🔒The leadership paradox

In June, I was able to join a delegation from Leadership Greater Hartford to the Association of Leadership Programs’ biennial conference in Tulsa, Oklahoma.

One of my many takeaways from this experience was a stronger resolve to think less about leaders themselves and more about those who are being led. Therein lies the problem, though, as leaders (whether in politics, sports, pop culture or business) are almost always faced with paradoxical — and at times even diametrically opposed — expectations established by the very people they are charged with leading.

Consider the following:

• People claim they want and need seasoned, experienced leaders; yet they are often dazzled by flashier new faces whose unorthodox ideas challenge tradition. (See the cast of presidential candidates in 2016 and 2020.)

• People often say they want their leaders to be “real human beings”; yet they project utter resentment when those very same leaders display real human flaws. (See the personal transgressions of William Jefferson Clinton.)

• People insist that their leaders “do what is right” and what is “best for the team”; yet those very same people can (and will) rake those very same leaders over the coals if they make an unpopular decision. (See the social media assault on New York Giants coach Ben McAdoo after he benched beloved quarterback Eli Manning.)

• And people want their leaders to use their pulpits to advocate for that in which they passionately believe; yet those same people will criticize those same leaders for attempting to impose their personal beliefs upon others. (See the recent political activism of Grammy award-winning singer Taylor Swift.)

The simplest explanation, of course, is that people are — by their very nature — both fickle and irrational, easily swayed by the whims and winds of the day.

As Aaron Sorkin so poignantly wrote in his screenplay “The American President,”: The masses “don’t drink the sand because they’re thirsty; they drink the sand because they don’t know the difference.” It is certainly the easiest way to justify the paradox of leadership … but it is not necessarily correct.

The real reason for this paradox is much more complicated and rooted in the structural tenets of sociology, political science and even biology. People unquestionably have an innate drive to survive and to succeed; but when coupled with the norms of our societal culture, that drive often manifests itself in the desire for both communal excellence and personal happiness.

Put simply: People aren’t fickle; they naturally articulate judgements that reinforce their own interests at any given time, some of which are consistent with the common good and some of which are not.

So we ask the question: Where does that leave those of us in positions of leadership? Are we forever condemned to oscillate among the paradoxical extremes expressed by the masses?

Like all things in life, there is clearly a balance that must exist between what we say and how we subsequently behave. But if you were to ask me — a leader myself — where that balance exists, the best I can do is quote Supreme Court Justice Potter Stewart’s legal definition of obscenity: “I know it when I see it.”

The leadership paradox is most certainly real, and acknowledging its existence is the first step toward helping navigate it. As long as we stay true to ourselves and remain focused on the needs of those whom we serve, the masses should be appeased … or so I hope.

Jason Jakubowski, president & CEO of Foodshare and chair of Leadership Greater Hartford’s board of directors, was awarded the Distinguished Leader Award by the Association of Leadership Programs in June 2019.