Lesson from The Captain, Derek Jeter

Derek Jeter was on my mind a lot last week. All over social media, people were posting the replay of the famous “flip play” against the Oakland A’s in the playoffs, which happened fifteen years ago. Time flies, but I remember it like it was yesterday, just like many of his other October heroics.

This summer, at the 20th reunion of the 1996 Yankees, Jeter sat down with the rest of the Core Four, Mariano Rivera, Jorge Posada, and Andy Pettitte, in a discussion that was chronicled for The Players’ Tribune. The last line in the article, which came from Jeter, stuck with me:

“During my career, I never had to worry about you guys. I never had to question whether you were ready. I always knew you were prepared to play and you were going to work hard. And most importantly, I knew whether we won or lost meant just as much to you as it did to me.”

They were lucky to find a group of leaders who were all aligned to the common goal, and their mindset and expectations naturally spread throughout the clubhouse

It’s no different in business. I always say that I am lucky to have had the same business partner for the last fifteen years in Joe Sarno. During that time, we have had other partners and team members come and go, but Joe and I have always been aligned in how we conduct our business, and what’s important to us.

We have had members of our team, over the years, that weren’t on the same page. Whenever that was the case, the entire team struggled. We would have meetings to discuss how bad our team meetings were. We took time away from our clients and from business development to discuss internal issues, and we had a lot less fun.

Similarly, one of the top teams in our region had a chemistry problem years ago focused around one team member. He was working as hard, if not harder, than the rest of the team, but his partners felt he wasn’t collaborative. He ended up leaving the company, starting his own team, and both teams made more money because they were aligned and able to focus on business.

Joe has always stressed that you have to like and trust the guys you work with day-in and day-out. It’s not always easy to come by, but it’s truly the key to any great team or partnership.

Three years ago, we added a new member to our team, Matt Wassel. Matt quickly showed promise as a young broker, but more important to us, a willingness to be on our same page. He trusted us, was eager to be trained, and his addition has benefitted our team tremendously. This January, we are likely adding another team member. At this point, if we weren’t convinced that he would add value to the team, both with his skills and his attitude, we wouldn’t rock the boat.

Earlier this month, a close friend called me for some advice. He wanted to add someone to his team who had the ability to help his company tremendously, but he was worried about his character and how he would fit in with the other members of the team. He asked what I thought. I told him that he answered his own question.

In business, sometimes we win and lose every day. In that way, it’s not that dissimilar to baseball. Doing it with people who value the same things make the winning that much better and the losing a little less painful. The Core Four used that formula to win five World Series titles. I am trying to use that same formula for our team and am hoping that, starting in January, our core four will be similarly aligned.

We all can’t play for the Yankees, but that also may not be the best fit for everyone. If you are on a team and it’s working, figure out why so you can continue to thrive and possibly grow. If you are on a team and it’s NOT working, read Jeter’s quote again. Maybe the answers are all right there.