This article describes two well-known executives who changed strategic contexts: one used patterns and analogies well and was successful; the other didn’t. First we will examine the experience of Rick Pitino – an outstanding college basketball coach – who struggled with coaching in the NBA. Then we will examine how Billy Beane of the Oakland A’s used creative desperation and a healthy skepticism to rethink his managerial approach with the Moneyball-era Oakland A’s baseball team.

Rick Pitino: Patterns for College Strategy Do Not Translate to the NBA

As a college coach, Pitino had a won-loss record of 371-137, as of 1997, and won a national championship with the University of Kentucky. Pitino agreed to move to the professional ranks to become the GM and coach of the Boston Celtics. This move created a great deal of excitement for the Boston fans. Unfortunately all involved, the excitement and optimism turned to anger when the team failed to perform to expectations. With a record of 102-146, Pitino left to return to the college ranks midway through his third season, hugely unpopular.

What went wrong?  How could this great strategist fail?  In an article titled, “Lessons Learned (and Forgotten) from Celtics’ Failed Rick Pitino Experiment,” Grant Hughes writes,

“Pitino’s coaching style, just like the persona he employed in interviews, was very much “Rick-centric.” On the court, that meant he had to win on his own terms. The full-court presses and mass substitutions that led to so much success in college were going to define his Celtics teams, consequences be damned. Even when it became clear that the desired results of Pitino’s preferred style—forced turnovers, a fast pace, general chaos—weren’t leading to wins, the coach stuck stubbornly to his guns.

Hughes points out this key to success in the NBA: Players dictate strategy—not the other way around.  Antione Winfield, who played for Pitino at Kentucky and later at Boston reinforces the idea of patterning actions around players, observed in a different interview:

“What I noticed playing for Coach (Pitino) at that time, I think you have to be patient. I think if you look at Rick Pitino and what he did in that era, he traded probably thirty guys. “He’d sign guys and trade them right away. His patience level was so low. You have to be patient and you have to build something. You have to start with one or two guys and kind of build around them, and that’s a lot of things college coaches don’t want to do because they’re so used to winning at the collegiate level, at such a high level. When they’re winning 85, 86, 87 percent of their games, and then you get to the NBA level and it’s not the same.”

From a strategic thinking perspective, it seems like the problems are rooted in the patterns and context: basketball is different at the college level and at the professional level. The learning is to develop a sensitivity for patterns and context. Pitino perhaps suffered from what Gary Klein calls “passive stance” or what others call frame blindness.

The Coach’s Learning

Gary Washburn, writer for the Boston Globe interviewed Pitino. Looking back on the experience, Pitino says,

“The [fact of the] matter is I didn’t do a good enough job as an executive. It also taught me about wearing a lot of hats, focusing on what you can do. It was a class organization. They treated me great. I [had] nothing but great things to say about it when Brad [Stevens] got the job. It’s just that it didn’t work out for me, but it did work out for me because without the Celtics, I wouldn’t have learned all about failure and all about humility.”

Gary Washburn, offers this observation in the same article:

It taught Pitino he is better at convincing parents in a rural Kentucky home to allow their child to start his next phase of life at Louisville than crossing his fingers for good luck in the NBA draft lottery.

Billy Beane: Reinvents Himself, His Organization, and His Industry

Billy Beane, General Manager of professional baseball’s Oakland A’s, is now well known from the book and movie, Moneyball.  As a player, Beane played in the majors for several years with different teams, finally spending more time in the minor leagues than he cared for.  He chose to end his playing career in 1990 to take a job as an advance scout. In 1997, he was promoted to General Manager, taking over from Sandy Alderson. Using sabermetrics techniques, the team made baseball’s playoffs despite one of the lowest payrolls in the game. Beane completely reversed traditional wisdom about how to build a team, coming to the conclusion that scouts had no idea of what they were talking about, and looking for new statistically-based measures of productivity.

Beane was successful in part because he changed his own personal patterns. Says Sandy Alderson, who was the A’s General Manager and brought Beane into the organization, says in the Michael Lewis’ book, Moneyball: The Art of Winning an Unfair Game,

“What Billy figured out at some point was that he wanted to be more like me than like Jose Canseco.”  Addressing Beane’s change of mindset and patterns, Alderson said, “Billy shed every one of his player-type prejudices and adapted. Whereas most of the people like him would have said, ‘that’s not the way we did it when I played.

It’s instructive to note Beane’s own perspective,

“If baseball’s all you can do and you know that’s all you can do, it breed in you a certain creative desperation.”

As a concluding thought, it’s rather interesting that both men suffered a humiliation.  Beane’s was that of a player struggling in the major leagues, and being relegated to the rougher life of an aging minor-league player. Beane’s marriage also broke up at the same time he concluded his playing career. Pitino’s quote on learning humility from his Boston experience shows growth, and perhaps has helped him be more strategic as a person and a coach in his return to college ranks.

As a strategic thinker, you must have a sensitivity to patterns and context.  Too, perhaps much of journey to become more competent in thinking strategically might be in the way that you learn – and bounce back – from failures. Do you agree?