It was in "The Wizard of Oz" that I first heard the Wizard say, "Now that's a horse of a different color." Indeed, the differences and problems of the head administrator or head principal designation weaken a school so much and unless corrected quickly cause lasting damage. Of all the job descriptions I have read it appears this office is closer to a principal than a headmaster and creates a kind of first among equals
I have never been afraid of the word "elite" or even being called "elitist." Unfortunately, over time, the word has become more and more pejorative. Subsequently, since many view the term headmaster as "elitist" the title has been avoided except at schools stressing academic rigor. This has forced a search for a term with which "faux egalitarians" feel more comfortable.
The complications of schools with a head administrator are numerous. Actually when I think of this I am reminded of the "old saw" that a camel was actually to be a horse, but was designed and built by a committee. To be sure the head administrator concept is poorly advised. Time and space here do not allow for an exhaustive, or even detailed, analysis and exposition of all of them, so I will limit myself to four: boundaries, authority, philosophy, and fundraising. Consider this; I am not speaking off the top-of-my-head, but from experience. I have lived this.
For any institution to run smoothly boundaries need to be clearly defined. This aforementioned scenario by design is vague. The head administrator is neither a headmaster nor a principal, but created as a hybrid to cover both positions. The initial problem is the expectation; it is too great and forces poorly advised strategic decisions to be made.
Since a headmaster is required 60% time as a fundraiser, an advocate for the school, something many don't enjoy, this is usually the first thing to go leaving a tremendous void. Day-to-day expectations place a heavy demand on the job eating up inordinate amounts of time. Board, committee, and advocacy demands force delegation of these or more often simply allows over achievers, aggressive personnel, to step in and fill the vacuum, somewhere they don't belong. In my experience it is not uncommon for the director of development to take this unfortunate step, usually alienating and offending the education folks. The development job description is clear. Taking on these additional things activities cause administrative problems which go far beyond interpersonal ones.
With this fracturing of administration and personnel tension, authority becomes unclear. Who is in charge and in charge of what? Now, someone is probably doing or infringing on counseling without authority, or advising students about college or course load, advocating for one program over another, and in general causing an unraveling of institutional order.
Educational philosophy and implementation of policy, the headmaster's job, has become a community project. This causes a loss of edge, the watchful eye, and the continuity of the one designated to assure philosophical unity. In essence it is reminiscent of ancient Israel when "everyone did what was thought right in their own eye." Put another way a mess is created.
Since fundraising, the job of the head-of-school, is so consistently unpopular with even directors of development avoiding the heart of the job, operating "in the black" seems impossible. A ubiquitous characteristic of donors, particularly major donors, is that they like to hand their gift to "the decision maker." This means the board chair or the headmaster. Now, before there is confusion the designation of a major donor varies from school-to-school. My experience has revealed ranges from $500 to $50,000+. The head administrator doesn't qualify in a donor's mind and the director of development while perhaps the "cultivator" is viewed as a secondary level officer. Without the appropriate officer, a school is left with no one to take to the dance.
Someone has to be in charge and what you call that person will have a profound effect on your school. Titles must be easily recognized and clearly defined in the mind of the general population. Policy should divest itself of baggage when it comes to leadership titles, academic philosophy, and even dress code expectations. The more specific you can be, the easier your job will be, and greater the successes you achieve!
These successes cannot be accomplished alone, but thrive in community and cultivated through learning relationships with others who have struggled and known success. A wonderful Christian and one I would call a folk philosopher Charlie "Tremendous" Jones has provided pertinent advice: "If you hang around achievers, you will be a better achiever; hang around with thinkers and you will be a better thinker; hang around with givers and you will be a better giver; but hang around with a bunch of thumb sucking, complaining boneheads, you will be a better thumb sucking, complaining bone head!"