“Hard work may not always result in success, but it will never result in regret.” — Billy Beane, Moneyball

I love a good baseball movie. If a movie strikes a deep enough chord, I will watch it again and again. Films like Field of Dreams, For Love of the Game, and 61* all fall into that category. I still watch The Sandlot at least once or twice a year. The Rookie is still a staple every spring. On a lazy Saturday, I can stream through every episode of Baseball, the 1994 documentary series from Ken Burns. So, when I found Moneyball one Saturday in the rack of dollar DVDs at the Iraqi “Blue Dome” market on FOB Union III in 2012, it was an easy choice.

Later that night—after some fine dining in the contract mess hall, a battle update brief, and cigars on the roof of former Baath Party headquarters—I returned to my CHU, slipped the DVD into my laptop computer, and prepared to take in yet another evening of cinematic bliss on a 15” LCD screen. I wasn’t disappointed. In fact, the following morning, I watched it again. If the movie was this good, then Michael Lewis’s book had to be even better. I purchased the Kindle edition and downloaded it to my iPad and read it cover-to-cover in a day. It was that good.

Moneyball – More Than Baseball

Published in 2003, Moneyball: The Art of Winning an Unfair Game recounts the story of Oakland A’s general manager Billy Beane’s efforts to rebuild the team following the 2001 season. With one of the lowest budgets in Major League Baseball, Beane needed to break tradition—and the status quo—to assemble a competitive team. His use of sabermetric research transformed baseball operations and in the process the Oakland A’s.

Against all odds, Billy Beane—a failed professional baseball player with a high school education—found success where few saw even remote possibilities. But Moneyball is more than a baseball book. At its core, Moneyball is about leadership, about perseverance, and about adaptation. Lewis’s particular brand of wisdom is rooted in the strength of his writing, and the lessons he shares underscore the challenges of leadership in a changing world.

Small Sampling of Moneyball Leadership Lessons

The ten quotes that follow are only a small sample of what Moneyball offers, but they are both noteworthy and relevant.

  1. “Managers tend to pick a strategy that is the least likely to fail, rather than to pick a strategy that is most efficient. The pain of looking bad is worse than the gain of making the best move.” Too often, leaders are so afraid to fail that they make safe choices that prevent them from achieving anything more than mediocrity. Success is a path paved with risk; learn to embrace that risk and anything is possible.
  2. “Every form of strength covers one weakness and creates another, and therefore every form of strength is also a form of weakness and every weakness a strength.” This sounds a lot like Sun Tzu, if the Chinese military theorist had managed a professional baseball team. But the wisdom can’t be denied: what appears to be a strength on the surface is likely masking a weakness. Find it. Exploit it.
  3. “What begins as a failure of the imagination ends as a market inefficiency: when you rule out an entire class of people from doing a job simply by their appearance, you are less likely to find the best person for the job.” Leaders who surround themselves with people who look, think, and act like them are only successful at building echo chambers. A little diversity goes a long way. Just do it.
  4. “People in both fields operate with beliefs and biases. To the extent you can eliminate both and replace them with data, you gain a clear advantage.” Data provides a clearer picture than opinions, which are too often tainted by any number of cognitive biases. Facts, especially facts supported by data, matter.
  5. “If you challenge conventional wisdom, you will find ways to do things much better than they are currently done.” Nothing dooms organizational culture quite like a leader without imagination. Don’t feel obligated to do things the same way they’ve always been done.
  6. “No matter how successful you are, change is always good. There can never be a status quo.” The status quo is a cul-de-sac where good ideas are lured in and slowly strangled to death. Adapt or die. Choose your weapon; if you’re not willing to change, the world is going to change without you. It’s that simple.
  7. “Anti-intellectual resentment is common in all of American life and it has many diverse expressions.” Anti-intellectualism is a fact of life in a lot of professions, and the profession of arms is no exception. It’s rooted in experiential bias, where experience is valued over perceived “bookishness.” Give the smart kid a chance, and they might just surprise you.
  8. “If you’ve got a dozen pitchers, you need to speak 12 different languages.” Teams are built from a collection of individuals, and each individual is unique in their own way. Any good approach to leadership accounts for this; that’s why there is no one-size-fits-all approach that drives success.
  9. “It is the nature of being the general manager of a baseball team that you have to remain on familiar terms with people you are continually trying to screw.” Friends may come and go, but enemies are forever. As leaders, treating people equally and fairly is critical. You don’t want to build a list of people who wish you ill. That tends to catch up with you over time, like Karma.
  10. “The pleasure of rooting for Goliath is that you can expect to win. The pleasure of rooting for David is that, while you don’t know what to expect, you stand at least a chance of being inspired.” Everybody loves an underdog because the underdog inspires us to believe in what might be possible. Set a vision and pursue it. You might not achieve that vision, but you’ll be better for the effort, and so will those around you.

It All Comes Down to Leadership

Moneyball is about believing in yourself, your team, and what you can achieve together. It’s about not being afraid to challenge the status quo. It’s about the necessity of adaptation. It’s about leadership.

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Steve Leonard is a former senior military strategist and the creative force behind the defense microblog, Doctrine Man!!. A career writer and speaker with a passion for developing and mentoring the next generation of thought leaders, he is a senior fellow at the Modern War Institute; the co-founder of the national security blog, Divergent Options, and the podcast, The Smell of Victory; co-founder and board member of the Military Writers Guild; and a member of the editorial review board of the Arthur D. Simons Center’s Interagency Journal. He is the author of five books, numerous professional articles, countless blog posts, and is a prolific military cartoonist.