No Party Here
I can't tell you how many cover letters I've written in my life. Probably enough to get an entire town's worth of people a job or a fellowship or a grant. It's not exactly against the Geneva Convention to write your own cover letter: it's not torture so much as torturous. Nevertheless, it ain't fun.
And it requires you to be a psychic. You have to -- or at least you feel as if you have to -- know exactly what your audience wants to hear from you and what tone they want to imagine you're saying it in. Should you be specific? (Answer: yes, but don't repeat details that are already in your resume. Be specific about things that are between the lines of the resume.) Is your tone too haughty or braggy? (Answer: if you're a shy or unsure person, probably not, but if you're an ostentatious or aggressive person, probably.) Should you stay conventional, or can you use bold, bullet points, or italics to highlight portions of the letter? (Answer: depends on your industry, the organization you're applying to, and how you want to portray yourself.)
And you could ask yourself questions like that over and over, pouring over each word as you go. It can quickly become an exercise in masochism.
How I Learned to Stop Worrying and Love the Letter
Writing cover letters for other folks -- especially when I've already written their resumes -- doesn't produce nearly the same amount of sweat for me as writing my own cover letters. It's easy for me to compare their resumes to the descriptions of the jobs they're targeting (or ones similar to jobs they'd like to have) and find the stand-out connections between the two. The cover letter then becomes a narrative of those connections. I often have to ask for some elaboration on the resume so that I can avoid repeating the facts of the resume within the narrative of the letter. For example, when I applied for assistant professorships around the U.S., I described my actual teaching practices using an example or two of the exercises I'd used in my composition classes. I was specific and succinct about what happened in class and what the outcomes were, details that didn't belong on my CV but that revealed the significance of my list of "Courses Taught" there. Those are the kinds of details that stand out in cover letters.
Recommendation letters can be a special source of concern for anyone who does any mentoring. Just like with cover letters, you want to make sure that you're highlighting the most important achievements to make the best opportunities possible. When I was the administrative intern and teaching mentor for the first-year writing program at the University of Kansas (lo these many years ago), I found myself writing dozens of recommendation letters for my undergraduate and graduate students. It was a labor of love, and it gave me a sense of my own accomplishment to see how much my students had accomplished and what those accomplishments set them up to achieve in the future.
Then I had to start applying for my own jobs. And writing my own cover letters. Which were awful. I'm sure that my dissertation director would say to this day that my first cover letter drafts were abominable, probably my worst writing ever. They were too long, too specific, too emotive, too formulaic, and too long (they were really long).
Then one day, it hit me: I'm struggling to write because I think this letter is supposed to be the something like my professional manifesto. It's not. A cover letter isn't supposed to be my defense before the Inquisition. It's a document that's supposed to clarify how Item A (my CV and professional history) aligns with Item B (the job description and institution that I'm applying to) in ways that could create Outcome A (the ideal situation in which I get the job, flourish in it, and my accomplishments become not just value-added but integral to the institution). Because I put so much pressure on myself to get the letter "right," I struggled to write effectively.
So, as a rhetorician, I came up with a new strategy: I would write my cover letter as if I were writing a recommendation letter for someone else.
The Recommendation Strategy
I sat down to write a draft of my job cover letter as if I were writing a recommendation to the same job for one of my favorite mentees, Rachel, one of the kindest, most assertive, insightful young scholars I know. She was the ideal subject because we were on much the same professional path, so as I explained how the items on my CV fit the job description, it wasn't hard for me to substitute "I" and "me" and "my" for "Rachel," and "she" and "her."
Yes, this required some careful proofreading later, but it saved me hours of time and mountains of grief because it helped my letter-writing flow. Instead of worrying about bragging too much or being too humble, I was able to write with confidence because I genuinely want good things for Rachel. I want them for myself, too, but I found it more natural to sing Rachel's praises than to toot my own horn. Granted, I wasn't actually doing that -- promoting Rachel -- but it helped me feel less timid and unsure about asserting that certain concrete experiences match up well with the demands of the job.
So, my advice for writing cover letters is this: if you're struggling to get a draft down, don't write your letter for yourself. Write it for someone else. Pick someone you admire, like a colleague, a mentor, a mentee, a family member, or even a fictional character. Use your resume and the details of your own experiences (of course, don't use their accomplishments instead of your own, and never ever embellish your experiences!) but write as if you're recommending the person you admire or want to see succeed instead of describing yourself. Then go back and put your name in where the other person's name appears. Finally, check it over: Is the letter accurate regarding your experiences and qualifications? Does it sound appropriately commendatory? Would you be willing to send it on that other person's behalf? If so, you've probably got a great cover letter for yourself, and you've avoided testing the limits of the Geneva Convention!
Of course, there's another way to avoid the masochism of writing a cover letter: ask me to do it for you :)
If you've got other strategies for writing cover letters, feel free to mention them in the comments below!