5 Questions to Ask When Hiring a Headmaster

Right now, most schools are drawing to a close and headmaster needs for next year are known. Students can think of nothing but summer break (bursting through the front doors singing, “Schooooool’s out for summer!”), and the teachers feel roughly the same, but more so. For school boards and other governing bodies, however, the work is just beginning. Those searching for headmasters will sort through resumes and CVs, host personal and Skype interviews, hold marathon meetings, and do their best to wisely fill the vacancies of their school. In other words, the search is on!

So, for those involved in hiring a headmaster (an unenviable and difficult task), here are some questions you may find helpful.

1) What is a headmaster?

Some schools want headmasters; others want administrators. And while being a headmaster certainly involves administrative tasks, a true headmaster is far more. The term “headmaster” means “head teacher,” meaning he must be a teacher among teachers, able to train, inspire, and aid the growth of his teachers. He must be a lifelong learner in a community of lifelong learners. And, he must be given the necessary support and time to do so.

Consider this: Plato was a headmaster. Now, compare your expectations of a potential headmaster with that statement.

2) Have we clearly communicated our expectations of the headmaster?

In any relationship, communication must remain open, consistent, and honest. Nothing will sabotage the effectiveness of a headmaster like unspoken or unwritten expectations.

  • Have you clearly communicated the role and responsibilities of the headmaster?
  • What about the role of the board (or governing body)?
  • Is there clarity on which issues and areas fall under the headmaster’s authority, and which fall under the authority of the board?
  • Has there been confusion about these realms of authority in the past? What has been done, or will be done, to avoid it in the future?

3) Have we honestly divulged the needs, strengths, and weaknesses of our school?

Hiring a headmaster is not the same as courting a prospective family and, while attempting to boost enrollment should still be done honestly, it is understandable to put your best foot forward. A headmaster, however, must have the full story – warts and all. It may not be pleasant, but if a candidate is frightened away because the school is imperfect, then the school has dodged a bullet. Be honest. Do not violate confidences, or assassinate reputations. But, be honest.

4) Do the candidate’s strengths and weaknesses complement the needs of the school?

What are your school’s major needs? What role would the headmaster play in meeting those needs? Do the candidate’s strengths promise to meet those needs? If not, what would the board do to ensure they are met?

Do not hire a headmaster with the expectation that he will meet every major need. He is one man. If a candidate exhibits particular weaknesses, those must be weighed in comparison to needs and the board’s expectations must be adjusted to consider both his strengths and weaknesses.

5) How are we going to support his learning and growth?

With the candidate’s strengths and weaknesses in mind, the board must consider the means of support they will provide for the headmaster. Particularly, when the candidate is inexperienced as a headmaster, what will the board do to provide for his continuing training and education? Money for conferences, apprenticeships, consulting?

Additionally, what will the board provide to aid the headmaster in training teachers? Will his responsibilities involve providing in-house teacher training? Will the budget be constructed to include conferences for the headmaster and teachers? If the board does not provide financial and time resources for training, will they adjust their expectations of the headmaster and teachers?

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