What does it really take to win? I asked baseball’s best leaders.

Five insights that will change the way you approach success, on or off the field

We’re days away from what’s going to be an epic World Series featuring the Brewers and the Rays.

And as the two best teams in baseball get ready to compete on the biggest stage, I keep thinking about the leaders I’ve spoken with over the years who have built winning organizations in and around America’s favorite pastime.

I’ve pulled together 5 lessons from some of baseball’s best leaders that you can apply in your own world to build a winning team.

1. Winning starts with preparation long before the big moments

Ben Zobrist, 2x World Series Champion

Ben Zobrist won two World Series rings – first in 2015 with Kansas City, and the very next year with the Cubs, where his double to left field in Game 7 brought in the series-winning run.

But when he stepped up to the plate, he had to be feeling the pressure. How was he able to perform in a moment like that? When I asked him, his answer was simple: it wasn’t about the moment at all.

Ben says a lot of people make the mistake of only paying close attention to the work when the moment starts to feel big. But the best players prepare themselves in the shadows, when nobody’s watching and nobody cares. That way, when the lights are bright and the pressure’s on, nothing has to change.

Don’t wait to prepare for the big moments in your future. If you want to succeed when it counts, you’ve got to put in the work when it doesn’t seem to matter.

Reflect: How are you developing yourself and building your readiness right now for the big moments in your future?

2. Winning means making the vision personal

Rob Manfred, MLB Commissioner

Rob Manfred leads a league of 30 independently owned franchises, and they each have their own interests and agenda. But for Rob to be successful as commissioner – and for the league to grow – he’s got to get alignment across that whole group.

So yes, he’s got to have a compelling vision for the league. But he can’t stop there. To succeed, he’s got to make that vision feel personally relevant to everyone in the room.

As a leader, having a vision is only part of your job. You also need the ability to show people how executing against that vision helps them individually. When you can make that connection, it’s so much easier to make your vision a reality and achieve those big goals.

Reflect: Have you taken the time to show each person on your team not just where you’re going, but also why it’s good for them personally?

3. Winning cultures are learning cultures

Greg Johnson, Owner, San Francisco Giants

For Greg Johnson, a winning culture is a learning culture. And it starts before someone even joins the team.

When he hires, he looks for curious people – the ones who ask questions, bring energy, and are willing to get uncomfortable. Once they’re in, he encourages them to reach across the organization and connect with people outside their function.

When your whole culture is wired to learn, it shows in the results. Curious teams ask smarter questions, embrace new ideas more readily, and recover from mistakes faster.

Reflect: Are the people you’re hiring curious and eager to learn? And how does your environment nurture and reward that curiosity?

4. Winning takes a clear process

Terry McGuirk, Chairman, Atlanta Braves

Of course, anyone who works in the sports world wants to win.

But as a goal, “winning” can feel a little one-dimensional.

That’s why Terry McGuirk wants his team to focus more on how they execute their process – what they call the “Braves Way.”

He points out that over a 162-game season, if one team is just 3% better than another in how they execute their process, the difference in the win column is dramatic. So instead of chasing wins directly, they pursue what he calls “endless perfection” in how the organization develops players, makes personnel decisions, and runs the business side.

As leaders, we can get so narrowly focused on goals that we forget to zoom out and deeply consider what habits, behaviors, and strategies will actually make those goals a reality.

Reflect: What’s your version of the “Braves Way?” Do you have a clear process your team believes in, or are you just chasing results?

5. Winning requires betting big on what makes you unique

Jesse Cole, Owner & Founder, Savannah Bananas

If you’ve seen dancing baseball players in your social media feed lately, that’s because of Jesse Cole.

He’s the owner and founder of the Savannah Bananas, one of the most talked-about teams in sports. And they’ve done it not by trying to be the best team in baseball but by being unlike any other team, period – with a “fans first” philosophy that has them selling out stadiums.

The question Jesse asks to be successful isn’t “how do we beat the competition?” It’s “what can we do that no one else is doing?”

That mindset shapes everything they do. Jesse challenges his team to take risks. He doesn’t want to do the same things a little better or cheaper or faster. He wants to find things nobody else is doing and make their mark that way.

Great companies embrace that risk-taking creativity and find ways to uniquely excel and stand out, not just imitate everybody else.

Reflect: What can you do that your closest competitor can’t replicate? Lean into it – and if nothing comes to mind, take some time to consider what that stand-out quality could be.

I’ve always believed that sports offer some of the best leadership lessons around – and baseball is no exception. (You probably know this if you’ve seen my past articles with wisdom from leaders in golf, football, and basketball!)

Whether you’re following the MLB postseason or not, I hope these five lessons give you something to think about as you build your own winning team.

Which of these resonates most with you? Drop a comment with your thoughts, and let me know who you’re picking to win the Series!