Finding Your Style As A Leader — Leadership Lessons From “Our Flag Means Death”
Stede Bonnett was not your typical pirate. At a high level, the HBO Max Original featuring Rhys Davie and Taiki Waititi is fairly accurate…
Stede Bonnett was not your typical pirate. At a high level, the HBO Max Original featuring Rhys Davie and Taiki Waititi is fairly accurate from a historical perspective. Once you zoom in, you can see the added flair and comedy that you’d expect from the duo.
Some quick facts that made Stede Bonnet’s captaining style unique (more at the end):
Salaried crew
Extravagant wardrobe
No seafaring experience at all
Stede’s background was as a well-educated, wealthy land-owner. He’d never been on the sea, had no business being a pirate, yet stocked a ten gun sloop with 70 men and left his married life for the Barbadian seas.
While his background leaves him ill-prepared for captaining a seafaring vessel, he’s got the coin to make it happen and employs an experienced crew to set sail to Barbados.
Not giving in to how “it’s always been done”
While Stede Bonnet may not have lasted long as a pirate, he did it his way.
Especially in a new role or new company, it can be easy to try and slide into how things have been done in the past, but that shouldn’t mean you give up your identity.
Our Flag Means Death makes a point to show the crew’s weariness around Stede’s unique style. Stede has no idea how things are normally done, so he does them his way, finding a style that fits his crew.
This means bringing new ideas to the table. In Season 1, Stede forces his crew to go on holiday. The concept of “holiday” is new to everyone (after all, they’ve never been salaried before). So new in fact, that two crewmates practice their hand-to-hand combat because they’re not sure what else to do.
While these new ideas and ways of doing things can be scary for you and your team, innovation pushes the boundaries of expectation and helps everyone grow. Just because it’s only every been done one way doesn’t mean that one way is right.
Let your personality shine
Companies talk about “bringing your whole self to work,” but what does that mean? Your quirks make you who you are, and you shouldn’t have to hide that in your new role.
Stede is likely the first pirate to have a whole library on board his ship, but as a voracious reader, he views a library as essential. His wardrobe is absurd to all others, but he feels most comfortable dressed to the nines and in a powdered wig. Stede exudes personality in all facets of his captainry and is general uncaring to how that is perceived.
As leaders, it’s important to present your personality to your team because it helps with consistency. Your team learns what they can expect from you and it prevents you from forcing behaviors that aren’t natural for yourself.
Make your crew a part of the decision-making
When you yourself have no idea how something should be done, and your crew is aware, it’s helpful to make them a part of the decision-making process. Stede is approached about the lack of a flag on their ship, the Revenge, and has his crew sew some together to see which is best.
While the flags are laughed at when they receive Royal Navy boarders, the crew bands together in support of each others flags. By banding together, I mean they kill most of the Royal Navy members making fun of their flags, but they do so together!
At the end of the episode all flags are raised on the main mast, making all participants feel as though they were a part of the decision-making.
Don’t be someone you’re not
It takes a few episodes for Stede to find his footing, but you start to see his crew take a shine to the more unique aspects of his captainship. In real life and in the show, Stede names his ship “Revenge,” which is intended to seem menacing since Stede has no one to enact revenge upon.
Stede is not scary, he is not tough, he is not ruthless, and he definitely isn’t a stone-cold killer. When episode one concludes, Stede participates in the accidental death of Nigel Badminton, a childhood bully and overall jerkwad. Badminton fell on his own sword when walking out of Stede’s quarters, but two of the crew play it up to make Stede seem as though he had done it intentionally.
While these examples help create mythos to outsiders, those closest to Stede know what’s really going on. Pretending to be someone you’re not is rarely beneficial with your direct team and those you work most closely with will see through the visage.
Final Thoughts
There is much to be learned from televised leaders, and Stede Bonnet is another example of some good and some bad. Terribly equipped to lead a pirate crew, but within the crew itself, they come to appreciate the panache he brings to the sea.
Don’t be afraid to be bold and break the rules that typically bind you to standard leadership practices. Try new things out, especially when it means unveiling more of your personality.
More Stede Bonnet Facts
Pirated from 1717–1718
Historians believe Stede had a “Disorder in his Mind” for wanting to go pirating.
“he was afterwards rather pity’d than condemned, by those that were acquainted with him, believing that this Humour of going a Pyrating, proceeded from a Disorder in his Mind, which had been but too visible in him, some Time before this wicked Understaking.”
He is said to have left for a life of piracy because “some Discomforts he found in a married State.”
Bonnet did meet up with Edward Teach (aka Blackbeard) but their connection was much less mutual. Blackbeard took command of Stede’s crew, casting Stede aside, to the point where Stede contemplated leaving piracy altogether and starting a fresh life in Spain or Portugal.
Stede was hanged with his remaining crew in Charleston, SC on December 10, 1718
From Daniel Defoe’s “A General History of the Pyrates,” originally published in 1724.