How to Tackle the Cover Letter like a Rockstar

In keeping with the posts I've done in recent weeks on polishing your résumé and writing a snappy bio, I've decided to help job-seekers out there with my take on cover letters and how to best conquer them. In my career I've been on both sides of the hiring table, so I've seen a lot of what people struggle with and what makes for a great cover letter. I've also, of course, written a fair amount of them myself. And I'll tell you: It gets easier over time, but no one ever exactly looks forward to writing one of these.

But with these tips, hopefully you'll be a little less stressed about it. After all, you're a shoo-in for that job you're going after.

What is a cover letter do, anyway? I always think of the cover letter as the bridge that connects your professional experience with the relevant tasks mentioned in the job listing. Your résumé is just another slip of paper a tree gave its life for unless you explain why it's worth reading in full and how the skills you've amassed transfer over into what this employer is looking for help on. If there isn't a 1:1 ratio on equivalent tasks -- which there certainly won't always be -- talk about things you've done that are as similar as possible. Remember that you shouldn't decide whether or not to be applying for a job solely because you think you aren't qualified. I know so many people who talk themselves out of even trying for a job that they probably could've been considered for because they think they're not a good fit. Let the hiring party decide that. Plus if you aren't a good fit, maybe there's another job they have in mind and haven't even listed you'd be perfect for. You won't know if you don't send it off.

Length? Keep it short and to the point. Mine tend to be three paragraphs, at most, and always have an additional paragraph thanking them for their time and reminding them of where to find my contact information: at the top of the cover letter and also at the top of my résumé.

Font. Use Times New Roman. You can't assume anyone has any fonts beyond that, and it'd be a shame to not have your whole package read just because you used a goofy, hard-to-read or obscure font.

Don't massage the margins. That, along with using Courier New to pad out the length of a paper, are the oldest trick in the book. They're instantly recognizable and lame maneuvers. If your cover letter is actually so long it spills out onto a second page, you should start cutting words, not futzing about with the margins.

Don't use the template in Microsoft Word. I know, it's all ready and set for you to use, but guess what: Employers have seen it zillions of times. It reads as your just being lazy and having nothing to offer that stands out from the pack. There's really no need for fancy formatting or anything like that. Just put your contact information up top, and then jump into making your case.

What to include? Nobody wants to read about your paper route and how you once assisted your dad at his job at the ice-cream factory. Keep your sales pitch on yourself to what's relevant and trim everything else. The same holds true of your résumé.

Will they read it? Some of my friends use read receipts on their application emails but I would strongly advise against that. It's annoying to get a pop-up message in your email, and if you don't trust your potential new bosses to even open an email from you, then what does that say about your nature overall? Really, every tiny step you take with a new employer can scream volumes about you as a worker. So, chillax. Have some trust. And if you aren't picked for the job, remember: There's something better in store for you. Just be patient. Life has a funny way of working itself out, so don't fight it. 

David Wolinsky is a freelance writer and a lifelong Chicagoan. In addition to currently serving as an interviewer-writer for Adult Swim, he's also a columnist for EGM. He was the Chicago city editor for The Onion A.V. Club where he provided in-depth daily coverage of this city's bustling arts/entertainment scene for half a decade. When not playing video games for work he's thinking of dashing out to Chicago Diner, Pizano's, or Yummy Yummy. His first career aspirations were to be a game-show host.

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