caribbean franchise is a wealth of quotes and character. He is not your stereotypical leader, but then… Pirate.

Jack is a leader by example and inspiration. A style that can be hit or miss in many situations. But Jack, in typical Tim Gunn fashion, makes it work by adding two important attributes. Two quotes from the original movie capture these nicely and will be our focus for this article.

“What a man can do and what a man can’t do”

Setting expectations is critical, especially for those more inclined to lead by example. Without clear expectations, those we lead will be left to believe they are suppose to model their leader fully. Unless you are in a situation where a handful of clones all doing the exact same things is useful, this will not create an efficient management style.

Jack understood that his companions and crew needed to understand the expectations set for them. More importantly, they needed to accept them. Also critical to Jack’s style, he knew those expectations need to be achievable. Throughout PotC’s swashbuckling storyline, only Jack is really trying to do the unthinkable, his supporting cast is tasked with activities and challenges much more catered to their individual abilities to contribute.

That is not to say that the expectations for Will or Elizabeth or even Mr Gibbs are small. Each member of the team was challenged with a strong dose of adversity and struggle. To help them rise to the occasion, Jack utilized a second tool…

“You will always remember this as the day you almost caught Captain Jack Sparrow”

Inspiration is another strong weapon for lead by example captains. It is especially true when the tasks and challenges of your crew will be uniquely theirs. You need those who follow you to raise their game and what better way than to portray yourself in a memorable, inspiring, and some times larger than life fashion.

Captain Jack is the star of the show. If that inspires others, it will create a powerful amount of leverage for your team and organization. It is a difficult line to walk however. Fame and glory can defeat inspiration if they lead to jealousy or a belief that the mission is only an ego trip. Jake overcomes this by being Jack. For most leaders, I would advise trying to play up the mission, the vision, the fun… acting like a half-mad pirate might be fun, but not likely to endear you to most modern day business situations.

Inspire Song

Follow Jack’s lead in setting reasonable expectations, work to inspire those around you, raise their game, and you might just be rewarded with your own Michael Bolton Half-Mad Pirate Ballad … or at least a shanty…

Corsair’s Profiles in Leadership, Captain’s List is an article format created by Corsair’s Publishing in conjunction with our parent company Corsair’s Ventures. This series seeks to focus the reader on core components of leadership by utilizing the larger-than-life and often fictitious stories of the great captains of history.

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Decision-First AI
Career Accelerator

FKA Corsair's Publishing - Articles that engage, educate, and entertain through analogies, analytics, and … occasionally, pirates!