The Puzzle: Blog

The cover letter often takes a back seat to its more popular counterpart, the resume. Whereas the resume is poured over for hours, painstakingly formatted, and meticulously edited, the cover letter often doesn't get the same attention. For the most part, job seekers hate writing them and they are arguably the most dreaded step in the job application process.

But why? They are relatively short documents with fairly clear expectations. The cover letter's importance is widely debated, but when it comes to working with CS&A, it is unquestionably an important document. Many of our client schools ask for cover letters to indicate a candidate's interest in a position and to start the job application and interview process. Cover letters, therefore, should warrant the same care and attention that their partner the resume receives. They are, after all, one of the first introductions a school has of you.

While there are a number of cover letter mistakes that can banish an otherwise acceptable file to the “do not call” pile, the biggest cover letter mistake is also an easy one to fix — provided you’re willing to dedicate a bit more time to each cover letter during your job search.

So, what is the biggest cover letter mistake you can make? Spelling errors? Sounding too formal? Not being formal enough? The wrong length? Telling the wrong story about your career and work history? Selling yourself too much or not strongly enough?

The #1 mistake you can make when it comes to cover letter writing is: using the same or similar template for every position.

This shouldn't come as a total surprise. It can be tempting to create a standard cover letter, which you send immediately upon receiving a referral to any new position. That cover letter might address the most salient points of your resume, reveal your passion for kids and for your subject area, and address why you’re searching in the first place. You may even have this cover letter saved to your account on big-name job boards like Indeed and Monster and use it when you're quickly applying to jobs there.

But a template cover letter cannot answer the question each school asks when it lists a position: how can this candidate add value to our community? If you shoot out a generic letter, you’re not giving yourself the opportunity to answer that question and convince a school that you are the right person for what they need.

If you’re applying to dozens of positions, this might make you a little anxious — it can take a long time to craft a good cover letter. But you don’t have to start completely from scratch — you can keep many of the same information and sentences that you wrote in your generic letter. Just make sure to leave plenty of space in the beginning of the letter to explain which of your skills match with this school’s specific needs and mission at this time, and devote your middle paragraph — the “meat” of your cover letter sandwich — to highlighting experience that is relevant to this particular position.

For example, if you can teach chemistry and physics, and your “template” letter addresses your facility with each subject equally, that letter will not be as strong as a letter that gets into the nitty-gritty of your physics teaching experience when you’re applying for a physics-only position. If you’re an art teacher who prides yourself on your versatility, but a specific position description emphasizes the need for someone who can teach digital photography, then you’re missing an opportunity if you don’t spend several sentences demonstrating your mastery of that medium.

If you receive five referrals in one afternoon and are tempted to send out a generic cover letter to each ASAP — don’t. Take a bit more time to research the schools, research the position, and pinpoint the exact talents you have that would make a school hiring contact take a closer look at you. The extra time you spend now will pay dividends later on in the process.

Finally, one of the many benefits of working with CS&A as a job seeker is having your Placement Team as a sounding board and resource for all things job search. If you just received your first or second referral and you're really stuck on what to include in your cover letter, get on the phone with a member of your Team to talk through your concerns and get a trusted opinion from the experts at CS&A (we look at TONS of cover letters and resumes).

Looking for more cover letter resources? Check out our blog.

Are you also looking for your next teaching or administrative position at an amazing school where you'll thrive? Learn more and apply today to work with us as a job seeker. Our personalized job placement services are entirely free.

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2 Comments

careersboosters 5/9/2019 at 12:27pm

I have a little bit of experience so I’m not writing the cover letter with absolutely no work experience, so this will be very helpful for me to not to do mistakes before writing it. Your article is helpful and seems to work for me!

Stevie Ray Dallimore 2/26/2023 at 8:17am

New to CS&A, and looking forward to working with you all.