Presenting Yourself on Paper: Tips for Your Application Package

Jim Wickenden, Founder, Wickenden Associates
September 12, 2019

Successful educational leaders are nearly always successful communicators as well, so it is entirely appropriate that search committees scrutinize the application materials of candidates. In addition to information about the candidate’s credentials and qualifications, the résumé, cover letter, and statement of educational philosophy (for head of school candidates) also provide important clues about an applicant’s writing skills as well as their approach to their audience.

The application package is the first hurdle in the multi‐step search process. At this stage, the search committee is charged with whittling a large field of candidates down to a more manageable size. Stated another way, some on the search committee may be looking for reasons to eliminate you. If you stumble here, you are unlikely to advance to the next stage. Thus, your application materials should be:

  • Free of grammatical or typographic errors. While this may seem obvious, many of the submissions we receive contain these blemishes. Everyone needs a careful proofreader!
  • Attractively and cleanly presented. You don’t have to be a graphic designer (or hire one), but you should ensure that your materials are uncluttered and professional. Avoid unusual typefaces and overly decorative backgrounds.
  • Concise. Search committee members are busy people. They do not want to wade through wordy résumés or pages and pages of marginally relevant supporting materials.


Your main goal in developing your résumé should be to highlight your qualifications and experience without extraneous detail. For most people, a two‐page résumé is fine. List your professional experiences in reverse chronological order, with the most recent job first. Include the years spent in each position, titles held, and a brief description of the organization (including city and state) as well as the scope of your responsibilities. Do not omit dates from your résumé in an attempt to obscure information you would rather not convey (e.g., positions held only briefly or a gap in your work history). Gaps that are long enough to require an explanation should be explained briefly, either in the résumé itself or in your cover letter. Include, as a separate document, a list of three professional references, with an explanation of their relationship to you. Include phone numbers and email addresses


The cover letter represents your first chance to sell yourself to the search committee. Do not include the cover letter in the body of your email. Rather, submit your cover letter as a separate attachment. Cover letters should be long enough to demonstrate that you have carefully thought about the opportunity, but not so long that you lose the audience. More than three pages is too much. A compelling cover letter gives the reader a sense of the candidate’s personality and leaves the search committee eager to meet you. It’s best to avoid excessive use of the word “I.”

Candidates use the cover letter to demonstrate that they have read the position description and given some thought to the challenges facing the school. Surprisingly, not all candidates pay attention to the desired qualities and skills enumerated in the Opportunity Statement. If you can point specifically to the ways in which your experiences and skill set match the list of ideal qualities, you will increase your chances of advancing in the process. Above all, the letter should demonstrate enthusiasm and specify why you are intrigued by this particular opportunity. Well‐written cover letters are carefully tailored to a particular job. Remember that your materials are going to be reviewed by search committee members who love their school!


The Statement of Educational Philosophy, typically required for head of school candidates, serves two important purposes. First, it enables the search committee to evaluate the extent to which the candidate’s beliefs about education match the mission and philosophy of the school. Second, it provides a writing sample, helping the committee to see how well the applicant can communicate. Avoid jargon, extensive citations, or discussions of educational theory. Aim to convey the values and beliefs that underlie your professional practice. Anecdotes are perfectly appropriate, particularly if they help to illuminate your approach to students and colleagues. Try to convey your statement of educational philosophy in one or two pages.

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