Today is International Talk Like A Pirate Day, and that gives me an excuse to yet again give everyone the good news about the gay pirates and tell you to watch the delightful show Our Flag Means Death. It reimagines the adventures of the very real life Stede Bonnet (the Gentleman Pirate) when he encounters Edward Teach (Blackbeard) in what I can only describe as a pirate workplace rom-com. I consider this show’s version of Stede Bonnet to be fascinating study in empathetic leadership alongside such greats as Ted Lasso and Jean-Luc Picard. So avast ye, scurvy dog! I present to you: leadership lessons from Our Flag Means Death.
You Don’t Have To Perpetuate Workplace Toxicity
Traditionally, piracy is a culture of abuse… floggings, keelhaulings. And my thought is, “why?” And, “what if it weren’t like that?” (Stede Bonnet, Our Flag Means Death s01e01)
Every workplace has its own suboptimal cultural elements, and some workplaces – and industries – can be far worse than others. It is easy to move up in worlds like this by developing thick skin and becoming successful at enduring it. For underrepresented minorities in such workplaces, we sometimes even make it a point of pride that we succeeded despite the bias, microaggressions, and other cards stacked against us. And left to our own devices, we can find ourselves as leaders teaching other people to endure it like we did, when the better answer is to use the privilege of our seniority to fundamentally change the culture wherever we can. What if your toxic workplace/industry WEREN’T like that?
People Do Their Best When They Feel Secure
If your average pirate doesn’t steal, he doesn’t eat. That’s a lot of mental pressure. So… I pay my crew a salary. Same wage every week, no matter what. (Stede Bonnet, Our Flag Means Death s01e01, but also this is historically accurate for the real Stede Bonnet)
People who are constantly having to worry about surviving don’t have the energy or mental bandwidth for creativity and initiative. This is true when it’s about financial survival and wages, but it’s also true when they worry about layoffs, restructuring, and loss of scope and ownership. Leaders who churn through different goals and organizational structures in rapid succession instead of taking time to make thoughtful decisions end up with teams anxiously anticipating the next big change rather than doing amazing work. Why invest your energy in something your leader might arbitrarily decide to throw out tomorrow?
Brilliant Assholes Aren’t Worth It
Get off my ship. (Stede Bonnet, Our Flag Means Death s01e08)
We’ve all worked with that person. They’re assholes. They’re condescending, they’re self-centered, they lose it when people argue with them, and maybe there’s one or more of bigoted -isms they like to throw in for flavor. Every meeting with them is like walking on eggshells. Everyone finds ways to work around them rather than with them. But, you know, they’re an expert in the field! They have a Reputation ™! They’re so smart!
You don’t need them. They’re doing more harm than good, and they’re probably making the environment so toxic that your up-and-coming Brilliant Nice Person will take their talents elsewhere. Get the brilliant assholes off your ship.
Do The Work To Understand Your Team
A lot of the guys are sweethearts deep down. They’re just dealing with a fair amount of trauma. (Stede Bonnet Our Flag Means Death s01e01)
Most people are not assholes. Conflict on a team and “difficult personalities” are usually not driven by people’s inherent traits; they’re a trauma response informed by past experiences. Maybe that software manager has experience with a previous toxic leader punishing them for taking risks and failing, and that’s why they’re being stubborn about committing to work on a challenging technology program. Maybe that engineer has been stagnant in a role for years being told repeatedly that only a certain kind of work will help them move up the ladder, and what you’re asking them to do doesn’t help that goal. Maybe a team that’s flailing and not making progress has experienced so much churn and redefinition of their charter over the years that they no longer feel comfortable committing to anything. Until you understand what past experiences are informing present behavior, you can’t effectively lead a team through the conflict… and dismissing “people who’ve been hurt before” as actual jerks not worth your time means you’ll never get the chance to see what they can do.
Talk it Through, As A Crew
Stede: Chauncey, sometimes when we get a bit angry, do you know what we like to do? We talk it through.
The Revenge crew, in unison: As a crew! (Our Flag Means Death s01e09)
This is my favorite, as anyone with the misfortune to have worked with me since 2022 will tell you. Talk about things. Give problems names and do it out loud. Acknowledge the bad days and bad experiences and how they affect people’s morale, energy, and focus. I once worked on a team at a company that went through a significant round of layoffs, and while most of our team was safe, many members of partner teams – and close colleagues – lost their jobs without any clear rhyme or reason to who was safe and who wasn’t, and everyone felt shaken. Senior leaders took an attitude of “the show must go on, just buckle down and focus on the work.” In a team meeting I acknowledged what a shitty week we’d all been having and how I knew that meant we wouldn’t be very productive. I had a ton of team members message me privately to thank me for acknowledging it — because not a single other leader had. It doesn’t take much to validate people’s feelings and help a team work through it. You just have to be willing to talk it through… as a crew.
