Leadership Lessons from Wrigley Field

We’ve all been thinking about leadership a lot lately.

Living in the northern Chicago suburbs, I’m a fan of the World Champion Chicago Cubs. (Finally hearing that never gets old.) What’s been most fascinating for me has been watching this young team influenced by the leadership work of their manager, Joe Maddon, who will likely have Michigan Avenue renamed in his honor.

Because of my background, I tend to see leadership styles through the lens of music education. A comparison thought finally struck me the other day that made complete sense. Joe Maddon is like that music teacher who comes along, takes over a small music program that’s never amounted to much, and makes it soar to dizzying heights of success.

We’ve all seen it happen. A music program with a revolving door of leadership that constantly struggles. All of a sudden–presumably out of nowhere–a new director has kids coming out of the woodwork to participate. Then they’re starting to sound good at state festival. The parent booster organization becomes this well-oiled machine of fundraising, uniform-organizing, equipment-moving experts. The students carry themselves a little taller. Then they’re the “have you heard this group?” buzz at the state music conference. It doesn’t happen overnight–and certainly neither did the Cubs– but it happens.

So what’s the trick? If we can draw parallels to what we just saw leading up to the World Series, it might be this.

Believe. Sometimes when a music program has been down long enough, they never expect to achieve anything. That had certainly been the case with the Chicago Cubs. But Maddon has said that he doesn’t believe in the infamous Cubs’ curse. His philosophy was to acknowledge the past, but expect something good to happen and not wait for the worst. And he summed it up best in the press conference after the big win: “If you just want to carry the burden with you all the time, tonight would never happen.”

The process is baby steps. Neither Maddon nor team president Theo Epstein set out to win the World Series their first year. But that was very clearly the eventual goal. They knew where they wanted to go and that it would take time and victories large and small on the way. Step-by-step methodical approaches and planning…along with some good fortune…all led to that final win in Cleveland. And that is how any good music program will grow.

They do what works for them. One of the things that usually made the news here in Chicago were their “themed” road trips. Traveling in pajamas. Wacky suits. Football jerseys. While this probably wasn’t something that most professional ball clubs would do because of the silliness factor…this was something that Maddon believed would catch on with this team of very young players. What it did was allow these ballplayers to relax, let their guard down a bit, trust each other, and enjoy the experience more. Which leads to the next point.

If it’s not about winning, you’ve won. One of Maddon’s philosophies has been “Never let the pressure exceed the pleasure.” The day they needed to leave Chicago for Game 6 in Cleveland was October 31. Rather than get to Cleveland early for more practice, he had the players take time to take their kids Halloween trick-or-treating. In a situation where every game was a “do or die” circumstance, they instead took time to remember to have fun.

They arrived rested and relaxed, and the rest is history. They take ownership. In that final game of the Series, when what looked like another Chicago Cubs death spiral was beginning to form and the rain delay hit, it was outfielder Jason Heyward who is credited with rallying the team in the locker room during the delay break. Maddon, who famously hates meetings, was in the dugout checking the weather report. It was the ownership that the individual players had taken in achieving the overall goal that motivated them to regroup, refocus, and move forward.

There was a magical quality watching this season unfold, just like there is when you watch an underdog music program finally succeed. You know that great things are happening, and you look forward to what might be coming next.

This issue of SBO Magazine celebrates 50 outstanding educational leaders who continue to be a “Joe Maddon” in their field. As you read through the profiles you will see common themes that reflect the servant leadership by which these individuals live day to day. Moments of student accomplishment, seeing them overcoming adversity in various shapes and forms. Creating the inner spark that leads to their students’ ownership of life goals. Pursuing excellence together with the life skills and work ethic that subsequently develop. Focusing on the process, knowing the product will follow. Finding joy in the journey and “the love of the game”.

To these Most Valuable Performers, to the many mentors that shaped them (and us), and for the countless lives that will be better because of their efforts—we say a heartfelt “thank you.”

Tom Merrill is the Executive Director of Festivals of Music, with over 25 years of experience as a band director, travel planner and festival organizer.