Success in Business through Sailing

Published on August 17th, 2017

Scott Windsor, vice-president of Meridian Credit Union, shares in The Globe and Mail how he learned workplace lessons from a sailing course.


Scott Windsor

There’s nothing like falling into Lake Ontario, your 16-foot Albacore sailboat capsized, to focus your attention on the task at hand.

Executives and senior managers are supposed to steer the organizational ship in the right direction. It’s quite a splash in the face to try to master that using an actual boat.

I’ve enjoyed many leadership development opportunities. This summer, I had one of the best. It didn’t come in a corporate setting, but when I learned to sail over five weekends.

Here are some lessons I’m taking back to work.

Get comfortable with failing
After we learned to rig the boat, the first thing our instructors J.P and Hugo made us do was tip it. They knew we would anyway at some point, so they wanted us to get it over with. When you know what failure feels like, you lose your fear of it.

Failing is part of life and business, but the thought of it can paralyze you. It shouldn’t. Give your people room to fail. When they see that they can right the ship and learn from the experience, that’s real growth.

Learn from everyone

I’m programmed to think that the more senior members of the organization are the ones with the most knowledge to share. In your company, would you take direction from a teenager? J.P. and Hugo were just 19, but they started sailing at age 9 and are experts at their craft.

Don’t assume what members of the team bring to the table. No matter someone’s age or experience, they have unique talents and perspectives. At work, I’m responsible for directing my team’s development. Often, I forget that I have lots to learn from them too.

Rotate the team
We used two-person sailboats, each week with a different partner. In part, we became better sailors by continually adapting to and learning with new people next to us.

In the corporate world, we can get stronger when we mix up teams. Changing the dynamic forces you to adjust. You become more flexible and open to new ideas and ways of doing things.

Learn to be both captain and crew
The skipper is perceived as the more valuable position, but all roles are important on the water. Your job as a leader is to identify, communicate and rally people around a shared goal. Each team member contributes. You wouldn’t want to take your boat out alone.

Move quickly from strategy to execution
In corporate life, I’ve spent countless hours developing, debating and reporting on strategic recommendations. You go through all the scenarios and what-ifs. Yet on the water, J.P. and Hugo had me sailing the boat on just my second lesson. This was learning-by-doing.

It reminded me to tell my team that sometimes the best strategy is to just go for it. With any endeavor, you can review the pros and cons endlessly, or you can take the plunge. You’ll either be on the road to success or learn what doesn’t work. Either way, you’re ahead that much sooner.

Remove your distractions

When taking the boat out, we couldn’t bring our phones for fear of them getting wet. So there were no calls, e-mails, texts, checking Twitter, etc. We were able to concentrate fully on one thing only – learning to sail.

In the workplace, there are many demands for our attention, and they might all seem important at the time. It’s easy to lose focus on Job No. 1. Don’t get pulled off course.

Don’t wait for the winds to die down
We weren’t supposed to sail in winds over 15 knots. On the day of my second lesson, the wind measured 20 knots, yet we went out anyway. J.P. and Hugo told us that we’d learn more in those conditions.

It was a great reminder that your toughest assignments also teach you the most. Keeping the boat up was challenging that day but incredibly instructive. If you only venture out when the winds are still, you’ll never really improve or know how to handle adversity.

On the water or at work, sometimes staying in your safe zone is the biggest risk of all.

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