Pirates in the boardroom

Back to insights

Do you have a pirate in the boardroom? Or do you need a pirate in the boardroom?

I’m not talking about Pirates as caricatures, like Jack Sparrow, or criminals who attack at sea to plunder ships in today’s seas. Traditional pirates were interesting individuals who started to fix what they viewed as tyrannical – battling against endless prejudice in the pursuit of equality. 

You may think that a pirate in your boardroom would lead to chaos, rebellion, and untold peril. I want to show you that inviting Will Turner into your boardroom could be the single act to secure your future success.

Join me back in the golden age of piracy

Between 1650 and 1720, thousands of pirates were actively breaking the rules and changing the world – people like Bartholomew Roberts and Edward Teach, aka ‘Blackbeard’. In many ways, their world was very different to ours:

  • Following the Spanish War of Succession, two-thirds of the Royal Navy was redundant.
  • Public execution was a popular form of entertainment.
  • Pre-school children were sent to work up the chimneys and down the mines.
  • Slavery was accepted as a good investment opportunity.
  • And women were viewed as second-class citizens.

And yet, in some ways, our worlds are not too dissimilar because we also face untold pressures. We are about to venture into the uncharted waters of a recession under the leadership of a new Prime Minister and a new King. And we are still coming off the back of a pandemic, which accelerated digital transformation, led to the great resignation, and global supply chain instability.

world mop

Pirates succeeded because they created productive discomfort

Pirates had the right level of rebellion, agitated people for the right reasons, and challenged the right things – like long-held beliefs – to encourage new thinking. 

In his book, ‘Be More Pirate‘, Sam Conniff distills success in the golden age of piracy as:

  • Rebel: drew strength by standing up to the status quo. 
  • Rewrite: bent, broke but most importantly rewrote the rules. 
  • Reorganise: collaborated to achieve scale, rather than growth. 
  • Redistribute: fought for fairness, to share power, and make an enemy of exploitation. 
  • Retell: weaponised their story – and told the hell out of it!

Modern day pirates

While there may have been a golden age of piracy, there are still modern day pirates:

  • Mary Barra of General Motors is the first woman to lead a major carmaker, releasing the world’s first sub-$40,000 electric vehicle to the market (ahead of Tesla!) and one of two global businesses to eliminate the gender pay gap. 
  • Elon Musk has continually pushed boundaries with his entrepreneurship. In Space X he dared to question why they would buy rocket parts when they could manufacture them at 2% of the cost, and make them reusable. Today Nasa outsources contracts to Space X. 
  • Fellow spaceman Richard Branson has built one of the world’s largest and most recognisable brands, challenging the status quo in sectors that span health to hospitality, travel, entertainment, and finance.

The boardroom is often a hostile environment and the one place you really need a pirate. 

There are too many ‘safe’ boards out there that continue to do what’s always been done, which prepares their business for the past rather than the future. It is the most risky strategy going because boards could blindly follow the status quo.

Change is the only constant and you can’t remain blind to it. Only you can secure your future. You need a leader who is brave, courageous and self-confident. A leader who is curious and open to experimenting with new ideas. A leader who will question assumptions and challenge the status quo. 

three men sitting while using laptops and watching man beside whiteboard

You need a pirate on board – someone to create good trouble

Pirates are the perfect role models. Through productive discomfort, they ignited change at the fringes of society, which eventually rocked it to its core to produce transformational change: 

  • Universal suffrage ensured everyone on board was treated equally – something society achieved 240 years after pirates when women were granted voting rights.
  • Injured pirates were paid compensation depending on their injury and assigned alternative duties that matched their ability – society enacted this 200 years later.
  • Everyone was paid fairly and shared the proceeds from their onshore activities.
  • Pirates employed flat hierarchies – a Captain with responsibility for strategy, and an equal Quartermaster to represent the voice of the crew.
  • The Pirate Code provided governance that ensured crew members were held to account.
  • Free from the constraints of society, pirates were able to innovate, experiment, and create new ways of working.

Pirates didn’t set out to start battles, and they didn’t set out to change THE world – only THEIR world. And you can do the same.

I witnessed a great example of this with one of our financial services clients, when the board invited a new person in to run their transformation efforts. He clearly had new ideas and an innovative way of doing things, but rather than go in all guns blazing, he challenged in a respectful way. By agitating people just enough, he encouraged them to think differently and release their grip on their long-held beliefs. 

He created ‘good trouble’ because he knew that unless he agitated the board from the inside, someone would do it from the outside, which would disrupt the business.

The client had to embark on a tender process for a contract renewal with the Bank of England. When it first won the contract 15-years previously it was up against two competitors. This time round it was 42 – and not all of those were direct fintech competitors, many were technology companies with the capabilities to move into the financial services market. When the existing competitors don’t quite meet the needs of the market, pirates emerge to explore alternatives – think challenger brands that completely revolutionise entire sectors. 

Inviting a pirate to the board enabled our client to overcome corporate blindness from a strategy point of view, and see the new world in which it operated. 

Need a first mate?!

S&S was born as a rebellion to transformation failure and outdated consulting models. We help our clients correct this alarming trend and successfully bridge the gap between investment and value realisation. Our engagement philosophy is intentionally simple and lightweight to ensure our people have the freedom to deliver the right outcome for you, so your business is prepared for the Future of Work.

Discover more about The S&S Way

AJ Circle Crop
Written by Adrian Stalham
Read more from the author