Towards the end of the 2007 season, the New York Yankees were forced to come to terms with a glaring problem they couldn’t ignore any longer. Derek Jeter – the man who had become the face of their franchise since his debut in 1995 – was a defensive liability.

Next season, Jeter would turn 34 years old. He had won three straight Gold Gloves from 2004-2006, but the devil was in the details. In 2007, Jeter committed the most errors in a single season (18) since his 2000 season. He recorded negative Defensive Runs Saved (DRS) in all three of his Gold Glove seasons, adding a fourth in 2007 (-24). 

Jeter’s unique instincts and feel for the game often made people overlook his notorious defense, but 2007 made people within the organization really question if he was going to be a part of the Yankees infield going forward. In fact, everyone within the organization seemed to be on the same page.

No one had the courage to tell him.

General Manager (GM) Brian Cashman had been the man responsible for drafting Jeter back in 1995. His boss – George Steinbrenner – possessed an ice cold personality when it came to on field performance. You were either going to help the Yankees win, or he was going to find someone else that would. While coaches within the Yankees organization were too scared to tell Jeter about his defensive decline, Cashman was not. He felt constant pressure from Steinbrenner. He could not afford to have a liability at shortstop – even if that player was synonymous with the team itself.

When Cashman sat down with Jeter at the end of the season, he shared what everyone within the organization had known for years: If he didn’t improve his defense, they were going to have to move on from him at shortstop. Jeter was beside himself. Not because of the numbers, but because coaches he had trusted within the organization had not told him the truth. Instead, they knowingly withheld information that prevented him from addressing a glaring weakness in his game. Cashman was the first person who had the guts to tell him.

Now knowing this, Jeter switched up his offseason at the end of ’07 and changed trainers. He workouts were designed to help him gain the step he had lost over the years, focusing heavily on his speed, agility, and quickness. Two years later at 35 years old, Jeter had the best defensive season of his career. The Yankees won the World Series – his fifth and final one in pinstripes. 

Just imagine if Cashman didn’t tell Jeter what everyone else was afraid to.

…

My message to coaches is much easier said than done. Great players – like Jeter – are just like the rest of us: They have flaws. Most of us are taught to ignore these flaws in favor of the things they do exceptionally well. In some cases, this works (e.g. applying the DH). We can design their game around what they don’t do well, until what they don’t do well becomes an impediment to their game.   

Enter Jeter.

Jeter’s aura and iconic status throughout New York made him an intimidating presence. You don’t want to deliver bad news to one of the greatest Yankees shortstops of all time. You’d rather sit in the background because most people don’t take feedback well. Here’s the thing: Jeter isn’t like most people. He is completely and obsessively focused on becoming the best player possible. He wants – and needs – hard coaching. If you shared important information with him about a glaring weakness in his game, you wouldn’t lose his trust. You would gain it. It takes a lot of courage to tell the face of your franchise he’s hurting the team in an area he takes a lot of pride in. 

Cashman’s conversation with Jeter didn’t sting because it brought him to grips with reality. It stung because coaches he trusted had denied him the opportunity to become the best version of himself on the field. If we want to be effective in our interventions with our players, we cannot make this mistake. Tough conversations aren’t a part of the job. They are the job. You only have one window to deliver the right conversation at the right moment in time. You never get that window back once it passes.

The margin for error in this game is razor thin. Most careers are over as soon as they started. If you have the opportunity to extend one because you have information they do not, you cannot and should not ever pass this chance up. What they do with your information is up to them, but they can’t improve what they aren’t aware of.

Regret has never stepped foot where courage has walked.