Rewriting the Strategic Playbook

Billy Beane, Moneyball, & the $64,000 Question

I sort of represented that entrenched thinking in some respect, because I was the guy who came up in the business – a business that was 150 years old – as a former player. Quite frankly, I had a great mentor, a gentleman who didn’t come up in the industry, in Sandy Alderson.

When I hired, I made sure I looked outside at somebody who didn’t have the experience bias with my first, and maybe even one of the best hires I ever had was Paul DePodesta, who was a Harvard Econ major, didn’t play sports, and really, was able to come in and look at things with an eye that wasn’t biased.¹

In 2002, Billy Beane, the then general manager of the Oakland Athletics, found himself in a high stakes battle against the financial titans of Major League Baseball. Despite Beane having one of the lowest payrolls in the league, his vision for success wasn’t bound by traditional baseball wisdom that focused on costly players. Beane recognized that vision is not enough when one seeks success. He realized that he needed to turn to a radical strategy based on data, analytics, and a deeper understanding of what truly drives winning. His approach became known as Moneyball, and it transformed not only the A’s but also the entire way so many now think about sports strategy.

What Beane's story teaches us is that if you want to transform vision into a reality it is not just about having the right ideas. You have to possess a bold strategy and the necessary tools to execute that strategy. When pursuing success in any organization, as in baseball, this accomplishment hinges on how well you can apply strategy to make your vision actionable, sustainable, and ultimately, enduring.

This is the second post in a six-part series discussing the elements of leadership outlined in Unpacking Leadership.

A Blueprint for Leadership

A postmortem conducted on any successful organization will surely reveal that they all started with a vision: a clear, compelling picture of what the future could look like. But a vision, or a good idea alone, is never enough. Bringing a vision to life, requires a clear and actionable strategy. It is the strategy that breaks down the bigger picture into manageable chunks, defining how each entity or individual can contribute to an overarching goal. While vision is about the end goal, strategy provides the actionable steps that get you there. Strategy is the blueprint leaders need to translate aspirations into tangible results.

So how do you develop a strategy that not only guides an organization toward its long-term vision but can also adapt to shifting circumstances and fosters collaboration among team members? You follow these simple guidelines:

Have a Vision that Informs Success

Without a vision, a strategy would be like embarking on a road trip without a destination in mind—it’s hard to know where you’re going or how to get there. It is the vision that provides the NorthStar, the direction, the purpose, or the inspiring goal that an entire organization can galvanize behind.

Beane’s vision was simple: build a winning baseball team despite the financial constraints of the Oakland Athletics. His vision was not focused on competing with other teams on sheer talent or spending power. He instead focused on finding undervalued players who could contribute in unconventional ways. Once a vision is crafted, the next step is to break it down into actionable components.

Breaking it all Down

Dissecting a vision into smaller components is necessary to build a strategy. By taking a broad, long-term goal (your vision) and dividing it into manageable and actionable steps (the objectives), leaders can establish short-term goals and immediate actions that can be achieved within months to a year. These short-term objectives lead to bigger outcomes, sometimes that can span many months or over several years, which in time lead to achieving the greater vision.

Rather than relying on what was considered traditional scouting methods based on intuition and experience, Beane turned to data analytics to identify those overlooked players who were statistically undervalued. He focused on the on-base percentages of players rather than traditional metrics like batting averages. After all, a team cannot score if the players never get on-base.

Beane's strategy broke down his larger goal into actionable steps: find players who could perform in ways that others overlooked and then assemble a team player by player around the data.

Foster Teamwork & Collaboration

A bold strategy can never be developed alone. It requires an inclusive environment that fosters diverse perspectives, brainstorming, debate, and discussion.

Steve Jobs worked with several key individuals - Steve Wozniak, Jony Ive, Tim Cook to name a few - to shape what we know as the Apple strategy today. General Dwight D. Eisenhower worked with a number of key advisors – George C. Marshall, Douglas MacArthur, and W. Averell Harriman - to develop his own strategies during World War II.

While it is the leader that sets the vision, establishing and advancing a strategy requires key team members. It is these same members that will be called upon to carry out their part in advancing the strategy.

Coach Beane does not execute his strategy alone. He instead enlists the help of Peter Brand, a young economist who understands the power of data. Together they work to convince the other scouts and team members to buy into their vision. Their collaboration is critical. While Beane’s vision might be fascinating, it is the teamwork that allows him to implement the strategy effectively.

Ensure Flexibility and Adaptability

No strategy is set in stone. As we write this, we cannot help but think of the classic Mike Tyson quote, ‘Everybody has a plan until they get punched in the mouth.” What he was describing is that no matter how much we plan or prepare for something, there will be unexpected challenges and setbacks that will throw everything of course.

The same goes for a leader developing a strategy. While the end goal remains unchanged, the road to get there can take unexpected turns due to both internal and external forces. For Tyson, it was a literal punch to the face, to the organizational leader the punches come in many different shapes and sizes.

Flexibility does not mean abandoning a vision, it instead means it is critical for leaders to be capable of responding to new opportunities and challenges to accomplish the long-term vision even within a changing landscape.

Throughout Moneyball, Beane faced resistance from within the organization and players themselves. Despite this, he adapted his approach to overcome obstacles. He tweaked the roster and adjusted his strategy. He remained flexible and open to modifying his approach in response to the changing circumstances.

Mentor and Measure: Adjust where Needed

Once a strategy is in place it needs to be “relentlessly followed up” upon and monitored for progress and setbacks. Regular check-ins with those responsible for accomplishing key objectives on established timelines are crucial to help ensure everyone is aligned and working toward the same purpose. Sometimes that requires leaders to coach those who may not fully understand that advancing strategy essentially comes down to measuring “who does what, by when.” Of course, in the same vein, keeping track of milestones while celebrating achievements go along the way toward building and maintaining momentum.

The true test of Beane’s strategy came in the form of his execution. He did not just build a team on paper; he executed it on the field. He identified undervalued players, placed them into the right positions, and then measured their performance on the field. A leader can have the most detailed of strategies, but if they are not executed, they are meaningless.

Set the Roadmap

A strategy cannot just reside in the leader’s head or on in their office. It has to be communicated loudly and clearly throughout the organization. Each component of the organization should understand how their specific contributions align with the broader goals. In larger organizations, each command level should have their own strategic plans that are informed, influenced, and aligned to the overall leader’s strategic plan.

Beane’s strategy was not just about winning baseball games. His strategy was about changing the way his entire team looked at value. From scouts, coaches, and his players, this required each component of his team to understand his approach toward disrupting traditional baseball thinking. His strategy may not result in an immediate World Series win, but it surely changed the future of the game.

Conclusion

Strategy is the key to attaining a leader’s vision. Strategy breaks down the larger objectives into actionable steps, promotes collaboration, and ensures that everyone is aligned and focused on the same outcomes.

In Moneyball, Billy Beane demonstrated that a great vision isn’t enough—it needs to be supported by a bold. clear, and well-executed strategy. Beane’s ability to break down a big idea into specific, actionable steps, innovate in the face of resistance, and execute with precision is a perfect model for leaders emulate when looking to turn vision into reality.

Just as Beane did with the Oakland Athletics, leaders can transform their organizations by thinking strategically, using data to drive decisions, and embracing collaboration. By breaking down a vision into tangible, actionable steps and being willing to adapt, leaders can achieve success even in the most challenging circumstances.

Sometimes strategy can be deceptively simple but obscured from view by the camouflage of overthinking. In Beane’s case, the strategy he needed was hidden inside the answer to the “$64,000 Question”: Why do you think they call it BASE-Ball?

So, when developing your strategy, channel your inner Billy Beane. In the end, you’ll be the one rewriting the playbook.

1. Billy Beane on Making Better Decisions, Challenging Entrenched Thinking, and Avoiding Biases, published by FS, available at https://fs.blog/billy-beane-making-better-decisions/, accessed December 10, 2024.