What Aspiring Heads Should Know about Headship

Wickenden Associates
September 5, 2019

Headship is not for the fainthearted. Headship is awash in ambiguity. It is long on accountability, short on autonomy. It is a balancing act extraordinaire—juggling the competing and conflicting demands of half a dozen constituencies, always with an eye on the “big picture.”

Success often depends on being temperamentally suited to “the crush, the rush, the relentless visibility” of Headship, and these sentiments have been echoed time and again by many of the Heads we’ve placed. We often hear that there are skills and qualities essential to success in one’s first Headship, and among those that top the list are:

  1. Strong communication skills, both oral and written
  2. The ability and willingness to listen
  3. Abundant emotional intelligence
  4. A visionary, strategic, “big-picture” orientation
  5. Equanimity—including patience, an even temper, a calm manner, resilience, and a thick skin

There are also areas in which new heads should be immediately prepared to engage: Head-Board relations, hiring and recruitment, public speaking, effective writing, fund-raising, long-range planning, faculty and staff evaluation, faculty and staff development, personnel supervision, community relations, time management, budget, and teaching. Although managing the Board is a daunting challenge—and often the source of their greatest missteps—we often hear from new Heads that they have forged stronger relationships with their Boards and Board Chairs than with students, parents, or faculty.

Heads must be life-long learners. Finding time for workshops and seminars to achieve expertise in specific areas, such as fund accounting, fund-raising, staff development and evaluation, long-range planning, time management, and school law is often a necessary aspect of the job.

Since nearly all Heads hold at least a master’s degree (several hold more than one), and some hold doctoral degrees, it will be necessary at some point in your career to earn an advanced degree. Our best advice for pursuing an advanced degree is not related to specialization—but rather timing. If you plan to pursue an advanced degree, do it before you accept your first headship, since the demands of school leadership do not leave time for graduate work.

Regarding the pipeline, we often hear that Boards are increasingly seeking “non-traditional” candidates, yet we find that is simply not the case. More often than not, Heads come from positions inside independent schools. So, for those aspiring to Headship, there really is no substitute for learning by doing. Many with whom we’ve spoken recommend that aspiring leaders experience any or all of the following:

  • Run a summer school or some other comparable major institutional program that involves many constituencies.
  • Have your Head help you work closely with trustees in areas of finance, buildings and grounds, and development.
  • Ask for opportunities to sit at Board meetings and subcommittee meetings, especially on strategic planning, finance, admissions, marketing, financial aid, etc.
  • Find a way to play a role in support of a Head at Board meetings, in personnel matters, and in fund-raising.

Critical to the success of this strategy, of course, is the existence of a supportive supervisor, not just an effective Head but a Head who shares and supports your aspirations. Largely unspoken but clearly implied in this is the notion that to be your best you must work for the best. For an aspiring Head, then, looking for a job really means shopping for a mentor. Judicious career choices become all-important.

In general, a new head should expect to be totally absorbed in the work—working long hours and long weeks for a long time. Essentially, this is a job in which you are never “off duty.” Yet, Heads cannot afford to lose sight of the world beyond the schoolhouse door. As a new Head, you will need to stay attuned to the needs of your own family; make time for the physical exercise that will give you the stamina you need; broaden yourself through travel, reading, and reflection; keep your avocations; and take vacations to refresh and restore your vision.

The job is difficult, to be sure, but certainly not impossible for leaders who are also learners. The message to aspiring independent school leaders is clear: Prepare to be surprised and to surprise yourself.

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