Successful CIOs should lead like a pirate captain

By Josef Langerman, Professor of Practice at the University of Johannesburg, and Technology Executive at Standard Bank Group.

Pirates are known for recklessness and raucousness, plundering and pillaging, an unruly gang of cutthroats ruthlessly commanded by a charismatic captain.

This could not be further from the truth. Pirates operated a highly organised criminal enterprise and if we cherrypick there, we can learn a lot from them.

Unlike the swashbuckling pirates we see on the silver screen, the pirates of yesteryear ran a highly sophisticated organisation, possessed great team coordination and possessed leadership and management capability on par with the best modern MBA graduates.

Much of what we know about pirates is simply wrong. In reality, pirate captains were savvy business leaders, who treated their people well, were democratic, and trusted one another.

The first lesson a CIO can learn from a pirate captain is that a pirate captain was primarily a leader and not a manager (the quartermaster played the role of the manager). A pirate captain had to have a compelling vision, as nobody was forced to join a pirate ship.

There had to be something compelling to motivate the recruit to sign on. The recruit had to believe in the vision and have confidence in the captain. Often people don’t just buy into the vision, they also buy into the person.

The questions every CIO should ask themself are: “Do I have a vision that is inspiring?”; and, “Do people buy into me as a person?” Leaders have followers. Do you have willing followers?

Secondly, a pirate captain was not an autocrat. Pirate ships were democratic places. All rules had to be agreed unanimously.

If pirates did not like the captain’s style or how he treated the crew, then he could be “voted off the island”. Since the captain could be fired at any time, he had a vested interested in taking good care of his employees.

Leading a team

A pirate captain behaved far closer to a servant leader than the tyrant we might imagine. In contrast to this, captains in the Royal or Merchant Navy often abused their authority, having crew members flogged or executed, denied rations, and docked pay to maintain control and order.

The question for the savvy CIO here is similar to the previous one: Would your crew vote for you as their leader or would they send you packing?

The only time a pirate captain could pull rank was during a war or a battle. In such time of crisis, there is no time for consensual decision-making. Then the captain had to be decisive, issuing orders that were obeyed without hesitation.

In times of emergency, like we experience with COVID-19, CIOs should step up, get their hands dirty and make the necessary difficult decisions.

Also contrary to popular belief, the pirate captain didn’t have a fancy cabin but slept very much like the crew and ate the same food. The hierarchy was flat. The captain’s wages weren’t significantly larger than the crew’s and the difference between the highest and lowest paid crew members was only a single share.

If you fought bravely or were the first to notice targets then you were handsomely rewarded with bonuses. These villains of the past even had disability plans covering battle-related injuries.

Again the CIO could ask himself if he is rewarding the people who deliver outcomes, or is he rewarding the talkers? Do your business outcomes reflect the effort that people put in and do you reward them accordingly?

A key feature of a pirate ship’s crew was their diversity. For the pirates, racism just wasn’t good business, but treating people right was.

It is estimated that the average pirate ship was approximately 25% black. Most pirates were uneducated and came from the lower classes of society but a few were well educated from higher stations in life.

Each crewmember, regardless of race or social standing, had the right to vote on ship issues and was paid an equal share.

Another aspect of pirating that goes unnoticed is that they were experts at marketing and cultivating a brand.

Pirates knew that fighting was a costly business and did everything in their power not to fight. It just did not make business sense.

They cultivated a fearsome brand, ensuring people surrendered when they saw the Jolly Roger raised. Just that signalling was enough to change the behaviour of the target.

A good question for self-reflection here is: What is your brand and what are you signalling?

Just to be clear, pirates weren’t all goody-two-shoes and our friend Blackbeard was no Robin Hood. They had to cooperate, not so much out of altruism but because it made good business sense. To succeed they needed rules, trust, and an organisational system that was fair.

Their “competition”, the Royal Navy and mercantile ships, were in contrast far more autocratic and workers were exploited to maximise the profit for the captain. Piracy presented an alternative to the way things were done in terms of people management.

Our conclusion then: the pirate business was a people business. The same is true for the pioneers of the digital age.

It is all about people, servant leadership, equality, doing the right thing, rewarding the right outcomes and having a brand that projects a powerful message.

If you are interested in piracy and management have a look at The Invisible Hook: The Hidden Economics of Pirates, or Barking up the Wrong Tree.