It’s never easy to say goodbye. The graceful and perfectly timed exit is an act mostly reserved for movie screens and potboiler novels. In the real world, most of us are pushed out the door many hours, days and years after we should have left by our own accord. Leaders can be especially susceptible to this most awkward of foibles.

Even if you’ve done a perfectly fine job, there comes a time when you have to cede your position to someone younger and more energetic. It’s not so much that you have failed, but that you risk tarnishing your many successful years of service with a few less than stellar years of mediocrity or worse: out and out failure.

The list of business and political leaders who have overstayed their welcome goes on for miles (Tony Blair, Fidel Castro, Hosni Mubarak, AIG’s Maurice Greenberg, Bear Stearn’s James Cayne, etc.) Yet there is one industry where we get to see leaders go from heroes to goats quicker than any other: Professional Athletics. A political or business leader might make a bad decision which leads to a problem or disaster a few months down the road, but when a 42 year old Willie Mays stumbles trying to catch routine fly balls during a nationally televised World Series game that a 23 year old Mays used to chase down effortlessly, the world gets to see his fall from grace in real time.

Recently most sports fans had the misfortune of watching Brett Favre stay a few years too long at the party. In Favre\’s case his denouement came as a result of a devastating, concussion-inducing and most likely life-shortening sack. This brutal exit is an over-the-top example of why all leaders must know when to say when. Yet it’s important to understand that very few careers end with such violent exclamation points.

In the past few days the New York Yankees’ Jorge Posada has been facing this very conundrum. After 16 amazing seasons (including 5 All-Star Game appearances, 5 Silver Slugger Awards and 4 World Championships) Jorge has nothing left to prove, he is a champion and according to most reports a gentleman’s gentleman. Unfortunatly his 17^th season has started horribly. His .165 batting average is the lowest in the league and this past weekend he actually removed himself from the starting line-up because he was slotted to hit 9^th, which in baseball circles is a slap in the face to anyone of Posada’s pedigree.

As I write, Posada is still soldering on but I can only imagine what is going through his mind. It’s moments like these where a leader is forced to make a decision that can affect not only how they are seen for years to come, but also the future success and/or failure of their organization. I do not envy Jorge Posada’s fast approaching choice. Despite all the difficulties and embarrassment of the past weekend, Jorge Posada still has the chance to walk away near the top and not only sustain his legacy but also give the current Yankee team a chance to succeed in the present and the future.

The bottom line is that proactive leadership is not only about getting things done; it’s also about sustainable and lasting success. And not just your own success but also about the success of those you lead. A true proactive leader is in many ways self-less. They know it’s not all about them. They want the best for those they lead and will do what it takes to guarantee a high level of future achievement.