In my role as a search consultant leading and observing head of school search committees, I am conscious, now more than ever, of the importance of the cover letter in a candidate’s application. In fact, I consider it the single most important component of an application. I have met excellent candidates who never made it to the interview because they were eliminated from consideration based on their written materials.

While there are as many styles in which to write an outstanding cover letter as there are candidates, the cover letters that attract the attention of search committees have four characteristics in common. They are: 

1. The cover letter is, on average, approximately one and a half pages. There are exceptions to this rule, but I would encourage candidates who are tempted to introduce themselves beyond one and a half pages to do so with purpose. I would even go so far as to warn candidates who are tempted to go beyond two pages to do so at their peril. This reflection may be obvious and well known to candidates, but I would be remiss not to mention it. 

2. The cover letter must be personal and begin with a brief reference to what it is about a school and/or an opportunity that speaks to the candidate. It can be a mission, a motto, a strategic plan, or perhaps an impressive alumnus/alumnae with whom the candidate has crossed paths. This reference demonstrates that the candidate is serious about the school and has done their homework. More importantly, I believe such a reference acknowledges that members of search committees are selected to serve, in part, because they love their school. Why not indicate to these members what it is that you, too, might love about their school one day? This approach can serve to frame for candidates the rest of their cover letter. They can lean on several transitional sentences that express their interest and desire to join, contribute, and, where appropriate, to lead a community in which they find themselves in alignment. 

3. The cover letter includes candidates’ various roles, values, experiences, and achievements, and directly addresses a school’s particular challenges and opportunities. So strongly do I feel about this that I suggest that candidates take the time to put a list of a school’s challenges and opportunities on the right-hand side of their desk when writing their cover letter. It should be possible for a search committee to draw a dotted line from candidates’ roles, values, experiences, and achievements to their own school’s most significant needs at a given point in time. Candidates must explain why they are not only qualified to serve as head of school but might well be ideally suited to serve at the school to which they are applying. 

4. The cover letter must include efforts on the part of the candidate to anticipate and address head-on what it is about their candidacy that might make a search committee nervous. I call this self-scouting. Most committee members are new to reviewing applications for the head of school position and are prone to making mistakes or to drawing faulty assumptions. These are often the basis on which they decide not to interview candidates thereby depriving candidates of the opportunity to respond or defend themselves. It is important for a candidate to be honest about their candidacy. 

I hope in emphasizing the importance of the cover letter, I have helped future candidates persuade search committees to interview them. After all, only those candidates who are invited to interview with committees have a fighting chance to be appointed to be the next head of school.