Team sports like football, basketball, rugby and hockey require shared understanding and commitment, knowledge, skill and dedication – all of the requirements of a well-run corporation. But there are not too many sporting or business endeavours that require your team to face twenty-metre waves, hundreds of kilometres from shore in isolation.

When he’s not at the helm of Hames Sharley, Managing Director Caillin Howard is in the cockpit of his ocean-going Aikin, an 11.3 metre Kerr yacht that is often seen sliding through southern Australian waters.

Not surprisingly he sees lots of similarities between business and yachting.

“As well as managing a multi-disciplinary design practice I’ve been a cricketer and a sailor,” Caillin says. “So I’ve had some experience in leading a team, dealing with a group of very different people who all have a common goal.

“Purpose, leadership, communication, trust, accountability and commitment are all very important.

“But you learn other unique skills from sailing, such as patience and innovation.

“When it comes to sailing, the first boat to round the weather mark isn’t always the winner. You have to be strategic but also willing to change course depending on the wind direction, the current and what your competitors are doing.

“I remember reading an article in Forbes once which said that sailing – like business – is not about straight lines. Sailors are actually turning away from the wind to create forward velocity, which allows the boat to move faster. It seems like the long way to the finish line, but it’s actually the fastest.

“The article pointed out that in the majority of situations, a straight path is moving directly into the greatest amount of resistance. Sometimes you are better off taking a less obvious route than wasting human, financial and time resources.

“Sailing with the fleet is certainly less risky—you’re not likely to gain or lose your current position. Going the other way is much riskier—depending on which way the wind shifts, you could beat everybody, or you could lose big.

“Risks bring great reward or failure, the key is calculating the value of the risk and when to take it.

“But increasingly in business choosing your own course is often the best path to success.

“We are constantly reassessing our position as a professional services company, as a strategic partner rather than a provider of architectural ‘products’ to our clients. It’s a more holistic offer, a change in the conversation from dollars to value. We’re getting braver to balance and manage our clients’ expectations – it’s about the value we create, which requires time.”

Caillin says ocean-going sailing is a great place to learn about people and the necessary steps managers must take to provide a balance between structure and freedom.

“One of the things I’ve learnt is that there are always a couple of people in the team who need freedom to excel,” Caillin says. “They will flourish in a creative environment where there are very few rules.

“But there are lots of people who crave structure, who need more help and support. It’s a fine line. You obviously want people who are self-enablers, who are not reliant on management to get things done, just like on a yacht you can’t have sailors who lack the confidence to do their job.

“But there also has to be the leaders’ call – in a crisis, someone has to be in charge. It’s a constant balance between providing enough support without shackling growth.”

Caillin relates another story he read last year in Business Insider about the chief operating officer of an international marine company Jonathan Banks, who sailed around the world for four years instead of studying for his MBA.

“I liked the analogy of what you learn at sea being applied to business,” Caillin said.

“For example strategy is very important. As the leader, you need to ensure that everyone on board understands procedures and systems and goals and objectives long before there’s a storm. Vague instructions and misunderstandings can be dangerous.

“Team selection is also important. While in an office environment you can go home at night and let off steam, that’s not a luxury you have on a cramped sailing vessel. Harmony and shared endeavour are very important at sea and in the workplace.

“Staying calm in a crisis is also something you learn when exposed to situations at sea. You have lives depending on you, including your own, and so trusting your decision-making abilities and backing yourself in is very important. When a 50-knot squall hits, everyone needs to shift gears quickly – that’s when training, communication and calm leadership are important.”

A final message that Caillin remembers from reading a piece fellow sailor and CEO of High Brew Coffee, David Smith is it’s important to take time to celebrate success.

“David pointed out that whether you’re on a boat, or building a business, it’s so easy to focus on your destination that by the time you get there, you’ve forgotten all the events and scenery that took place during that process.

“While it’s important to reflect on the past and be prepared for the future, the most important thing about being a dynamic sailor and a successful business leader is to be in the moment.”

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