I put on Moneyball yesterday and was immediately struck by how relevant this story was, is, and will continue to to be long into the future. It’s a story of an underdog, a story of competition, and it relates to ALL of our industries, businesses, and methodologies in how we approach them.

Same As It Ever Was

“If we play like the Yankees in here, we’ll lose to the Yankees out there.”

Brad Pitt Playing Billy Beane in Moneyball

Faced with the insurmountable task of replacing their top three players, Beane realized he needed to do something different. Not only that, he had to do it on a team budget that rivaled the salaries of top players in the major leagues.

Moneyball, then, is the perfect movie for entrepreneurs. It’s a reminder of the importance to step away from “business as usual” and how important it can be to think outside the box, take cues from other industries, and take risks knowing full well that they may fail.

That quote by Billy Beane in the film can be found in an adapted form everywhere. For example, I recently finished The ONE Thing by Gary Keller, who states: “A different result requires doing something different.”

Similarly in No More Mr. Nice Guy, Dr. Robert Glover talks about how nice guys get frustrated when the things they are doing don’t go their way, so they just try harder doing the same things while hoping for a different result. But that never works.

Ask The Right Questions

This too has come up again and again, and it is the mark of a good leader: probing with questions.

When I was at BrandQuery, that was cornerstone to the exploratory client process. I imagine it continues to be this day. It was so integral to the process that the owner made it part of the company’s name. Questions were the way to get to the heart of what the client was hoping to achieve with any given project.

In my current role, we are working on a book in which the owner and author talks about how questions get to the heart of a home seller’s motivation, expectations, and desires. You can’t know their desired outcome if all you are doing is selling yourself. You have to ask questions and you have to listen.

And again we have it here in Moneyball: they were asking all the wrong questions. Yet it permeated everything in the game as witnessed in an early scene where Billy Beane asked his scouting team what problem they were facing. Not a single one of them could provide an adequate answer. Because they were not asking the right questions, they were chasing the wrong problems.

Adapt or Die

In order to enact change, to look at things differently, to adapt…well, that requires the courage to begin. And you cannot promote that courage without a sense of safety.

Creating a culture that allows a safe space to try something new and provides leniency and acceptance for failure will allow the company to adapt with much more agility. In the film, there were plenty of bottlenecks beginning with the scouting team as noted before and continuing with the coach, who resisted Billy’s efforts to try something new.

There were three pivotal moments in the film.

First was the decision to do things differently than they had always been done, and subsequent action taken on that decision. This was cemented when Billy hired Peter Brand to work the numbers and help him pick a team that could win.

Third was Billy’s realization that he couldn’t eliminate himself from the mix to see his vision though. As he and Peter began using numbers and data analysis at the game-by-game level, the team really started to win, and we saw camaraderie, morale, and life breathe back into the team.

Next was the implementation of the team he picked. Art Howe refused to play the lineup as Billy designed it, so he traded a handful of players including Pena who played First where Beane wanted Hatteburg, and Giambi who was presented as a bit of a toxic personality for the team. This forced Howe’s hand.

Failure Is The Best Way to Learn

I’ve heard this a few times about failure and about leadership. As a leader and/or entrepreneur, we have to create environments that promote risk in a healthy, collaborative way.

That means recognizing that failure is a monumental part of success.

Almost everyone fails at least a dozen times before seeing, reaching, or achieving the success they hoped for in the beginning. Norwegian folk-pop band Kings of Convenience sang about this in their song “Failure”

“Failure is always the best way to learn,
Retracing your steps until you know,
Have no fear your wounds will heal.”

“Failure” by Kings Of Convenience

At the end of Brene Brown’s Dare to Lead podcast featuring Charles Feltman titled Trust: Building, Maintaining, And Restoring It, Brown asks Feltman for a piece of leadership advice that’s so remarkable he just must share it with us.

Feltman replies, “Make the environment, make the relationships, make the team safe enough so that people can fail and learn, and fail and learn, and fail and learn.” 

But creating that sense of safety requires a foundation that supports it. It not only requires thought leaders and entrepreneurs to promote thinking differently, it requires those ideas to permeate throughout the organization.

“Baseball thinking is medieval. They are asking all the wrong questions. And if I say it to anybody, I’m ostracized. I’m a leper. So that’s why I’m cagey about this with you.”

Jonah Hill as Peter Brand in Moneyball

Brand recognized that there were fundamental issues within sports in how teams were managed, and saw that a different approach–one employing of mathematics and statistics–could create a winning team.

But it extended beyond just picking the team. It wasn’t enough.

Above I noted the third pivotal moment: drilling deeper into the numbers to statistically and strategically approach how the game was played not only on the team’s numbers as a whole, but how they stacked up next to the team they were playing.

This type of shift was previously unseen in baseball, and it led the Athletics to an incredible winning streak.

A Never Ending Story

The business, leadership, and teamwork lessons you can take from a story like Moneyball are truly never-ending. Years later, the lessons we can take from Moneyball continue remain relevant and are great reminders to promote a culture of change.

That’s why time and time again you see patterns in what thought leaders discuss: flexibility and adaptation, failing until you succeed by trying new things, digging deep to find the root problem and doing so by asking questions—and not just that, trying to find the right question to ask.

That’s why all those years ago, Jeff Vaughan of Vaughan Premier handed a copy of the movie to his entire management staff, of which I was a part.

Jeff had a mantra that I love and continue to live by and remind myself of to this day: We thrive at the intersection of chaos and innovation.

I could let loose and keep going, but I would just start talking in circles, so I’ll just leave it at this: 

In business, as entrepreneurs, as leaders, we must constantly be willing to seek outside opinions. We must constantly be reading (or listening to) new resources and literature. We must constantly be growing and changing and adapting ourselves so we can promote new ideas and have that trickle down to our team in a culture that thrives in change.

That will just help us on the path to success.