Lead to Win: Lessons from a Chicago Cubs’ World Series Champ


I’m a die hard Chicago Cubs fan. As much as I love all Chicago sports, baseball is what I grew up watching. I am by no means the longest living Cubs fan, not even close! However, I, like many others, grew up watching them lose a lot, hanging onto every inch of hope that they might just win it all one day. So, when they finally did it this year, I was literally ecstatic. I cried; I admit it; I have no shame about it.

The thing about this current Cubs team though that makes me such a proud fan is its leadership. Being a leadership and HR fanatic myself, its one of the first things I notice in teams. The Chicago Cubs has a lot of great leaders from Theo Epstein to Jed Hoyer to the Ricketts family. However, I am consistently impressed by the great Joe Maddon.

So, here’s what I’ve learned about how to “lead to win” from Joe, manager of the World Series’ Champs, the Chicago Cubs. I’ve titled each lesson after my favorites of Joe’s “Maddonisms.”

“That’s outcome bias.”

Joe often responds with this statement when the media questions a decision he made, claiming that the opposite decision or a different decision could have had a better outcome. In leadership, we often play it safe and if something goes wrong, we constantly waste time questioning “what if” scenarios, attempting to breakdown what went wrong. There is a false assumption that another decision or action would have resulted in a different outcome, when in reality, no one really knows. It could have been the same outcome either way.

The lesson is that just because one decision or risk does not work out, it doesn’t mean that we need to play it safe the next time. We must keep taking chances and pushing boundaries.

“Do simple better.”

Joe is questioned a lot for his way of leading and managing the Cubs. He cancels batting practices and doesn’t hold team meetings. Instead, he believes that he has adults and professionals on his team and thus, he should treat them as such. Therefore, he puts his trust in his team and doesn’t micromanage them. Guess what? They chose to practice anyway and took the World Series in style, coming back from 3-1 games down to win it all. He also prides himself in having one-on-one conversations rather than team meetings.

The lesson for leaders is to stop overcomplicating our roles. If we do the simple things better, we will already have better results. One piece of advice from Joe is to not micromanage every detail of how employees should do their jobs. Be clear with expectations and let them achieve the results on their own. The other relevant lesson is that when someone isn’t performing, have a real, honest conversation with that person rather than holding a team meeting every time to reset expectations in a passive-aggressive manner where everyone feels like they did something wrong but aren’t really sure.

“You have to have a little bit of crazy to be successful.”

Crazy doesn’t always mean that someone requires medical attention. It means doing things out of the ordinary. It means taking some chances, some risks. It means pushing ourselves out of our comfort zones. It means thinking differently. It means going against the tide sometimes. It might even mean standing alone. But, that’s what real leaders do.

The lesson for leaders is to stop worrying about what everyone will think or making everyone happy and simply, start doing the right thing even if it means making some bold decisions or taking some unpopular actions. We need to be a little crazy to do things despite our fear of failure. So be it. Great leaders are a little crazy!

“Don’t ever permit the pressure to exceed the pleasure.”

This is my favorite maddonism! Every Cubs fan knows about the team’s themed road trips. This year, they did eccentric suits day and a pajama party day. Joe also throws little parties in the clubhouse like when he brought zoo animals in for spring training or brought in a mariachi band to serenade his team before a game. The lesson here is to have fun with our teams and let them have fun with each other. Fun brings people together and takes the pressure off.

This maddonism also gets to the heart of success which is that people who love what they do will achieve the best results. Why? It’s not likely that people love doing something they are not good at. People with real passions live and breathe whatever it is that they are passionate about. Leaders hire A players and let those A players enjoy what they do because the pleasure of we do everyday should exceed the pressure we are under.

What stands out for you and what might you try doing with your teams? I’ve been pondering the “no team meetings” idea. Here’s to the Chicago Cubs, to Joe Maddon, to leadership and to all of you winning with your teams!

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