01/17/2013 by Carney Sandoe Staff |

5 Ways to Kill a Cover Letter

business woman's hands writing with pen

You’ve been job-searching for months when you see that perfect job listing (if you’re a candidate with us, it appears in the form of a referral in your inbox). You’re itching to send your materials and start the interview process. Resume, check. Personal statement, check. Letters of reference, check. The only thing left? The dreaded cover letter. After countless “To Whom It May Concerns,” over these past weeks, you’re suffering from cover letter burnout.

If you feel this way, watch out! Don’t skimp on the time it takes to craft a good cover letter. Avoid doing these five things — they can kill a cover letter and, with it, an otherwise excellent applicant file.

1.  Sending a Sloppy Cover Letter

What do you tell your students when they submit papers? Proof, proof, and then proof some more. Follow your own instructions when writing your cover letter. Resist the urge to rush through it — errors could make you appear frazzled, careless, or — worse — apathetic about the job opportunity. Check your work carefully for grammatical mistakes, and triple check your spelling — especially the names of the hiring contact and the school.

2.  Sending a Generic Cover Letter

“Dear contact. I’m interested in the position. I’m confident my skills meet your needs. My experience supports that hypothesis.” Write, rinse, repeat.

It can be tempting to copy and paste your cover letters, particularly if you’re applying for the same type of position (e.g., you’re applying to teach Spanish at four different independent schools). But when you mass-produce your cover letter, you lose the opportunity to show a hiring contact how your skills and experience meet that school’s specific needs. If your cover letter only briefly acknowledges the school to which you’re applying, the reader will be able to guess that you’ve copied and pasted — and she might doubt the depth of your interest in her school. Do your homework on the school, its values and its mission, and offer a few distinct points that show the hiring contact why the school needs you, not the other way around.

3.  Sending a Too-Specific Cover Letter

Be wary, though, of being overly-specific about a school. If you spend several precious paragraphs re-hashing information you read on the school’s website, you’re allotting yourself less time to present your case to the school. A hiring contact wants to know that you’ve done your research, not re-read her school’s existing materials.

Acknowledge the unique qualities of the school, but don’t forget to tie these qualities back to your own expertise. It’s not enough to delineate the reasons you find the school interesting or exciting — you need to show how you can help the school continue to progress and succeed.

4.  Being Too Long-Winded

We know — it can feel impossible to keep your accomplishments, interests, and innovations to roughly a page in length. As your career goes on, your list of achievements lengthens, and you want to share those achievements in your cover letter. Is brevity really all that important?

The short answer is yes. You don’t have to agonize about pushing a paragraph over a page, but don’t wax on much more than that. Remember that a hiring contact is reading dozens upon dozens of cover letters. Keep her interest, and keep it brief.

5.  Paraphrasing Your Resume

The cover letter is a rare opportunity for creativity in the job search. While you want to reinforce the points you’ve highlighted on your resume, don’t turn your letter into a summary of your C.V. Select a few important points from your career and bring them to life — that will speak volumes more than taking the reader on a chronological journey from student teacher to department head. The documents in your file should work in tandem; your cover letter should complement your resume, not rehash it.


Your cover letter is an opportunity to distinguish you from other candidates. Don’t let burnout hurt you! And if you’re a candidate with CS&A, don’t forget to let the hiring contact know.

Have any more tips for writing a cover letter that gets noticed? Weigh in below! And if you’d like more help in your teaching or administrative job search, let us help you—apply online today.

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1 Comment

know-net 7/31/2020 at 5:38pm

In addition, don’t be lazy about your cover letter. If the job posting doesn’t specify a person to address your cover letter to, do some research to see if you can find a specific person to address it to. You can try calling human resources if an Internet search doesn’t help you. If you can t get find the name of a specific person, you should at least address the letter to the specific department, or try: Dear Hiring Professionals or Dear Selection Committee if you really can’t find a specific name.