Easy, Breezy…Cover Letters?

Dear Amy,

First of all I wanted to thank you for your past advice for job searchers. Thanks to you I know to Always. Wear. A Suit. On interviews. Unfortunately, I need some help just getting to the interview stage so I can bust out my new, charcoal grey beauty.

So you have probably gathered, I am one of the billion or so Americans currently looking for a job. I have sent out hundreds of resumes and cover letters with no luck, and am beginning to wonder if I need a new approach.

I’ve always believed that cover letters should sound completely professional. They should focus on your work experience and skills. But many of the job postings I’m replying to say that one of the requirements for an employee is a sense of humor (usually it’s listed as a bullet point, right after “proficient in Excel and Word”). Up until now, when addressing their requirements in my cover letter, I’ve been ignoring the sense of humor. I mean, how DOES one convey this? A knock-knock joke? A sentence that reads, “I can assure you, I do enjoy a naughty limerick.” I have no idea. So I ignore it, figuring that my love of LOLs will be evident during the interview process.

But. Sigh. There ARE no interviews. Do you think I’m shooting myself in the foot by not addressing part of the job posting? Is there a professional way to make it clear that I love mocking Paris Hilton around the water cooler?

Thank you oh Amalah!

While using obvious, outright humor in a cover letter can be risky (if blogging has taught me anything is that you can accidentally offend ANYONE with ANYTHING), it definitely sounds like your cover letter could using a little punching up, a little creativity. Those strictly by-the-book letters are not going to make you stand out these days, when HR departments are getting stacks and stacks of them. Your experience and skills may be impressive, but they may not be enough to make you truly unique.

And when you’re sending out hundreds of letters and resumes, sometimes…that shows, a little bit, in your letter. I lost my job after 9/11, after the dot.coms went dot.boom, and I was completely unaccustomed the the Brave New Job Market of the time. I mean, I used to get interviews WITHOUT a cover letter at all! For writing positions! I didn’t even officially have a college degree yet! But if I stuck my resume out the window with enough technical buzzwords on it, demonstrating that I did indeed understand this double-u-double-u-double-u-dot Internet stuff, I could at least earn the right to show up and embarrass my under-qualified self in person.

Not so, once I really, REALLY needed a job. I wrote up a cover letter using some boring online template thing, a letter just like I’d been taught to write in college, and sent that sucker out over and over again. Sometimes I just swapped out company names and job titles, with cursory edits to include the most relevant experiences and skills. It probably reeked of a form letter and put hiring managers to sleep. I did have a couple versions of my resume (for technical writing, general editorial, marketing, etc.) since I was too terrified to care too much about a specific career path anymore. But as the weeks ticked by and the phone stayed silent, I realized that I needed a new approach.

So…I started writing custom cover letters for every. Job. Posting. I replied to. Like you’re supposed to do. I sent out fewer resumes per day and week, but quality over quantity seemed like it was worth trying. A few things I learned from my experience (and later, when I landed my dream editor job and actually became the interviewer/hiring manager myself):

1) Don’t just read and respond to the job posting. Research the company, as if you’ve already landed the interview. Spend time on their website. Make sure you have a clear idea of what they do/sell/produce. This will also help you gauge what KIND of cover letter will be appropriate. Are they a big Fortune 500 with a conservative business culture? A law firm? Best to stick with a short, professional letter. Are they a small innovative design firm with a ping-pong table and an emphasis on being “cool?” Scrap the traditional letter and send something more creative.

2) On that note, incorporate the company into your letter. Not just “my previous experience with blah, blah, blah is relevant to your needs because blaaaaaah.” Maybe include a paragraph about your experiences with their products, about something they’ve done as a company that’s inspired you. Make sure your letter suggests that this is a job you want because you really want to work there and you know you would kick ass at it, instead of: This Apparently Relevant Job Showed Up On My Monster.com Auto-Search Email Alerts.

3) AVOID THE MEANINGLESS AND INANE. Oh, my God. The number of boring cover letters I read that opened with either “Dear Sir/Madam, My name is 5) Appropriate creativity will get you noticed. My company published subscription-based monthly financial newsletters. I knew that we weren’t the dream job for entry-level editorial assistants. Most of them thought of “publishing” as books or Vogue or The Washington Post. And a lot of bland, bored cover letters told me that. So if, say, someone took the time to write their cover letter and resume IN THE FORM OF A NEWSLETTER (true story!), you KNOW they were getting called in for an interview, even if other candidates were a bit stronger “on paper.” Other ideas I’ve heard involve writing a Top Ten Reasons Why You Should Hire Me list, or sending your letter and resume packaged like the company’s product. (Specifically, inside a cereal box that an ad firm represented, and the letter opened with “It’s true. I’m a better prize than a secret decoder pin.”) Sense of humor? Check!

Of course, it’s risky. “Noticed” does not equal “hired.” You’re pulling a stunt and it may rub an grouchy HR person the wrong way. They might assume you’re trying to gloss over a deficiency in your education and experience…or they may send your stuff right over to the hiring manager in a “dude, you’ve GOT to check this out” kind of way. Which…might be a little farther than your resume would have made it otherwise. If you aren’t getting any interviews to begin with, you might want to gamble a little bit, since what else have you got to lose?

(Besides being the next Aleksey Vayner. Tip: Don’t submit anything that could end up on YouTube.)

Humor in a cover letter doesn’t have to be wacky, though, or uber-obvious. It just…comes through, when you’re writing something that you’re genuinely excited about. I mean, the email that you sent to this advice column clearly conveys a sense of humor, no knock-knock joke or a naughty limerick required! And I bet you just WROTE THAT, all by yourself, instinctively knowing how to hit that right blend of funny/interesting and get your question plucked out of a hundred others.

Instead of worrying about hitting the “sense of humor” bullet point directly, try scrapping your current (possibly dry and getting a little form-ish?) letter outline and start writing them from scratch for each job you apply for, in a more natural tone, sans any over-thinking.

I know that job-hunting can be soul crushing. Oh God, I know. And sometimes you start putting up natural defenses to keep the rejection and disappointment from becoming too much. And sometimes this shows in your writing, and unfortunately, no one wants to hire someone who already sounds detached, jaded and totally bored with themselves. Let yourself get excited about these jobs and companies and your writing will probably reflect that excitement… AND something a little closer to your actual personality rather than your business-suit-wearing professional alter-ego.