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How to Create a Winning Team: The Chicago Cubs’ Secret You May Have Missed

At the time of this writing, the Chicago Cubs are headed to the National League Playoffs. (Sorry Cards fans, but this former Chicagoan sings “Go Cubs, Go.”)

Fascinated as we are with underdogs and lovable losers, there’s been endless analysis of why the Cubs are now post-season players.

Young sluggers Jorge Soler, Kris Bryant, and Kyle Schwarber.

Consistent, fuzzy-faced pitcher Jake Arrieta.

Or the modest but talented horn-rimmed Joe Madden managing from the dugout.

But they’re missing the point. The Cubs employed one major strategy to create a winning team. And it’s a strategy you can use to create a winning team in your organization, too.

The Back Story

I’m not a sports historian. And I’m no baseball expert. And I haven’t been to Wrigley Field in person for 15 years.

But there are enough of you, including reporters and fans, who’ve been telling the story of the Cubs’ progress ever since the team was sold by the Tribune to the Ricketts family (the founders of TD Ameritrade) in 2009.

And recently, Talent Management magazine (a human resources trade publication) ran a behind-the-scenes interview with Bryan Robinson, a former GE exec who joined the Cubs to lead HR.

This article shared that on Robinson’s first day in 2012, the Chicago Cub’s HR department—the department responsible for any organization’s most important asset, its people—was based in a trailer. Computer servers were covered in tinfoil to keep out the rain.

But HR wasn’t the only one struggling. Group ticket sales—the lifeblood of a professional team—were handled on carbon paper.

So there’s nothing inherently wrong with tinfoil and carbon paper. ButIs your organization propped up? sticking to what’s worked in the past is fine—if you want to stay exactly as you are.

The Ricketts did not. So, as they put Robinson and other new leaders in place, they got moving on one big thing:

Investing in the Infrastructure

And that’s the secret to how to create a winning team.

Really? Infrastructure?


Sorry. That’s the secret.

Sure, it’s not as sexy as a new training technique that you can brag about at the Chamber event (“Oh, our entire company is taking the new Bubba Gump Service Training. . . “)

It’s not as fun as just winging it (“oh, we don’t want to overprocess things. We’ll just let our team figure it out . . “ )

Naw. That doesn’t work if you want to create consistent, winning ways and build consistent, engaged and successful teams.

What Do We Mean By Infrastructure?infrastructure is how to create a winning team

Let’s take a step back. When we’re talking about a building, infrastructure is how we refer to all the elements that are needed to make that building work. Plumbing. Electrical. Roads to get in and out of the location.

So for your company, department or team, infrastructure is all the foundational stuff that makes our work work.

Our sets of values, rules, tools, and standards.

Our chosen programs, processes, and ways to get work done.

It sounds easy and basic. But it’s not.

What Gets in the Way of Creating Infrastructure

Creating and maintaining infrastructure is time-consuming, discipline-requiring, and sometimes just plain boring.

No wonder we procrastinate it or avoid it altogether, patching together workarounds when we know the job just needs to be done right from the ground up.

But infrastructure is the essential (and literal) foundation to your business and your team.

How do you know if you need infrastructure? Start by asking yourself these two questions:

How do we do things here?

What are the tools and rules we use here?

If there are multiple answers for those questions, or if no two people answer the same question the same way, you’ve got an infrastructure problem.

How I Learned the Importance of Infrastructure

When I was the volunteer president of a large, local trade association, I had all kinds of dreams and plans for what we’d do during my term.

As a creative person, I had a million “good ideas” we could implement to better our goals. I imagined winning awards and kudos at the end of my term, and people would glowingly talk about me when I was gone . . .

(Screeching halt sound.) Yeah. Right.

do you need infrastructure to create a winning team?

Yes, I’m creative, but I’m a business person first. And when as a board we looked hard at what the organization really needed most, It was infrastructure.

Agreements. Common tools and rules.

Not sexy by far. Not anything most people would even notice . . . until they noticed that the organization was dead.

Because we’d grown big enough that the “just get it done” mentality that works when you’re smaller was wasting time, money, and energy.

We needed to get an updated contract in place with the company that provided administrative services. We needed to clarify and recommunicate the goals and expectations of board and committee members—and then hold people accountable to those expectations. We needed to make tough decisions to get on a better financial footing, including eliminating a popular, ego-boosting but but money-losing event.

At the end of the year, we got it done. I’m grateful for the mentors and coaches who helped me get over myself, disappointed not to be the superstar leader who launched a new, glamorous program or who pulled in hundreds of new members.

I settled with knowing I was a leader who did the right things. And sometimes, that just has to be enough.

How You Can Create Infrastructure for Your Team (Even If You’re Not HR)

You don’t need to wait for someone else’s approval to start creating infrastructure.

Ask your team the two key questions. . .

How do we do things here?

What are the tools and rules we use here?

If you get similar answers, congrats! You have structure and agreement, and you’re on your way to creating a winning team.

If you get different answers from everyone, then start with building one regular, predictable thing. I’ve worked with my leadership coaching clients to create elements of structure such as:

  • The one-on-one monthly check-in meetings, with a short, standing agenda that people can plan for, and with your commitment not to cancel it if “something more important” comes up last minute. (‘Cause if your people are not the most important use of your time, then why do you care about building a winning team at all?)
  • The way you incorporate acknowledgement and celebration of the small, positive elements into your everyday work (such as starting a group meeting with “Before we begin, let’s take 30 seconds each and tell each other what we’re proud of this week.”)

How Humans are Like Tomatoes

Don’t be afraid of adding a little structure.

Because human beings are like tomatoes.

Once they’re planted, you can choose to use a light, open cage to help them grow. Or you can leave them alone.

The ones without the cage structure will sprawl on the ground, right into the crawling path of the caterpillars and squirrels. And any fruit they produce has a higher chance of rotting on the ground.

But the ones in the cage—open enough that the light gets in, but strong enough to support their growth—grow upward, quickly, and bear beautiful, valuable fruit.

Just ask any gardener. Or the Chicago Cubs.

How can I help YOU? Email me now and let’s chat.

I also have hundreds of free tools here, plus my new guide, 3 Secret Ways to Switch Gears in Your Career is out now. Get it here.