I’ve been privy to a few conversations lately as to whether cover letters are still an important or relevant part of the application process. From my perspective, and certainly for school leadership positions, the answer is a resounding YES.
Why would you want to write a cover letter?
An opportunity to show your personality, sense of humor, warmth, and professionalism.
A cover letter provides a unique opportunity to share some facts, yes, but more importantly to reveal a little of your style. While you are talking about what’s drawn you to the school and why you are ready and interested in the position, a cover letter also allows you to give insight into how you might communicate with families, students, and the community. Written memos are a consistent component of school leadership, and your cover letter grants an opportunity for the decision-makers to get a sense of how you might come across to stakeholders.
An opportunity to show what’s important to you.
For those of us drawn to work with and support young people, we are often driven by some shared core values that put and keep us on the path of working in education. The cover letter is an opportunity to share your raison d’etre— your personal and professional mission for doing so.
An opportunity to honor an organization and show that you understand them.
Schools are inspiring places, and the people who will be reading your cover letter (board members, Head of School, leadership team, etc.) have chosen to devote a significant portion of their time and energy to that school. A cover letter provides the opportunity for you to highlight and recognize why folks would commit so much to that institution.
An opportunity to highlight a few of your key strengths.
You undoubtedly have a myriad of strengths, characteristics, and accomplishments if you’re applying for this leadership position—and it’s likely that your resume tries to speak to them all. In the cover letter, you have the ability to highlight the few that make the most sense for this particular position, as well as how these strengths show up in your work. This will help the committee see and understand how your strengths make you the right fit for the role.
Too often, I’ve seen candidates write cover letters just to check a box: the application asked for one, so you wrote one. Maybe you changed a few words from the last one you submitted, or merely changed the name of the institution and the title of the position, and pressed send. If this is your attitude towards your cover letter, you are better off submitting your application without one—not only does this practice make it unlikely that you’ll meet the four goals above, but it also likely undermines your candidacy. Lastly, it increases the dreaded likelihood that your cover letter will be one I open to find the wrong school or position name in the opening paragraph.
I’ve also talked to many candidates who want to submit their best application but don’t have a clear enough sense of what belongs in that letter.
A cover letter should focus on answering several “Why?” questions, including these:
Why this organization?
As mentioned above, the audience for your letter is people who passionately care about and deeply know the school. A key goal for your cover letter is to make sure the reader knows exactly why their school interests you: you should reference what excites you, what inspires you, and what has you curious about the school within your letter. While you might be applying broadly, the reviewer still wants to know that you did your research and found key points for alignment.
Why this position?
Maybe you want to move from an Assistant Head of School to a Head of School or from a dean position to an Upper School Director. No matter the role, your letter needs to specify why the responsibilities of the position attract you. All jobs contain aspects that you will find fascinating and aspects that you may find droll, or even pieces you dread (hopefully not too many or it may not be the right match for you!) Your letter should address a few of the tasks listed that you are particularly excited about completing in this role.
Why now?
This question is always on the mind of the letter reader. Your letter needs to address why now is a good moment for you to move to this position. Certainly, if you are looking after only a year at your current role or you’re finally looking after twenty years in the same role, you need to address this with more context and content, but the reason for your search should always be addressed, no matter the timeline. School communities often want to believe that the next person they hire for the role is going to be content in the position and remain at their school for a long time. If you are applying for this position, you are likely planning to leave your current role (and, in many cases, your current school)—so communicating why this opportunity is different is a key part of your narrative.
Why you?
A search committee will likely review many applicants from a variety of backgrounds. As with any job search, can almost guarantee that there will be people that appear to have more or better experience than you on paper, or that bring stronger preparation or a closer alignment than you for a given role. Your job in this letter is to help the reviewers see you in this role. You want to connect the dots for them as to why you, specifically, are a compelling match for this role, at this school, at this point in time.
A Bonus Tip
Hopefully you get it at this point: a personalized cover letter for a school leadership role is a worthy time investment. The last key tip is length. While the above information seems like a lot to include and you could likely fill pages trying to do so in depth, a cover letter should not be much longer than a page and a half. Answer the four whys, but with brevity and concision. In-depth exploration of your whys can wait until an interview happens, which hopefully your masterfully crafted cover letter will help land you!
