Seven Things Sailing Taught Me About Leadership

Don’t complain about the wind. Trim the sails!

The Automated Insurer | Insurance Leadership

By Mike de Waal | 6 July 2022

Key Points

Most entrepreneurs don’t just want to be entrepreneurs—they have to be entrepreneurs.

As a driven entrepreneur, you will encounter challenges and rewards far beyond the average employee’s. Navigating these ups and downs can be as challenging as steering a ship through a storm on the high seas, but I’ve done both—and lived to tell it can be done.

The lessons I learned sailing the seas have served me just as well on land. Here are seven tips about entrepreneurship that sailing has taught me:

1. Know the terminology

In sailing, understanding boating terms like aft, starboard, and leeward is vital to working with your crew and operating your vessel. The same is true in business. If you can’t speak the language of your clients and your competition, your next deal may get lost in mistranslation.

Attending conferences and taking courses are both great ways to learn new terms and highlight that there’s a reason why you’re the expert.

2. Know the destination

The captain and crew must know the final destination when sailing. Without a final destination, the team won’t know where the ship is going, and you’ll risk getting lost at sea. 

Similarly, a business leader must have a vision of what their business is all about: what it does, how it serves its stakeholders, and where it is going. Moreover, a business leader must articulate this vision to inspire the team to work together towards a common goal.

3. Use trends like the wind

When sailing, jibing and tacking help you manipulate the winds to steer your vessel in the right direction. In business, trends are your winds and you need to understand which direction they’re heading in. Take a few minutes daily and bring yourself up to speed on the latest global and local trends.

Aggregators like Feedly or SmartNews, along with social media feeds, keep you on the cutting edge and aware of which way the wind is blowing.

4. Learn when to tighten or ease the sheet

The sheet is a line or rope used to adjust a sail against a force of wind. In business, you need to consider when to tighten or loosen your budget and your business’ growth in line with your sales cycle and market forces.

Markets ebb and flow and your business will, too. Tracking these fluctuations over time will help inform the ideal time to launch marketing campaigns and hire new employees or tighten the purse strings.

5. Adjust quickly and wisely to a changing climate

The weather can change instantly when you’re sailing, and you need to know how to use the sails to compensate, navigate under harsh conditions, and capitalize on whatever is thrown at you. It’s not much different when you’re a business leader.

Like the weather, business is constantly moving and changing. Whether you’re steering your ship at sea or driving your business on land, it takes experience and, at times, raw courage to weather the storm. So, see each storm as a chance to gain experience for the next one and know that sometimes you simply need to batten down the hatches – and wait it out.

6. Take care of your crew

As captain, you must take care of your crew and ensure there’s adequate food, water, sunscreen, and other resources. Additionally, it’s the captain’s responsibility to intervene if crew members create a toxic environment or make others feel uncomfortable. 

Just like in business, leaders must maintain a safe and secure work environment, treat everyone with respect and dignity, create an atmosphere of empowerment and creativity to build confidence and self-esteem, and permit them to grow in a way that gives meaning and purpose to their lives.

Whether in business or sailing, leaders must value each member as someone who keeps the boat sailing toward its intended objective and the overall mission for success.

7. Be a decisive captain

It can take an entire crew to run a sailboat, but they won’t work effectively without a captain calling the shots. The crew relies on your vision, tenacity, and experience to guide their actions. Without this direction, no one will know which way to travel.

As the captain of a ship or a business, you spend your days adjusting your sails, guiding the crew, and navigating dangerous waters. 

8. Surprise

Yes, I said seven things… but as a sailor, there is always a surprise or two thrown in. In February 2020, I was to be part of a multi-hull race crew and we were practising a few miles off St. Maarten when our catamaran de-masted. Fortunately, no one was injured but we had a critical situation that none of us had experienced before. We ensured all were safe, came together, dragged the mast and the sails back on board, and limped back to port to sail another day. I got home and a couple of months later we learned of COVID and the pandemic and changed how we did business. Be prepared for surprises.

So, if you’re on the verge of starting a new business or taking it in a new direction – always keep your hand on the helm and remember:

The pessimist complains about the wind. The optimist expects it to change. The leader trims the sails and sets a new course.

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Mike de Waal

Mike de Waal is president and founder of Global IQX, an Ottawa-based software provider of AI-driven sales and service solutions to employee benefits insurers.  He has deep experience in both software development and business management skills. Early in his career, he worked as a computer programmer and then went on to become a financial planner and a benefits consultant with giant Manulife Financial before becoming a tech entrepreneur.  He can be reached at [email protected].