Doing that song and dance: How to write a compelling cover letter

I am not a human resources professional. Hiring people is not my job. Except when it is.

In the last three years I’ve read 250-300 job applications, for a mix of part-time, student, staff, and librarian positions. I’m rarely the one to make a final hiring decision, but frequently I take the first pass through the applicant pool, identifying the candidates we will interview, and eliminating those we won’t. I’ve also sat on search committees and helped colleagues triage applications for positions they have posted.

In short, I have read a lot of cover letters, and can tell you exactly what does and doesn’t boost your chances of getting an interview (in my small corner of the universe). But before I do that, a couple of caveats:

Boring disclaimers

  • I’m not going to give you checklist. I can smell a cover letter based on an template from 100 yards away. I don’t hold it against people that they’re researching how to write a good letter, but I often find that these formula letters just don’t tell me what I need to know.
  • My advice will not apply to every situation. I work in a university library. The positions I’m filling usually require some technical competence, but our goal is to find a smart, hard-working, good-fit person who can learn the tools we use. We’re a service-oriented, non-profit, academic organization. My comments necessarily reflect this environment and this bias.
  • I am going to call upon the great movie musicals of our time to help me convey these thoughts
  • My opinions are my own, and do not reflect those of my employer.

OK. That’s done. Let’s get down to business (to defeat the Huns). Wait. Did someone say something about musicals?

But it’s just an empty stage!

This is your job when writing a cover letter:

No, not to use your tan arms and tapping feet to seduce the down-to-earth ingénue reading your application. (Unless you think that will work. Ha! Ha!)

The purpose of your cover letter is to set the stage, to paint a picture of what it would look like if you were a part of this organization. Your resume is the empty stage: fans, lights, sets. All the stuff that equips you to do the job. But the letter is where you give me the sunset, the mist, and 500,000 kilowatts of stardust.

The cover letter is your chance to help me see what you see when you imagine having this job. In order to do that, of course, you have to actually know what it is you see when you imagine having this job.

And how the f*** are you supposed to do this?

You gotta know the territory

Read about the organization. What is their mission, what are their values? If there are any controversies or news in the field, where does this organization stand? Are there words that come up over and over again on their website? Concepts or philosophies that they clearly espouse? Incorporate these into your letter.

Try not to be obvious about it, especially if what you learn isn’t directly relevant to the job opening. “I first learned about your company due to your high profile lawsuit, and I hope to hear the verdict from within your confines” may not be the way to go (or maybe it is…!). You don’t need to describe how you went looking for the mission statement on their website. You don’t even necessarily need to say, “As written in your mission statement….” They know what their mission is (well, hopefully). And if your words are consistent with it, your letter will resonate.

The point here is to pick up on what the organization cares about, and demonstrate that you also care about (or at least have a grasp on) those things. This will help give the impression that:

By George, she’s got it!

The feeling I want to have when reading your letter is: this person just gets it. “Getting it” has to do in part with understanding the organization, as above. Hopefully your background research will help you out here.

It also has to do with understanding the posting. This can be harder. Sometimes postings are poorly written (guilty!). Maybe you found it on a third-party site and have no way to ask questions or get more information. You kind of have to do the best you can with what’s written. So read it, carefully. Lots of times.

Finally, you can show you “get it” by focusing on the problem at hand (the job we need you to do) and on the future where you help solve it. Illustrative examples from your past are all well and good, but if the main message of your letter is “I have done lots of things well,” that doesn’t help either of us. 80% of the applicants have done lots of things well, but only like 3% of them leave me thinking, “By George, she’s got it!”

Show me now!

Words, words, I’m so sick of words….

When you’re telling me about yourself, please do not copy and paste any language either from your resume or from the job posting. OK, so you’ve been told to address the job requirements in your cover letter. But writing “I’m detail-oriented, hard working, and can balance many tasks at one time,” is not useful. Well, it shows me you read the posting, and I can appreciate that. But simple confirmation is not enough. Most applicants can say the same, and do, and are, and will.

Instead, think seriously about what you want the reader to remember about you when they finish the letter. Pick one thing: that you are a strong leader, flexible in the face of adversity, a quick learner, a creative problem solver, have a diverse range of experience, whatever. That doesn’t mean that you have only that thing to offer, or that you can give me only one example. It means your cover letter has one coherent message. Then, convey this message to me with different, concrete examples and illustrations from your experience.

And, finally:

You must stop these doubts, all these worries

Trust yourself more than you trust a template you found online. In the letter, yes, I want to see that you are professional and competent. But I also want to see you. If you use short, clipped language, do that. If, like me, you are verbose and prone to many subordinate clauses, do that. If you like bullet points better than paragraphs, do that–as long as your bullet points are thoughtfully crafted and don’t duplicate your resume or the post requirements.

Don’t feel like you have to abide by arbitrary rules that some website told you are important:

  • I will not throw your letter out if it’s two pages long.
  • I will not throw your letter out if you address it to the wrong person (but seriously, if you don’t know for sure–and sometimes you can’t know–just use To Whom it May Concern).
  • I will not throw your letter out if you abstain from telling me you saw the posting on a friend’s Facebook wall.

I will throw your letter out if it does nothing but repeat information available elsewhere, if it is irrelevant, or (most importantly) if it doesn’t tell me enough about you to differentiate you from the other candidates.

I don’t mean that every letter needs to be an exercise in creative writing. I count on there being some similarity across letters. You’re all trying to communicate the same thing through the same medium. Of course there will be overlap. Don’t be weird just for the sake of being memorable. But within the bounds of reasonable professional correspondence, I want to hear your voice.

I hope this might be useful to you–as a thought exercise if nothing else–as you search for jobs. Good luck, all!

P.S. Just one more thing, a pet peeve really:

One singular sensation

Try to resist the temptation to declare that you are “perfect” or “ideal” for this position. Keep in mind that some poor sap (me) is reading like 70 of these things over the course of a couple of hours. There’s no such thing as a perfect fit, and around the 20th person to declare that they are it, I’m feeling ready to make a drinking game out of this.


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