03/02/2015 by Jake Dresden |

What Constitutes Good School Leadership?

As I look back over a 44-year career in independent education, 18 of which were spent as Head of School, and now more than five years as a search consultant for schools, I find much has changed and much has stayed the same.

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One worrisome change I’ve noticed from the front lines while helping Boards of Trustees find new leadership is a deep shift in the assumptions about what makes a successful and effective leader of an independent school.

It goes without saying that leadership has been studied about as much as Napoleon or Lincoln in the last generation. Whole forests have been devoured by “leadership literature,” much of which is devoted to a corporate vision of success. From Harvard Business School on down, article after article has cataloged the reason CEO X failed and CEO Y succeeded. In my opinion, these cases more often reflect the natural process of some successes and some failures than they identify some magic that one leader has and another doesn’t. While this literature is rarely directly transferable to the non-profit sector — and especially to independent schools — Boards are increasingly populated by individuals who imagine that schools and corporations are only minimally different. It is here that I would like to make my case for leadership.

Rooted in Quaker education and now serving on a Quaker school Board, I am deeply aware of and committed to the idea that leadership is service — and that it can only thrive in its best form when tied inexorably to mission. Why? Because to be the best leader, there must be a deep and emotional attachment to the mission one serves, not merely to the successful execution of the management goals set by the Board. As David Gergen’s course on leadership at Harvard’s Kennedy School of Government proposes, there are two journeys every leader must take: the inner one and the outer one. I suggest that the latter journey is filled mostly with skills that can be learned, while the former is based on one’s character, values, and courage.

Therefore, what should independent school Boards seek in their leaders? From where I sit, the key elements of a strong school leader include strength of vision, strength of character, tolerance for ambiguity, oral and written eloquence, and authenticity. None of these show up explicitly on a CV; rather, they are discoverable by direct and repeated contact with candidates. The tilt toward management skills and “external” experience (admissions, finances, and fund-raising) misses the point about leadership. Leadership is about character, not perfection; it is about the courage of one’s convictions, not the impressiveness of one’s “skill set.”

As one trustee on a search committee recently remarked, “How do you know when you have the right person?” I suggested three things:

  1. Stay focused on the person, not the credentials.
  2. Trust your judgment.
  3. Envision the person in a complicated, contentious situation. How would s/he handle it?

It is in the difficult times that leadership trumps management, and that’s when independent schools need their leaders most. At the end of the day, despite the volumes of research that have been expended on analyzing leadership, it is still an art form, not defined by a one-size fits all approach. That, after all, is the beauty of leadership.

Jake Dresden is a Senior Search Consultant with Carney, Sandoe & Associates.  Contact Jake at jake.dresden@carneysandoe.com


Image credit: Microsoft

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