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The Myth of the "Winning Culture": Why Chasing Wins is Holding Your Organization Back


June 14, 2025 | Read online

The Myth of the "Winning Culture": Why Chasing Wins is Holding Your Organization Back

by Kevin 'KD' Dorsey

Picture this: you’ve got a sales team that’s absolutely crushing it. They’re hitting every target, closing every deal, and it seems like they’ve got that “winning culture” nailed. But then, the moment they miss a quarterly goal, everything falls apart. What happened to that winning culture they had going on?

Here’s the hard truth: winning isn’t a culture; it’s a result. And if your culture relies on winning, you don’t really have a strong culture at all. I’ve been there—I’ve seen teams that look like they’re on top of the world when things are going well, but the second they hit a bump in the road, they crumble. That’s because a real culture isn’t about the results you get; it’s about the behaviors and values you live out every single day. Let’s get into why obsessing over a “winning culture” could be the exact thing that’s keeping your organization from long-term success.

I’ve been in the trenches, building and motivating high-performing sales teams. I’ve done my homework on organizational culture, and I’ve been with teams through the good times and the bad, when we’re hitting our numbers and when we’re missing the mark. What I’ve learned is that the popular idea of a “winning culture” isn’t just wrong—it’s actually holding you back.

Winning is an Outcome, Not a Culture

Let’s get this straight: winning isn’t a culture. Winning is just a result. And if your culture depends on winning, you don’t really have a strong culture at all, do you? I mean, what even is a “winning culture”? What does that actually mean? To win, you’ve got to act a certain way.

Let’s break this down. When people talk about a “winning culture,” they usually mean a culture where everyone’s motivated, on the same page, and performing at their best. But those are behaviors and processes, not the result itself. Winning is what happens because of those behaviors, not the culture.

Take the New England Patriots, for example. People always say they have a “winning culture,” but what’s really driving their success? It’s their dedication to being prepared, holding each other accountable, and always getting better. Those are the behaviors that lead to winning, not some vague idea of a “winning culture.”

On the other hand, think about organizations that have won without a “winning culture” mindset. Companies like Enron and Lehman Brothers were all about winning no matter what, and we all know how that turned out. They cared more about results than behaviors, which led to shady practices and, eventually, their collapse.

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The Real Culture Drivers of Success

So, what actually drives a successful culture? Organizations that are killing it have well-defined things like credible leadership, a clear vision, core values, and specific practices that shape their culture. Culture is what drives performance, not the other way around.

Organizational virtuousness promotes well-being, optimal performance, positive organizational image, and competitiveness by encouraging virtues like appreciation, gratitude, and encouragement. According to a study by the National Center for Biotechnology Information (NCBI), these virtues are critical for long-term success.

I’ve experienced this firsthand. I thought we had an awesome culture. Everything was going smoothly. Everyone was getting along and working hard, you know? When we were winning, everyone was supportive. But as soon as we started losing and missing our targets, that culture disappeared in an instant. Missing your numbers quickly exposes a bad culture.

Now, compare that to organizations that prioritize accountability, continuous improvement, and putting people first. Companies like Google and Zappos have built cultures around these virtues, and they’ve seen long-term success because of it. They don’t just talk about winning; they live out the behaviors that lead to winning.

How to Build a Truly Winning Culture

So, how do you actually build a culture that leads to winning? Culture is all about behaviors. What are you known for? What do you want to be known for? If your culture depends on winning, you don’t really have a strong culture at all. It’s just a facade that falls apart as soon as the results start slipping.

First, define your core values and make sure they’re lived out every day. That means hiring, firing, and promoting based on those values. It’s not enough to just talk about them; you’ve got to walk the walk.

Second, focus on continuous improvement. Encourage your team to always be learning and growing. This creates a culture of resilience that can handle the ups and downs of hitting and missing targets.

Third, put people first. Show appreciation, gratitude, and encouragement. This builds a positive organizational image and promotes well-being, which are critical for long-term success.

Finally, avoid the trap of mixing up outcomes with culture. Winning is an outcome, not a culture. Focus on the behaviors and values that lead to winning, and the results will come.

Conclusion

Winning is a result of culture, not the other way around. As leaders, we need to focus on shaping the right cultural drivers instead of chasing some mythical “winning culture.” By prioritizing behaviors, values, and continuous improvement, you can build a culture of excellence that leads to long-term success.

So, let’s stop chasing wins and start building cultures that lead to winning. What are you known for? What do you want to be known for? The answer to those questions will determine your long-term success. Let’s build cultures of excellence, one behavior at a time.


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Sales Leadership Accelerator

Learn how to boost your sales team, drawing from KD's vast experience as a team member and a sales leader. This newsletter outlines the exact methodology KD used to build multiple sales teams and unicorn companies.

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