The Puzzle: Blog

Such musings often take place during the holidays, when one has more unscheduled time and when family and friends engage about what’s next. I still recall the recommendation from a young student who said, “Why don’t you become a lawyer? You could make so much more money.”

When thinking about becoming a school Head, there are many factors to consider. The first and perhaps most important question to ask is: Do I know what the job entails and am I ready to take on its responsibilities? Hiding right behind that question is a second one:  Do the challenges and demands of the job work with my family/personal circumstances?

Next, spend some time weighing the perceived pluses and minuses of new responsibilities. A distinct tone of weight and stress characterizes  much of the testimony about headship—a telling indicator of the many challenges and complications of the job. In some ways, it often sounds as though leadership is tough, demanding, and painful at times, and that anyone seeking it should be ready for the worst. Most long-term Heads of school have a collection of “war stories.” The problem with starting your contemplation of leadership with the negative is that the positive, joyful parts of the job can seem to pale in comparison.

So many aspects of the work bring satisfaction and a sense of accomplishment and should get their due in your deliberations. All of us want to have meaning and purpose in our lives, and those who have chosen education as a profession are especially captured by that aspect of the work. As a Head of School, you set institutional direction, watch your colleagues flourish, see students excel or overcome in ways not imagined, and work toward the continuation of the school you are entrusted to lead. On a good day, you may even have the pleasure of being invited to read to the kindergarten class! These are high-altitude rewards that last.

For example, spearheading the effort to alter an iconic building, so it could provide a beautiful space to house an entire school community, was worth the many hours of work building consensus among faculty, staff, students, trustees, alums, architects, builders, and historical preservation groups. In spite of the demanding job working with so many disparate interests, this project remains one of the most satisfying professional accomplishments of my career as a school Head.

Another aspect of the “so you want to be a school Head” consideration is that at some point you will complete the list of pros and cons and need to “cross the bridge,” not completely knowing what lies on the other side. I found this decision-making process similar to the process I used solving the problems I encountered as a school Head.  Incomplete or competing information, differing views from community members, and uncertainty of the outcomes was often the context of my work. I believe that one of the most important qualities that successful school Heads need is the ability to listen deeply, then let their instincts and values lead the way. Quakers write and talk about the power of silence and the arrival of the light—a  wonderful image of how decision-making often occurs.

One last thought about considering a headship is that some young leaders in independent education want the job right out of the gate, and others develop an interest after experience and reflection. In my consulting work, I am often struck by the approach of some who say they don’t know if they really want the top job. In my view, that doubt reflects a fundamental self-awareness that is essential to great leadership.  Many Heads I have known are Collins’ Level 5 Leaders: humble, reflective, and motivated almost completely by the joy of helping others succeed. What could be a better life? Good luck with your thinking.

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

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