How to handle the dreaded cover letter

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Let's be honest, cover letters are horrible. They're right up there (or more aptly, down there) with Mondays, visiting the dentist and breaking up via text (OK, maybe not quite that bad, but you get the idea). And then there's that whole confusion over email versus cover letter (does one replace the other, how formal should you be, do people even read these things?!). To clear up some of the confusion, we talked with Latin School of Chicago Senior Network Administrator Kevin Harig.

The first question we had was whether or not tech professionals should still bother with the cover letter. But the answer isn't so simple, because it all depends on the organization you're applying with. Kevin pointed out that plenty of people, especially in an educational institution like his, will still expect those items and will value them greatly. Still, when hiring people on the tech side, “nothing gets my attention like good credentials; work experience, certifications, specific listed, etc.” he said.

So, if you're on the fence about whether or not to write one, you should probably just write one. That said, here's the good news: Email will suffice. As a general rule of thumb, if you're submitting your resume directly via email to an actual human person, forget attaching a cover letter. However, if you do not have a direct contact and you're at the hands of machines, abide by the instructions listed.

Whew, now that we've got that all covered, let's go through some of the things you should and shouldn't do when writing the dreaded thing.


Clean it up

Your cover letter is meant to sell you, not to tell your entire professional story. Its sole purpose is to convince the hiring manager that you deserve an interview. Think of each sentence like a Tweet; you're working with as few characters as possible, so get straight to the point. Carry that brevity mentality over to your resume, too. As Kevin put it, “If an objective statement is long, I don't even give it too much merit.” That said, you should still be able to craft a well-structured sentence, “I want people that can write, don't get me wrong, but I am not hiring storytellers.”


Highlight your assets

Obvious, sure. But you need to flaunt those skills sooner than you think, and you  need to remember the aforementioned rule of not burying them in a bunch of fluff that nobody will ever care about except maybe your mother or your spouse. “Anyone can provide a nicely prepared statement, but that is not a skill I need them to have and it's not a reflection on the skills that I do need them to have. Give me the facts and figures, and let's talk.” Kevin also noted that after quickly drawing attention to those “brass tacks” items, you should express interest in continuing the conversation.


Stop describing yourself as an expert

When we asked Kevin if there's anything that should be omitted from the cover letter, his response was a simple one, “Never tell me you are an expert or that you know everything about a given topic.” He said that it's often an indicator of someone who's not as willing to learn. “I don't like the term, I also don't like anyone implying that they already know everything they need to know to do a job.” He said that a better way to show that you're a good fit is to simply state it. “Explain that you have extensive experience and knowledge that will aide you in performing a job, but that you are always eager to learn new things, something that is key to all tech positions.”

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Stacy Warden

Stacy Warden is a contributing editor of the Pluralsight blog and has worked in publishing since the dawn of the iPhone. Currently, Stacy deals in tech and education--a combination that she finds absolutely fascinating. You can find her on Twitter @sterrsi.