How to Disappoint People: A Lesson in Leadership

There’s a saying regarding sports coaches along the lines of, “If you’re coaching for the stands, you’ll soon be sitting with them.” The point is that while sports teams are ultimately supported by their fan base, the fan base is often wholly ignorant regarding how to coach or run a team. Passion should never be confused for competence, which means coaches who strategize based on the capricious whims of a rabid fan base will likely be unsuccessful in performing the job for which they were hired.

I believe that anyone who serves in a leadership capacity will inevitably disappoint someone among the people the leaders is supposed to be serving. I do not only means in terms of making the same sort of mistakes all humans do, but leadership requires making decisions and as Alfred Einstein said, “What is right is not always popular and what is popular is not always right.” But while decision making is an obvious component of leadership, an equally important yet often ignored requirement of leadership is managing the consequences of those decisions. How does a leader make difficult decisions without fomenting partisanship or resentment?

One common approach is “damage control,” which focuses on the fallout after the fact. Depending on the situation and individuals, leaders may attempt to mollify the disappointed or the leader can ignore them entirely focusing exclusively on the new direction, or even use the opportunity to purge the constituency of malcontents. Other tactics are preventative, taking place during or even before the decision-making process. For example, leaders can solicit input or incorporate representative interests along the way, such that the ultimate decision is formed by consensus.

All strategies have one crucial element in common: the rejection of an idea does not imply the rejection of a person.

I found in my own experience as a pulpit rabbi that individuals were more tolerant of disagreements when there was a personal relationship beyond any specific issue. Regular normal interactions reinforced the idea the rabbi and the community cared about the individual for who they were. When a sincere relationship is developed and maintained over time, the inevitable disappointments of decisions, while unpleasant, do not have to create resentments, divisions, or schisms. Any subsequent efforts to achieve equanimity would therefore not be “strategies” for keeping the peace, as much as simply demonstrating care for someone else’s well-being.

Pleasing everyone all of the time is an impossible task which good leaders would not even try to attempt, but the better leaders will know how to preempt most dissonance and discord through the regular maintenance of individual relationships. Of course, demonstrating genuine concern requires regular commitment and effort sustained over time. Those leaders who are unwilling or unable to accept this responsibility do no service by remaining in leadership positions for which they lack a crucial qualification.

While coaches do not have to satisfy the fanbase’s expectations, they also cannot hold the fans in contempt. This is in part why coaches speak to the media on a regular basis, explaining their decisions even after a tough and disappointing loss. Coaches who ignore the fanbase entirely, find themselves in the stands along with those who tried to appeal to their every whim.

Unpopular coaches can be run out of town while well-loved coaches can survive losing seasons. Similarly, leaders who continuously demonstrate they care about their constituents will have more latitude for disappointment than those who maintain a relationship of detachment.

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