Introduction

Moneyball is an absolutely terrific film from 2011, with Brad Pitt portraying Billy Beane. Billy Beane was the General Manager for the Oakland A's for almost twenty years before being promoted to Executive Vice President of Operations.

This movie is rich with lessons around leadership!

Synopsis

Billy Beane is the General Manager of the Oakland A's, struggling to put together a winning team with only 30% of the money that big-market teams (Red Sox, Yankees) have at their disposal. Billy decides to go against the existing mindset of baseball by using sabermetrics (SABRmetrics?) to find undervalued players.

Critical scenes

Changing the game

Let's just say that Billy's pivot away from scout 'instinct' and to a more scientific numbers-based approach is met with very little enthusiasm at best, outright hostility at worst. Billy had to deal with irate fans, hostile sport-radio jockeys, obstinate coaching staff, and his own self doubt. All this time, he was singularly focused on what he felt was right, and best for his team.

Dealing with Eeyores

Billy is beset on all sides by naysayers and Eeyores (Winnie-the-Pooh reference, look it up), with the exception of the team owner. The most vocal critic is the head scout of the A's, Grady Fuson. The plan Billy executed generally sidelined the entire scouting staff, which came to a head in a scene where Grady and Billy go at it.

The scene demonstrates Billy's leadership. He gives Grady plenty of room to air his grievances, uninterrupted, trying to see if this is a Grady having a temporary fit or if it's something deeper. Grady eventually crossed the line, accusing Billy of 'getting back' at scouts because he (Billy) was such a flameout in the MLB, at which point Billy calmly told him how unscientific baseball scouting is, and that teams needed to "adapt or die". The scene ends with Grady saying "fuck you" to Billy, at which point Billy fires Grady and, in a reactionary mode, Billy promotes a twenty-something with no scouting skills the role of head scout.

The leadership example here is giving Grady plenty of time and space to get onboard with the plans, but didn't let him sabotage the plan. When Grady made it clear that he was not onboard, and had no intention on getting onboard, Billy had to take immediate action.

As an aside, the real Grady Fuson was actually on board with Billy's plan. Grady left the organization on good terms in 2001, moving to the Texas Rangers to be promoted to assistant GM.

Recognition

Near the end of the movie, after all is said and done, Billy is at Fenway Park. He is talking to the owner about the Red Sox (John Henry, played magnificently by Arliss Howard) and that team trying to win a World Series after a eighty-plus-year drought. I don't want to go into details in this scene since it would be major spoilers, but suffice to say John reminds Billy everything that was accomplished: Creating a playoff team that can compete at the same level as the Yankees, but at 25% of the salary. His actual quote was spot on:

For forty-one million, you built a playoff team.  You lost Damon, Giambi, Isringhausen, 
Pena and you won more games without them than you did with them. You won the exact same 
number of games that the Yankees won, but the Yankees spent one point four million per 
win and you paid two hundred and sixty thousand. I know you've taken it in the teeth 
out there, but the first guy through the wall. It always gets bloody, always. It's the 
threat of not just the way of doing business, but in their minds it's threatening the 
game. But really what it's threatening is their livelihoods, it's threatening their 
jobs, it's threatening the way that they do things. And every time that happens, 
whether it's the government or a way of doing business or whatever it is, the people 
are holding the reins, have their hands on the switch. They go bat shit crazy....

This bit from the scene always gives me chills, and it's absolutely true. When you are the first person through the wall, all you see is dust and all you taste is the blood in your mouth: You do not always see the accomplishments, and all that fills your ears are the lamentations of those losing control of the power. Getting recognition, even from the most unusual of sources, provides one a different perspective to clear the dust and wash out the blood.

The Lesson

It cannot be stated enough that when you're trying to change the game, you will NOT get everybody on board. No way. The advice here is to avoid the Eeyores if you are able to, but put your foot down when the Eeyore starts to sabotage your work. The larger the game change, the larger the population of Eeyores. There are three important items that Billy did during his process: The first two he did right away, the third one he had to learn:

• Keep his boss (Stephen Schott, played by the Activision Blizzard CEO Bobby Kotick) informed and on his side.
• Find as many like-minded leaders as possible, and keep them close. Any leader (manager, scouting team) who was not an ally was pushed out of his circle. He was not going allow his plans to be sidelined by a committee who doesn't share his vision. Unfortunately, his 'circle' was small, comprised of his assistant General Manager and eventually one of the more experienced ball players.
• Work with your team (not the Eeyores) to explain your vision, keep repeating the vision, and work with individuals to help them improve to achieve your vision.

It's the last point that Billy fell down on until late in the season (movie). He had the General Manager mindset that he should not interact with the team: He felt like he needed to appear above the fray. He was asking everybody to change, but did realize he needed to change as well. Once he started to communicate more with his team, specifically the planned changes on how they can individually contribute, he got greater buy in.

Individual Experience

When I started to develop an IaaS program, we had a lengthy, high-touch process to request a server. Going from initial request to final delivery would take up to three weeks. I'm not talking about physical servers, I'm talking three weeks for a virtual server. Lots of engineers involved, lots of requests, lots of errors. We were moving that time frame from three weeks to three hours or less, with zero human involvement: No blockers between the requestor and the delivery of the server. All the people who had their hand on the switch proceeded to freak out. Many engineers went back to their teams with a "this will never happen here" approach, with one engineer actually alined to the project! I had a talk with the director of that organization, reminding them of the goals of the organization and asking for a different engineer (which was assigned within days).

This took a while, a few years at least, to go from idea to delivery. But I kept the Eeyores away, held a close ring of people who were on board, and had a management stack that was 100% committed to what we were trying to accomplish.