Sailors and Pirates

Here’s a fun metaphor for you. I’ve been chatting with colleagues about the behavior patterns and habits of leaders that I’ve been observing, and we recognized that there are two loose groups that we can see: sailors and pirates.

The sailors are part of the crew. They are following orders and making things that have been deemed important happen. Ordinary sailors have little agency: they are part of the larger machine that is intent on moving in a certain direction. Sailors higher in the power structure (and there is usually a power structure when sailors get together) have more agency. They have more freedom in how the things happen, but they are still held responsible for whether they happen or not.

Organization leaders who are sailors are subject to the primary anxiety of things being out of control. Their catastrophic scenario is that all this wonderful energy that they have in the people they lead is not applied effectively to the problem at hand. They wake up in cold sweat after dreaming of being lost or late, of being disoriented and bewildered in some chaotic mess. 

This makes them fairly easy to spot. Listen to how they talk. They will nearly always speak of the need to align, to make better decisions, to be more efficient and better coordinated. Sailor leaders love organizing things. For a sailor leader, neat is good.

Every organization needs sailors. Particularly in scenarios where we know where we are going, sailors are who will get you there.  They are the reliable folks who feel pride and honor to drive their particular ship (or part of the ship, no matter how small) toward the destination. Sailor leaders don’t have to be boring, but they prefer it that way. Excitement is best confined to the box where it doesn’t disrupt the forward movement.

Pirates are different. The word “pirate” conjures all kinds of imagery, some vividly negative. For our purposes, let’s take Jack Sparrow as the kind of pirate we’re talking about here.

As I mentioned, pirates are different. They loathe the orderly environment that the sailors thrive in. They yearn for a small ship that can move fast and make unexpected lateral moves.

Pirate’s driving anxiety is that of confinement. Whether consciously or not, their catastrophizing always involves being stuck. Their nightmares are filled with visions of being trapped or restrained, with no possibility of escape, of being pressed down by immovable weight.

Pirates seek options and choose to play in environments where the options are many. This is why we often find them in chaotic environments, though chaos is not something they may seek directly. It’s just that when there’s chaos, many of the variables that were previously thought to be constant become changeable. It’s that space that is opened up by the chaos-induced shifts that the pirates thrive in. And sometimes, often unwittingly, they will keep causing a little chaos – or a lot of it – to create that option space.

Pirate leaders are also not difficult to detect. They are usually the weird ones. They keep resisting the organization’s desire to be organized. They usually shun positions of power and upward movement in the hierarchies. For the saddest pirate is the one who climbed through the ranks to arrive at a highly prestigious, yet extremely sailor position.

Pirate leaders are known to inject chaos. If you’ve ever been to a meticulously planned and organized meeting, where its key participant throws the script away right at the beginning and takes it in a completely different direction – you’ve met a pirate leader.

It’s easy to see how sailors and pirates are oil and water. Sailors despise the pirate’s incessant bucking of the system. Pirates hate the rigid order of the sailors and their desire to reduce the available options. 

Then, why are pirates even found in organizations? Aren’t they better off in their Flying Dutchman somewhere, doing their pirate things?

The thing is, pirates need sailors. A shipful of pirates is not really a ship. With everyone seeking options, the thing ain’t going anywhere. Pirates need sailors who are happy to organize the boring details of the pirate adventure. And the more ambitious the adventure, the more sailors are needed.

Conversely, sailors need pirates. A ship that doesn’t have a single pirate isn’t a ship either – it’s an island. The most organized and neat state of a ship is static equilibrium. When a pirate captain leaves a ship, and no pirate steps up, the ship may look functional for a while, and even look nicer, all of the cannons shining of bright polish and sails finally washed and repaired.

But over time, it will become apparent that the reason for all these excellent looks is the lack of actual action. The safest, neatest course of action is to stay in place and preserve the glorious legends of the past.

The mutual disdain, combined with the mutual need creates a powerful tension. Every team and organization has it. The tension can only be resolved dynamically – what could have been the right proportion of pirates and sailors yesterday might not be the same today. Sometimes we could use fewer pirates, and other times, we need more of them.

To resolve this tension well, organizations need this interesting flexibility, where pirates and sailors aren’t identities, but roles. Especially in leadership, the ability to play both roles well is a valuable skill. Being able to assume the role flexibly depending on the situation gives us the capacity to be both pirates and sailors – and gives the organization a much higher chance of acting in accordance with its intentions.

The most effective pirate is a meta-pirate: someone who can be both a pirate and a sailor in the moment as a way to keep the opportunity space maximally open.

We all have this capacity. The reason I described the nightmare plots for the sailor and the pirate is to help you recognize them in your own dreams. Experienced both kinds? You are likely both a little bit of a pirate and a sailor at heart. If one is more common than the other, that’s probably the indicator of where you are leaning currently. So, if you’re looking to become a meta-pirate, that’s an indicator of where to focus the work of detaching the role from your identity.