Lessons on Leadership from the 2017 Race to Mackinac Island

What does a grueling 53-hour sailing race and the daily challenges of building a digital company have in common? Actually, quite a bit.

The Race to Mackinac is a the longest fresh-water sailing race in the world. Starting at Navy Pier in Chicago, it extends 333 miles north to Mackinac Island in upper Michigan.

Begun in 1898 by five sailing friends, it has continued every year since. This year, its 109th, attracted 300 boats of every size and type.

In 2013 I received an invitation from the Chicago Yacht Club to enter Jasmin, my 40-foot Dufour, in the race. This was a dream come true; as a sport, the race is extremely competitive. For a pure encounter with the beauty and fury of nature over the course of 2-3 days, it is hard to beat.

The 2017 Race was particularly special, and not just because we won first place in our racing class! As I reflect on the experience, there emerges several insights that are relevant to my daily adventure as an entrepreneur and CEO.

The Team

There are always a few days over the summer when the considerations are perfect - 1-3 foot waves, 10-15 knot winds - when I’ll take out Jasmin singlehanded. At forty feet, she provides just the right amount of challenge and pleasure while enjoying the beautiful skyline of Chicago.

But in a competitive race like the Mac, I would never attempt to go it alone.

From experience, we have found that for this race, a crew of seven is optimal. We have a shift schedule of watch captains and crew that allows for smooth overlaps and handoffs of work. It’s a team-based approach that is efficient and productive.

To support our racing strategy, we have a clear organizational design that plays to the individual strengths of our crew.

When we have Jasmin up on a 30-degree heel, slicing through the waves on a close reach, there is a real experience of “flow” as a team. Everyone is alert, communicating constantly as we trim the sails for subtle changes in the wind. Every increase in speed, even if it's a tenth of a knot, is celebrated.

This year, two of our seven team members had never sailed on Jasmin before. They were both experienced sailors, but were new to our team. So on-boarding them to our structure, workflow and racing strategy was important. This included our approach to safety, communication and accountability.

There’s nothing like sailing in heavy seas and wind to test the team culture. Stress will always surface issues of professionalism, attitude and communication. Fortunately for us, we had a great team. By the end of the 53-hour race, everyone felt they had known each other for years!

In a company, team culture has a similar impact on the long-term success or failure of the business. Trying to run a business singlehandedly will not scale, and hiring just for skill and not for attitude will not last for long. Defining the strategy, setting expectations, and building a healthy team culture are basics for winning.

The Plan

Like Mike Tyson once said, everyone has a plan until they get punched in the mouth. In a race, you bring the best weather forecast you can get, an intimate knowledge of your boat and your crew, and a set of experiences and intuition to build a race strategy.

And then you meet the wind and the water.

This year, we decided to follow the wind directly across the lake to the Michigan shore. We sailed right past the rhumb line (marking the most direct path). We bet that the wind would eventually move in a counterclockwise direction and allow us to then sail north up the lake. The plan worked, and it wasn’t long before we were leading the entire cruising class.

We continued to follow the wind north and soon crossed back across the rhumb line, taking us farther west than we needed. This was another big gamble. We hoped it would set us up to go over the top of the Manitou Islands instead of taking the shorter but trickier path through the pass between the Islands and the Sleeping Bear Dunes.

Over the Islands or the short-cut through the channel is always a major tactical decision.

At the decision point, I huddled down below in the cabin with Jon and Todd, the other two watch captains, to make the final decision. We decided to go above the Islands. We put our hands together to memorialize this decision.

Then 45 minutes later the wind changed, and we changed our minds to go through the pass! This last-minute change in direction locked in our leadership position in the race.

The lesson? Committing to a plan is important. But being willing to quickly pivot when conditions change is just as important. Never let ego blind you from the reality of the situation.

The Technology

Just like in business, technology has become integral to competitive sailing. The latest in lightweight composite racing sales, satellite downloads of up-to-date weather conditions, and computer modeling to evaluate course corrections are all required to be competitive.

With technology, we can track our competitors even if they aren’t within sight on the horizon. Real-time data analytics have become critical tools on a long-distance race, and we know the other boats are making their own strategic bets based on their interpretations of the weather forecasts and wind direction.

As important as data and technology is, however, leadership still requires thoughtfulness and good judgement. Like in the business world, data analysis will provide important insight, but it takes strategic thinking to apply the insight to the current conditions in the real world.

The Reality

 If you haven't sailed a long-distance race, it’s difficult to appreciate the thrill, the hard work, the competitiveness, and sometime the sheer boredom of the experience. The reality is all this and more.

There are times when you are heeled over, tethered to the boat, trying to keep her on a heading. You are on the edge of fear and ecstasy. Down below, those who are on break may be trying to sleep (good luck with that), prepping a sail, making a repair, or brewing a pot of fresh coffee for the crew above.

When it’s tense, everyone plays their positions. When the conditions relax a bit, then crew members may experiment and try on different roles, learning new positions.

My favorite shift is the middle of the night when the breeze is steady, the crew is hushed, and we are surrounded by darkness. You find yourself staring up the beautiful star field, the splash of the Milky Way, sometimes if you’re lucky, even the Aurora Borealis. It’s spectacular.

Wind is the life blood of sailing. Like sales in business, without a steady source of breeze, you don't move forward. There's nothing worse than bobbing motionless on a blistering, hot July afternoon.

Actually there is one thing worse. Bobbing motionless while staring at the distant horizon and noticing a competitor passing you by. Somehow, by skill or pure luck, your competitor has filled their sails and is leaving you behind. 

When the going gets tough, the tough get creative. By carefully nursing the spinnaker, sometimes we are able to make our own wind out of the slightest puff. By never giving up, we position ourselves for when the wind does return.

Leading a growing business, or a winning crew, requires a creative plan, a dedicated and collaborative team, the right use of technology, and the resilience and courage to take advantage of whatever the market, or nature throws at you.

Leading a winning team is exhilarating, and it's why I race every year, and jump out of bed to go to work every morning.

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David Ormesher, CEO

Founder and CEO of closerlook, a recognized leader in creating innovative relationship marketing solutions that help pharmaceutical companies get closer to their most important customers. Learn more about closerlook here.

 

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