Have you ever been challenged to “be more strategic?”  Have you ever wondered what this ability actually means? If you were asked to give an example of someone being strategic could you do it?

People who want to learn to be more strategic need to know what it actually looks like. The problem is that most examples of being strategic are written in business case studies. While the case studies can be helpful they are always in hindsight and paint an unrealistic and overly simplistic picture.  They focus mostly on what the strategy was and it’s success, leaving out the behaviors, setting, and context that often go along with it. The human story of leadership and courage amidst ambiguity and adversity gets lost.

So I turned to Hollywood and asked myself what is the best movie showing someone “being strategic”?

MoneyBall.  If you want an up close, behind the scenes look at someone being strategic, watch this movie.  If you haven’t seen the movie here is a synopsis of the plot as the rest of this article will assume you are familiar with the story.

In my opinion, there are 4  main characteristics of “being strategic.”

  1. Seeing the Big Picture – prioritizing the longer term, broad, long-range approach to problem-solving.  Aligning tactical decisions with strategy, focusing on what is important and not what is urgent
  2. Challenging the Status Quo – having the courage to face conventional wisdom, face criticism and hold one’s ground
  3. Being Externally Oriented and Resourceful – leaving the familiar, and being open to new ways of thinking, listening to divergent opinions, exposing oneself to new ideas and approaches
  4. Cutting Through the Clutter – finding patterns and synthesizing information, finding a way forward amidst complexity and ambiguity, asking questions that matter.

Seeing the Big Picture (1) and Challenging the Status Quo (2)

Early in the movie Billy Bean (played by Brad Pitt)  addresses his team of talent scouts, “…we’re talking like it’s business as usual and it’s not.”  Billy asks the group:  “what’s the problem?”   The scouts sitting around the table perceive the issue tactically, “we need to replace three key players in our line-up.”  Instead, Billy sees the problem strategically, “we’re playing an unfair game.  There are rich teams, then there are poor teams…and then there’s 50 feet of crap, and then there is us. It’s an unfair game…We’ve go to think differently.”  The scene depicts Billy both challenging the status quo and trying to solve a problem by looking at the bigger picture.

It’s not easy to challenge the status quo.  You will get resistance.  People’s jobs and sense of identity may feel threatened by change.  Check out this scene between Billy and the head talent scout.  Billy takes a barrage of sometimes personal attacks.  His most ardent defense is “adapt or die.”

Being Externally Oriented and Resourceful (3)

During a visit to another baseball team in Cleveland, Billy comes across a meek, young statistician named Peter Grant who convinces Billy that baseball teams don’t understand how to win games.  “Baseball thinking is medieval.  They are asking all the wrong questions…Full disclosure I think it is a good thing that you got Daimon off of your payroll.  It opens up all kinds of interesting possibilities.”

Billy asks Peter about his background and is tickled when he learns that Peter got a degree from Yale in economics.  This scene demonstrates Billy’s openness to external ideas, even from unconventional sources such as economics.  It’s not lost on me that this discovery comes when he is away from this office conversing in the parking garage in Cleveland Ohio.  This is what is mean by “being externally oriented and resourceful.”  The answers to your problems are not to be found in the familiar.

Cutting Through the Clutter (4)

Peter shows Billy that the managers of baseball are unable to see the big picture and make hiring decisions based on unuseful biases.  In the following scene, Peter cuts through the clutter and boils success for the team to one number, the “on base percentage” and instructs Billy to make hiring decisions based on how often they get on base.   The point here is not to get lost in the data but to determine what the data is telling you and move forward.

Despite the fact that Peter shows Billy a host of compelling data and charts it’s Billy’s job to pull the trigger and make the hard decision.  What Peter is able to do that is key is to look at the same data and ask different questions, questions that matter and then connect the dots.  From the data emerges information and from information comes insight.

Final Thoughts

The purpose of this blog post is to help people develop greater strategic abilities.  The intent is to call out specific behaviors that you and anyone can begin to cultivate.   If you want to become more strategic then I suggest you  develop habits to:

  1. See the Big Picture
  2. Challenge the Status Quo
  3. Be Externally Oriented and Resourceful
  4. Cut Through the Clutter

The A’s didn’t get far in the post season,  despite ending with a winning record, leading their division (AL West) and breaking the record for most consecutive wins (20).   Billy’s winning strategy wasn’t enough.  As a leader, he was imperfect, and in my opinion, missed some key opportunities to bring people along with him.  His disregard for team cohesion limited the A’s ability to realize their potential.   In one scene, Art Howe, the team manager, brings up that his contract is due to expire and it is limiting Howe’s ability to remain committed to the team.  Billy quickly dismissed his concern.   Later in the movie, in an attempt to coerce Howe to commit to the strategy Billy trade’s Peña, the starting first baseman. The point is that Billy’s inability to galvanize Howe’s commitment cost Billy his star player, Peña.  Who knows what contribution Peña could have made to the post season?  The movie portrays Billy’s action as heroic, but the way I see it Billy is bullying Art Howe because he is unable and unwilling to earn his commitment.

In fact, throughout the movie Billy was aloof from the team, refusing to travel with the team, nor attend home games. When discussing strategy he gives Peter a dose of bad advice (in my opinion),  “it’s a problem, that you think we need to explain ourselves, we don’t.”

It’s a trap when leaders think that strategic brilliance alone is sufficient.  It is not.   To reach success, a leader must get people to commit themselves, along with their energy and talents to the strategy.  A strategy may come from the brain but people follow with their heart.