“It won’t end well,” stated an experienced headmaster to an aspiring leader. But it could begin and end better with a little insight on the matter. After all, “The credit belongs to the man who is actually in the arena.”

The effective Headmaster will provide thought, and organizational leadership in three primary arenas, each of equal importance: 1) as visionary leader, 2) as head teacher, and 3) as chief executive officer. As visionary because the organizational leader needs to look ahead to lead toward achievement of its highest ends. As head teacher because he (or she can be assumed throughout) runs an academy where teaching and learning great ideas is the paramount purpose, and head master by definition means head teacher, or the leader of the college of faculty. As chief executive officer, because the Headmaster is the sole report of the board of trustees responsible to fulfill academy ends, mission, or vision while assuring organizational integrity. The job description is a broad and exciting one because the headmaster is leading an organization that changes the lives that will influence the future, and everything rises and falls on leadership.

This work called The Headmaster does not presume to be the only view one could take of this calling in the sphere of education. It happens that I have spent much of my career in this vocation and intend to share some of my ideas on the requisite characteristics needed for success and its importance to the qualitative, and quantitative development of American education. Nor do I claim to fill up all the requirements. I doubt anyone will fill the requirements fully because no individual leader can be all things to all people. Rather someone aspiring to or already laboring as a headmaster needs to develop in each of the three major categories, while recognizing personal strengths and weaknesses.


Your idea about the model headmaster theory (one which a headmaster strives toward but may not achieve because no one is perfect) reminds me of two ideas in Cicero. In De Oratore, his masterpiece on the perfect orator, Cicero explains all the qualities of the active, civic orator. And in De Republica, he outlines the perfect politician. Both theories are about the ‘perfect’ person, not because Cicero thinks we all can be perfect, but the model of any theory must be perfect, so we have the highest goal in view, (this allows us to measure our progress as well!). I now think of Browning: Ah..but a man’s reach should exceed his grasp, or what’s a Heaven for?”

Daniel R. Fredrick, Ph.D.
American University of Sharjah

The wise leader will then surround himself with others that fill in the weaknesses to release the greatest effectiveness for all. I look for people who are better than me at the various parts of The Headmaster’s comprehensive job. Some leaders fear to retain people more talented than themselves. I love it because developing other leaders will contribute to a better future and working myself out of a job and moving on has always been part of the joy of life for me. I primarily look for those that like to operate the schools, and perform day-to-day business administration, since I thrive in the visionary, great ideas, and entrepreneurial aspects of the role and wilt when performing day-to-day functions as my primary duty. That said I know outstanding headmasters that flourish as day-to-day leaders that have adopted the vision of an already functioning school. For that person, with different proclivities delegation would take a different form.

Overcoming Objections

Allow me to overcome a few objections about The Headmaster’s role before introducing thoughts about each category in future articles.

Some will object that the trustees are the visionaries; and visionaries they should be applied as keepers of the organization’s mission or ends. However, The Headmaster is the visible leader, and primary proponent of the organizational vision, and therefore must see far ahead with the board to lead the school to success. Some would prefer a bureaucrat as headmaster; someone to care-take or make sure everyone is happy, and that the business operation is solvent. In this way complaints, are minimized, and no one experiences financial anxiety over the operation. While people like the trustees should not need to field complaints, or experience financial anxiety, unlike a caretaker, The Headmaster as visionary leader will lead an organization of excellence that maximizes achievement of the vision, and therefore maximizes satisfaction of all the various constituencies, while assuring solid business administration and organizational integrity. The key difference is that The Headmaster is first a leader then a manager. A leader can learn to manage but a manager that lacks the spark of leadership may never develop into a leader.

Recent publications imply that the role of the Headmaster has migrated toward CEO in the larger school, while head teacher duties are delegated to an academic dean. Some say The Headmaster is wasting valuable time when teaching or developing curriculum because there are CEO duties only he can perform. Certainly, in the larger school, delegation of responsibility is a necessary part of leadership and staff development. Yet, the excellent Headmaster will never allow himself to be relegated to managing from behind a desk. He must be out there leading from the front, promoting the organizational mission, while encouraging each constituency, and leading the way intellectually by grappling with the great ideas, in conversation with students, faculty, parents and beyond.

In any innovative idea-oriented industry, the CEO should be the most prominent leader. A quintessential example in the technology industry for a few decades was Steve Jobs, CEO of Apple. While some tech companies sell equipment, software and services, Mr. Jobs has a loftier vision as illustrated by a comment he made in persuading John Sculley, then President of PepsiCo, to become Apple’s CEO years ago. “Do you want to spend the rest of your life selling sugared water or do you want a chance to change the world?” The parallel is obvious. The Headmaster behind a desk may provide for a smoothly run operation, and happy constituencies, but changing the world for the better with great ideas takes visionary leadership.

Some desire a headmaster that serves as an amiable social administrator collaborating with all constituencies, and even evaluated based on how much these various constituencies like him. While the Headmaster must be winsome, his chief responsibility is leadership, and a leader is not liked all the time because he makes decisions for the long-term benefit of fulfilling organizational ends, not short-term decisions to placate someone’s particular desire. A leader makes difficult and sometimes-unpopular decisions for the greater good of striving to achieve organizational success by changing lives with great ideas. This vacation is worth the career risk.

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”  Excerpt from the speech “Citizenship in A Republic” delivered at the Sorbonne, in Paris, France on 23 April, 1910. Theodore Roosevelt