How to Write a Cover Letter

If you want to hear groans, ask a group of recent college graduates what they think about cover letters. You won’t be disappointed. Cover letters have become one of those generic formalities that are part of the job application process but are completely useless, like interview thank you notes. The cover letter sits there on your checklist until you force yourself to painfully write one.

This makes the majority of cover letters really bad. Generic writing isn’t interesting to read, but generic personal writing is even worse. Hiring leaders aren’t excited to read cover letters because they know what they’re getting is a long-form rendition of their applicant’s resume, bookended by a couple of statements customized for the role in question. Their lack of interest, in turn, reduces the overall importance of the cover letter, which drives us all to put less thought into writing them. It’s a self-sustaining loop.

I always felt similarly about cover letters. I had a shell of a letter that I thought worked well, and I would slot in a new company’s name, think hard for fifteen seconds about why I wanted to work for that company in particular, and add that nugget to the first and final paragraphs. The end product was generic – but I didn’t have the willpower to spend more time or the courage to break the mold.

About a year ago, I thought I might be moving to the Bay Area. I found a job that sounded great, at a consulting firm that supports charter schools, and I sent off my application. A week later I got a call from the hiring leader: “I have to tell you, both myself and the leadership team absolutely loved your cover letter. We don’t usually pay much attention to online applicants but we felt we had to talk to you.” I was floored – my cover letter had worked (PDF here and below).


Be Genuine

Step one in writing a cover letter is to take a giant step back and ask: What do I want to convey? In this case, I wanted the recruiter to know I had great interpersonal skills, am a quick learner and am passionate about education. Those key messages were tailored to the job – I would work with partner schools, have to learn about charter school funding and ideally care about the charter school movement – but they were not fabricated. That is key. The only way to convey your fit for a job is to actually think about why you’re a fit for the role. Don’t just say what they want to hear.


Use Concrete Examples

Most of us know that job descriptions are meaningless until you are a part of the company in question. They are vague. Do not regurgitate your job description into your cover letter. Start with the qualities you are looking to convey (interpersonal skills, quick-learner, education-focused) and identify times when you have demonstrated those qualities.

In my example, I highlight that my interpersonal skills have led to being “given two direct reports,” to being “an effective English teacher,” and to being “asked to join the school’s board.” In relation to learning on the job, I indicate I’ve come up to speed quickly in two industries, and in a job-function I didn’t study in college. I then finish with a list of education-related organizations I am a part of and my history volunteering in a similar capacity for most of my life.

If possible, include concrete examples of research you have done. “I met with Jane Doe and was impressed by the resources available for personal development,” etc…


Make It Personal

Cover letters are intimidating, primarily because of their formality. You are putting your voice on the page, and hoping that a job interview comes out of it. I can understand why we decide to play it safe. But I’ve read through fifty, sixty cover letters in one sitting. Formality is boring. My experience has shown me that it is the people who stand out whose cover letters I appreciate and read closely – and it doesn’t take much to stand out.

Here are some ways I incorporate personal flourishes into my letter:

  • “I am, first and foremost, a people person”
  • “I love the energy of school organizations”
  • “[I] am constantly organizing friendsgivings, wine and cheese mixers and any other excuse to bring friends together”
  • “[your community] feels like a place I will be happy to call home”

I know – we’re all told that there is no upside to being unique in a cover letter. But do you really believe that? There is tremendous upside to putting the real you on the page, and doing so doesn’t require exclamation marks and goofy cliches. If, for example, you want to show that you love technology, then show that you love technology! “Wired magazine has always been the first thing I read each morning.” Or: “I taught myself web design after falling in love with blogging in high school.” How much better do those sound than, “My technical competency in web design, developed over a five year career in the field, makes me a good fit for X company?” Ask yourself which version you’d like to read.


Get An Outside Perspective

Your cover letter will be read by someone who doesn’t know you or your experience. They also won’t want to read your cover letter (no one really does). So have a friend read through yours, and get their feedback. Did it hold their interest? Did they skip over entire sentences, or paragraphs? You aren’t an objective judge of how your own writing sounds, so have someone else take a look.


Have questions? Email me at [email protected] – I am one of the sick few who love reading cover letters!

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