Few NFL team owners are the face of their teams the way Jerry Jones is with the Dallas Cowboys. As the owner, president, and general manager, he is a man of many roles, and, unfortunately, perhaps too much ego.

Jones, for all his extreme personality and undeniable success, has failed to understand that he is not a good NFL general manager and should have launched a talent search to find someone who is. But that was ego getting in the way of wise business decisions.

In that sense, he is much like many visionary entrepreneurs who launch companies successfully, but fail to recognize that, once the business is thriving, they may no longer be the best person to handle operational responsibilities and take the enterprise to the next level.

Passion and Perseverance

Jones was not the Cowboys’ founder. They were established in 1960, about three decades before he acquired the team. When he bought the team in 1989, it was losing $1M per month. Over the next few years, they won three Super Bowls, and under his leadership, the Dallas Cowboys became the most valuable sports franchise in the world—now worth an estimated $10B–15B. He built a brand that transcends football.

That last Super Bowl victory came three decades ago, though. Since then, the Cowboys have become an NFL afterthought, a team that on occasion flirted with success, but struggled to return to their football throne and one-time lofty position as “America’s team.”

Certainly, Jones is a successful businessman. There is no denying that. Despite the years of Super Bowl frustration, the Cowboys are the NFL’s most valuable team. So kudos to Jones and the franchise for that.

In that sense, he has demonstrated grit in action, what author, academic, and psychologist Angela Duckworth calls “passion and perseverance for long-term goals.”

Jones had that. He still does.

But grit, Duckworth warns, isn’t always enough. Especially when it’s not paired with humility and the ability to learn from peers.

Imagine if Jones had checked his ego long ago, confronted his limitations, and hired a talented general manager to guide the Cowboys back to the heights they once knew. As successful as Jones has been, he and the Cowboys have missed out on immense value that would have been even greater if the team had won two or three more Super Bowls in the last 30 years instead of watching from home as teams like the Patriots and the Chiefs dominated. In such a scenario, the Cowboys might have roughly 25% more value, translating into $2B or more.

A Different Skill Set

Founders of businesses often struggle with the same thing Jones does: an unwillingness to let go of some of their responsibilities and empower others with special talents to handle key operational aspects of the business.

Many such entrepreneurs are visionaries who excel at seeing the big picture, but don’t always shine when it comes to handling operational responsibilities of the business as it matures.

The skill set required to envision, found, and create a viable business is not necessarily the same as the skill set required to truly scale the business. Many founders eventually reach a fork in the road where they recognize that the next phase of growth demands something or someone different.

That’s not a failing. It’s just evolution.

This person had to have an immense amount of passion and fortitude to get to that point, and that passion doesn’t typically disappear. However, Duckworth’s research does show that grit must be cultivated, not just possessed. And that means associating with peers, seeking feedback, and embracing discomfort. She even says, “Join flotillas, don’t sail solo.”

There are common inflection points that push founders to rethink their roles:

• • They don’t want to take on the next big financial risk.
  • There are differences in vision among other key stakeholders.
  • A lack of succession options or challenges with family involvement dynamics.
  • An unwillingness to bring in and empower new leaders with specialized skills.
  • A realization that their leadership team lacks expertise in certain areas to truly scale.
  • Sometimes, there are emerging health issues or simply the toll of the work over time.

These aren’t easy truths to face. But the toughest decision the founder sometimes makes is acknowledging, “I’m not the right leader for what I’ve done in the past.”

Letting go doesn’t necessarily mean stepping away. It means stepping up and trusting and empowering others with roles that enable them to lead, build, and create new success with their own special talents.

And maybe that’s the cold, hard truth that Jerry Jones has struggled with and been unsuccessful in overcoming himself and for his organization.

The Cowboys are still a juggernaut. But they could have been a multi-decade dynasty.