Presenting Yourself on Paper
Tips for Crafting a Successful Cover Letter,
Résumé, and Statement of Educational Philosophy
Successful educational leaders are nearly always successful communicators as well. So it is entirely
appropriate that search committees carefully scrutinize the application materials of candidates for Head
of School and other senior administrative positions. In addition to information about the candidate’s
credentials and qualifications, the résumé, cover letter, and statement of educational philosophy 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. If you stumble here, you are
unlikely to advance to the next stage.
All written materials should be:
1.
Free of grammatical or typographical errors. While this seems like a stunningly obvious
bit of advice, many of the application packages we receive contain one or more of these blemishes.
The moral: Everyone needs a good proofreader!
2. Attractively and cleanly presented. You don’t have to be (or hire) a graphic designer, but you
should ensure that the documents you present are uncluttered, readable, and professional in
appearance. Avoid unusual typefaces, tiny font sizes, and decorative stationery designs – all of
which can make your materials difficult to read and reproduce.
3. Concise. Search committee members are busy people who do not want to wade through wordy
cover letters and résumés or pages and pages of marginally relevant supporting materials. You
want to keep them focused on your core achievements and most significant contributions.
Here are some specific tips to help you with the three major components of the application package: the
résumé, the cover letter, and the statement of educational philosophy. (This advice reflects the process we
use at Wickenden Associates; other search firms might have different views.)
Your Cover Letter
The cover letter represents your first chance to sell yourself to the search committee. It allows you to
elaborate upon the bare bones of your résumé, convey enthusiasm about the position, and make the case
for your suitability for the job. A good letter also gives the reader a strong sense of the candidate’s
personality and leaves the search committee eager to learn more about you.
Bear in mind that, in most cases, your application will be part of a large notebook of materials that the
search committee must digest. A well-crafted cover letter can go a long way toward setting you apart from
other candidates. Invest particular effort in the opening paragraph. Don’t, for example, begin with “My
name is. . .” – a surprisingly common and uninspired approach.
If you are using the exact same cover letter for more than one position, you are missing an opportunity. The
best cover letters are carefully tailored to the particular job. The letter should demonstrate that you have
read the Opportunity Statement and given careful thought to the ways in which your skills and experiences
match the school’s requirements and challenges. This is the place to inform the search committee about any
connections you might have to the school or to the community in which it is located. The letter should also
highlight the congruity between your sensibilities and the school’s core values.
1000 Herrontown Road, Princeton, New Jersey 08540-7716
Tel: 609-683-1355
Web: www.wickenden.com
Email: [email protected]
While composing your cover letter, try to anticipate and gracefully address any questions or concerns a
search committee is likely to ask while looking at your résumé. If you took a break from the professional
world, switched careers, or left a recent job sooner than expected, someone on the search committee will
wonder why. You do not want them guessing or, worse, believing that you have something to hide.
Some of the best cover letters offer career highlights while presenting a broader career arc or trajectory.
Take the opportunity to think about how you would like them to connect the dots. Consider the motivations
for your professional moves and the story you want to tell about yourself and your career.
The cover letter may be addressed either to the search committee or to the consultant(s). One to two full
pages is an appropriate length, although a somewhat longer one can be effective if it is well thought out
and packed with relevant information. A letter of only one or two paragraphs, on the other hand, is likely
to come across as perfunctory.
The Résumé
Your main goal in developing your résumé should be to highlight your qualifications and experience
without too much extraneous detail. For most people, a two-page résumé is more than adequate. The
trajectory of your career should be apparent – presented logically and chronologically.
1.
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 descriptor of the school (key
mission elements, enrollment size, grade configuration, city and state) or organization as well as
the scope of your responsibilities. If you have held multiple positions with one employer, indicate
titles and dates of those positions as sub-headings, including date ranges for each position held.
2. We do not recommend that you organize your résumé by responsibilities rather than positions.
For example, some candidates present their experience under separate Administrative, Teaching,
and Coaching categories – even though these positions were at the same school and often held
simultaneously. This structure can be confusing to the casual reader and makes it difficult for
search committees to assess the scope of your responsibilities within an organization.
3. Many leadership roles in schools are critically important to the institution but don’t rise to the
level of an official position. If you want to highlight your work as a committee chair or leader of a
task force, for example, provide brief contextual information that illuminates the breadth and
depth of the group’s impact on the school as well as your specific role.
4. Do not omit dates from your résumé in an attempt to obscure information you would rather not
convey (e.g., your age, 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.
5. Do not include a photograph.
6. Avoid including a cute or overly casual email address as part of your contact information; if
necessary, establish a new account with a more professional tone.
7.
Lengthy lists of publication, awards, or professional development activities are best presented as a
supporting document rather than as an integral part of the résumé.
Supporting Materials
To complete your application, we initially require a list of three professional references. (Submitting
more than three names at this stage is neither necessary nor desirable.) Your referees should be
individuals who work with you now or have done so in the recent past. Ideally, the list will include your
direct supervisor. We recognize, though, that this is not always possible if your search is confidential. Rest
assured that we will not contact any of these references without seeking your permission first.
1.
The reference list should be provided as a separate document, not included within the résumé.
2. Include phone numbers and email contact information for each of the references, as well as a
brief description of the context in which they can speak about you.
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We also welcome letters of recommendation from current or former professional colleagues, although
these are not a required component of our process.
If available, it’s a good idea to include with your application package supporting materials such as an
article you have written or a speech you have delivered that provides insight into your values, your
professional interests, and/or your communication skills. In total, these documents should not exceed
about 10 pages. Although you will be submitting your materials to us electronically, the search committee
will in all likelihood be reviewing them on paper. As a result, including extensive links to your blog, other
online publications, or videos is not a substitute for printed documents.
The Philosophy Statement
The Statement of Educational Philosophy serves two important purposes:
1.
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.
2. It provides a writing sample, helping the committee to see how well the applicant can
communicate about education to an audience that includes non-educators.
Although the focus of this document should be your educational philosophy, candidates often incorporate
information about their leadership beliefs and style as well. Please don’t approach the philosophy
statement as a piece of academic writing. Jargon should be avoided, and there is no need for elaborate
citations of sources or discussions of educational theory. Your goal should be to convey the values and
beliefs that underlie your professional practice. Anecdotes are perfectly fine, particularly if they help to
illuminate your approach to students and colleagues. One to two pages is an appropriate length.
Nuts and Bolts
As per the instructions on the last page of our Opportunity Statement, your application materials should
be submitted via email attachment to [email protected]. You may send your application
materials as separate files or a single document. We do appreciate it, however, if you send them in a single
email rather than multiple ones.
A few tips:

Use common file formats such as Microsoft Word or Adobe Acrobat (pdf files). Again, avoid
complicated formatting and unusual typefaces, which may not transmit well.

Do not include the cover letter in the body of your email. An attachment will look much more
professional when we present your credentials to the search committee.

Please don’t assign your files generic names like “résumé” or “cover letter,” as we are likely to
receive numerous files with that name – particularly on deadline days! “JSmithresume” is better.

After sending your application materials via email, please do not also send them via regular mail,
fax, or express services. Multiple copies of the same material merely generate confusion.

We acknowledge receipt of all applications promptly. If you have not heard from us within one or
two business days after submitting your application, please give us a call at 609 683 1355 to
confirm that we received it.
Finally, if you are new to the independent school search process (or even if you’re not) don’t hesitate to
ask questions or seek advice about the presentation of your application materials. While it is not
appropriate for us to provide substantive editing, we are quite willing to offer general guidance. Ensuring
that candidates present themselves fully and well serves the best interests of everyone involved in the
search process.
Founded in 1986, Wickenden Associates has conducted more than 400 Head of School and other senior administrative
searches for independent and charter schools located throughout the U.S. and abroad. For information about our search
and other consulting services, contact Wickenden Associates President Jim Wickenden ([email protected]) at
609 683 1355. This and other articles of interest to independent school Heads, trustees, and aspiring school leaders are
available in our online library (www.wickenden.com/leadership-library).
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