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By Darryl Stewart
How to avoid winning at all costs

How to avoid winning at all costs

A few weeks ago I attended an immersive three-day leadership course. I was excited and afraid at the same time. I was excited because I had applied in the past and had been denied; I was afraid because the course was going to be held in the U.S. and the students were 90% American. You see, I have a bit of an anti-American bias when it comes to leadership. Being in high technology businesses for over 20 years, I have met many American leaders and, as all Canadians are, I am perpetually exposed to American culture. My pet peeve? The drive of many Americans to win at all costs. I have seen several business dealings go bad when the American side of the deal gets obscenely greedy going for short-term financial wins. I have had to sit through discussions with U.S. entrepreneurs who are living beyond their means, trying to live the dream and putting themselves in situations where they constantly need big wins to keep their heads above water. I have experienced the bragging and bravado, and I have had my fill of the U.S. sports culture where anything goes if you can get the win. This is balanced, though, by the fact that your typical American is friendly, likeable, open – basically Canadian (well, almost).

As expected, I liked everyone at the course as individuals. Then came the sports analogies, the come-from-behind stories, and the try-hard-enough-and-you-will-win stuff. My fears were being realized. I was starting to wonder why this course was loved by leaders from all over the world and from every background. Then the answer came. The person spouting these winning stories – our guru and leader, an advisor to five U.S. presidents, and a world-famous entrepreneur – turned the table on us and said the words that brought it home for me:

“Winning does not matter if you compromise your values in the process!”

In that moment I saw the problem with so many people I have dealt with. I also saw the reason for the overwhelming success of so many powerful leaders I admire – people who have built things with lasting value. They have the “American” drive to win, but they combine it with positive personal values by which they lead and live. They have ethical lines they will not cross and they have positive things they are trying to accomplish in life while they do all they can to win.

If you have done your absolute best to win at whatever your game is, while still sticking to your values, then you have not won “at any cost”. You have won no matter what the actual outcome is. This sounds typically Canadian doesn’t it? Too bad, eh? 🍁

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  1. You’re absolutely correct. Our values are priceless and shouldn’t be squandered.

IBEX Payroll extends our profound respect and immeasurable gratitude to all the ancestors and keepers of the land on whose traditional territories our work takes place. We acknowledge that we are on Treaty 1 territory, the traditional gathering place of the Anishinaabe, Cree, Oji-Cree, Dakota and Dene people and the traditional homeland of the Métis people. This land is sacred, historical, and significant. 

Every time we acknowledge this truth, we have an invitation and an opportunity to reflect on the wrongs of the past, what we do in the present, and what we can do to continually honour the people whose lands and water we benefit from today. 

This statement only acts as a first step in honouring the land we reside on and its peoples, and must be paired with education, understanding and informed action.