The first in our series of leadership lessons, culled from coaching greats.

We’ll scour the best leadership books, blogs, and theory for ideas that can make you be a better leader.

Photo by Miguel Bruna

America is addicted to winning. We start our kids as early as four years old in PeeWee soccer and by the time they reach Little League, we are practically coming to blows with other parents and coaches about our ten-year-old’s teams.

When those kids get to school, they study about wars, and how history is written by the winners. Then they enter a mad race to beat everyone else by winning a coveted acceptance to the best college.  Their social media feeds are littered with people boasting about how they won the genetic lottery of looks, the inherited lottery of rich parents, or some other sporting or academic feat.

So it is little wonder that we take this compulsion to win with us into adulthood. Charlie Sheen even gave it a hashtag:  #winning.

This isn’t bad.  So we’re all high achievers, big deal.  But does the reflex to “always win” also creep into your conversations?  Maybe even at work?

According to legendary coach Marshall Goldsmith, many successful leaders get themselves into trouble by bringing their addiction to winning to everything:

Winning too much is the #1 challenge for most people, because it underlies nearly every other behavioral problem. If we argue too much, it’s because we want our view to prevail (in other words we want to win). If we put other people down, it’s our way to position them beneath us (again, winning). If we withhold information, it’s to gain an edge over others. If we play favorites, it’s to gain allies so “our side” has an advantage.”

Marshall explains that our obsession with winning can be even more toxic at home. We come home from an exhausting workday, take off our coats, and get greeted by our loved one, anxious to regale us with stories about her bad day. What do we do? Comfort her?  Listen? No. We one-up her by comparing days, as though we need to “win” at having had a worse day.

Or, we argue about where to eat, and if we lose, and then the dinner sucks, we complain the entire time so we can “win” in retrospect about where we should have gone.

Any of this sound familiar? We’re pointing this out because many high achievers (i.e., leaders) fall victim to this tendency, and it’s pretty simple to stop once you become aware you’re doing it. If you find you’re guilty of it at home, you’re probably also doing it at work. And from a leadership and teambuilding perspective, it doesn’t make for a happy and productive workplace.

In Ryan Holiday’s new book Stillness is the Key, he points out that all great leaders and thinkers slow down, pause, and give themselves a chance to think before they move forward.

During that momentary gap between reaction and response, we have a chance to consider whether this one-upsmanship we are about to engage in, this “I was right” battle we are about to undertake, or this employee we are going to correct/edit/override is truly going to get us the best long-term performance from that person.

Photo by Kalen Emsley

Whether you call this pause Stoicism, mindfulness, or just walking in the other guy’s shoes, we could all use some self awareness on whether we are perceived the way we wish to be, or whether we need to examine our own behavior and overcome some of our natural human flaws.


Cultivate is a digital leadership platform that leverages artificial intelligence (AI) to provide in-the-moment feedback and tools to enterprise employees. Our mission is to help build stronger workplace relationships, and empower people leaders and employees to be more effective, engaged, and balanced.

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