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Volume 20 No. 45
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Tom Ricketts, Chairman, Chicago Cubs

The Cubs come with their challenges, but Ricketts enjoys being out with the fans and has a work-life balance that he couldn’t find in investment banking.

Leadership in a sports organization is about three things. No. 1 is, the way you act and the way you behave sets the tone for the entire organization. I want everyone in our organization to see the way I treat customers, treat fans, treat sponsors, and we need to have a whole culture built around that first-class service.

Second thing you have to do is set the goals. We have a lot of things to accomplish. We have incredible opportunities, we have to basically communicate where we are going to go with these things, what our goals are and how we’re going to get there.

No. 3, and maybe the most important thing, is finding the right people to be on the team.

One thing I know for sure is my tenure as chairman and the Ricketts family ownership will be defined by one thing, and it’ll be, Did we win or not?

A leader needs to be visible. I don’t know how you can be a leader and do it in abstention. You have to be out there. You have to know your people and know what they’re trying to accomplish and support them and be seen as part of a team or someone who is leading a team.

I’m in the office most days. I’m at every home game, and so myself and the family itself are very visible.

I walk around every home game for five to six innings and I talk to everybody. It’s important to me. It’s the favorite part of my day. I really do enjoy talking to people and seeing how their day is going and cheering with them and being a part of the scene at Wrigley.

Cub fans have such a deep passion for the team and the park, and I want them all to know that we share that passion and we feel the pain in the losses and the joy in victories just like they do.

There are days where it’s cold and it’s wet and [I’m] sitting up in my nice dry room having my lunch, and [I’m] like, ‘Jeez I have to go out and talk to people,’ and there are days where it’s not what I really want to do today, but the minute you meet that first person, that all changes and it becomes the best part of every game.

There’s this misperception that everyone at Wrigley is there just to drink beer and meet somebody. The fact is most of our fans are very knowledgeable.

The other thing that’s been very impressive is, everyone understands what we’re doing. We’ve been very clear that this is an organization that’s going to do things the right way. We’re going to build a baseball culture that is smart, consistent and on a path to be a contender every year, and people get it.

This work-life balance is a big improvement over my previous job, which was running an investment bank with an international office. When I’m not home at night, I’m just 10 minutes down the road. And we live right on the L line in Chicago, so my kids can come to any game they want — just pay $1.85 and they are there.

When we were kids, we had a family business. My father was starting a brokerage firm. By the time that we were in our 20s, it got too big to be a family business. Part of the reason why we wanted to buy the team was it’s a real family business and it brings everyone together. It gives me a lot of time with my siblings.

One of the hardest things about recruiting people is you’ve got to find complementary skill sets. Your nature tells you to hire someone just like you, but you have to be careful to overrule that to make sure you have the strongest team in place.

Beyond just complementary skill sets, you need people that want to work hard, that are optimistic, that can get along with other people, because just like there is a team on the field, there is a team off the field and they have to work together.

In hiring, it’s important to talk to people who they’ve worked with in the past. You can get a lot out of that. People are very circumspect about what they’ll say if they had a bad experience with that individual. But if they had a good experience with that individual, you’ll know.

Ultimately the best way to do any homework on a potential person to bring on a team is to talk to people they’ve worked with, and hopefully those are people you trust.

One of the things we instituted this year is a sponsorship program with Northwestern’s business school to create a certificate program for our great young people so that not only will they get the on-the-job experience of just their daily job, but get broader perspective. It really adds to their résumé, and it’s had a tremendous response.

Sports are obviously very fortunate in the fact that you have the ability to pick and choose who you want to bring in because there are so few opportunities and so many people that want them. Once they’re in and you have the right people, you’ve got to do the right thing for them and focus to make sure [you] retain them.

In a typical business, you have a great young person, you go let them run the London office. The Chicago Cubs don’t get a London office. So you have to focus on internal opportunities and then supplement them with some type of education outside that will help round them out.

I have five kids. The oldest is 17, and the youngest is 7. When my wife and I are away on vacation I disconnect a little bit. I really disconnect best in the mountains, particularly when I’m fishing.

There are mornings where you wake up at 3:30 a.m. feeling that 20 million Cubs fans are standing on your chest because you just have such a huge obligation to make sure that everything we do builds toward that championship.

We have a great management team, so I don’t sweat the details. I just sweat are we doing the right big-picture things to get that championship to our fans.

I do love reading baseball history. At night, before I go to bed, I try to not read baseball because I’d end up dreaming about it all night.

My favorite books are the Patrick O’Brian books [author of “Master and Commander”]. I read them like 20 years ago and now I’m re-reading all of them because it just takes you away. Ten minutes before you go to bed and you’re reading about a far-away place with far different issues, and it’s a great way to unwind.