The Strangest, Funniest (and Worst) Resume Content and Cover Letters

James O'Brien

Selfies. Professional theatrical head shots. Writing samples that turn out to be plagiarized. If you speak to human resources professionals, you’ll find that job applicants send in all sorts of inexplicable materials.

“This is just the tip of the iceberg,” said Monica Guzman, chief operations officer at Konnect Public Relations. She’s seen the selfies, and more. “In addition to these, I have also gotten all the typical bad resumes with misspellings, content that is obviously catered to other jobs and has nothing to do with positions available at our agency.”
It’s not just the glaring typos, either.

Sometimes, when the envelope is opened, a hiring manager can only scratch his or her head and wonder. And so, in the spirit of avoid at all costs, check out the following examples of odd, weird, and simply misguided resume and cover letter content — each supplied by folks who’ve been in the trenches long enough to see it all.

Terrifying the hiring manager. Barry Maher, an author and speaker who also consults in the hiring world, once received a cover letter from an application for a position at a charity. The applicant had already gone to the organization’s website and found the names of and contact info for everyone on the nonprofit’s board. “Cutting out letters from a newspaper,” said Maher, “he sent each board member a series of mailings. The first had just his first name, John. The second read John Smith.” Following that, subsequent missives added a word each: so, the third letter read John Smith is; the fourth and then the fifth read, John Smith is going to. And then the sixth and seventh letters completed the sentence: John Smith is going to blow you away! “Which is when the police showed up at his door,” Maher said. Turns out Mr. Smith never got his chance to interview and explain that he only meant his expertise was going to blow them all away.

The ‘do-it-or-else’ approach. Pitching your worth can be a challenging prospect, but some applicants take the attempt a little too far. Some time ago, when Mike Scanlin, chief executive officer at Born To Sell, worked in the venture-capital world, he “received a business plan that had a photo of an empty parking lot on the cover,” Scanlin said. “Below the photo was the caption ‘invisible car’. The guy wanted to make a car covered with little cameras and screens that would render it invisible.” And here’s the kicker: “On the front of the business plan was a sticky note that said, ‘if you don’t fund us then we’re taking this to the Iraqis'” Needless to say, the proposal didn’t work out. Safe to say, it’s never a good idea to threaten your recipient with international enemy-combatant implications.

When the medium is the (wrong) message. Just because the job will get your hands dirty doesn’t mean the application process should be an untidy affair. “The strangest resume I ever saw was one that I received when I was a division manager for an industrial equipment distributor,” said Jim Dalton, who now works with his wife in the family pottery studio. “We advertised for a technician who would travel to customer sites and service our equipment. We emphasized in the ad that communication and technical skills, and experience, were absolutely necessary. I received a multi-page resume handwritten on spiral notebook paper that had been torn out. It went immediately into the trash.”

One key takeaway? Keeping your cover letter and resume out of the garbage bin takes only a little bit of common sense, but that doesn’t mean you should never use your creativity when reaching out in a competitive market. For example, the most creative and interesting resume that ever came to Jodi Donner, responsible for outreach and social engagement at Wakefield Media, landed its sender a job with the company. “It was a crossword puzzle encompassing his positions, with skills as the clues,” Donner said of the applicant’s tactic. “It immediately caught our attention, and showed us that he was detail-oriented, clever, and worth a call. He’s been working for Wakefield Media for just over a year, now.”

So, don’t be entirely afraid of standing out, just try not to cause a law enforcement incident along the way. Take heed of the warnings packed into the examples in the above list, and then craft a resume and cover letter that will get you noticed — without getting you into trouble!

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