The Top 10 Cover Letter Fails Ever (as defined arbitrarily by yours truly, MJD blogger)

Fail RoadDepending on who you ask, sending a cover letter for a job application is either outdated and hopelessly dumb or is the defining factor for whether you get the job. Of course, if your cover letter looks like one of the ten atrocious ones below, you’ll probably agree with those who hold the former opinion.

I’ve been collecting my favorite examples of egregious cover letters for years. From simple yet unfortunate typos to bigger issues, these ten, culled from the Web and from applications I’ve received, are among the worst of the worst.


#10: I sh*t you not
I’m looking for work because even though my company was profitable last year, this year they are expecting a large defecate.

Sent to ad agency Killian Branding, this line underscores why you should never rely on spell-check to proofread your letters. Have a friend look over your work before you send it off.


#9: I prefer oysters, myself
Other skills I’ve learned are, being a proficient multi-tasker, handling detailed oriented documents with care, handling stressful situations with a clam demeanor, and joggling different projects with time management.

Another lesson for would-be hires: TELLING about your skills is much less effective than showing them. In this case, this supposedly detail-oriented applicant made at least four mistakes in one sentence, depending on how you count, undermining his or her own claims. (Source)


#8: This was for a job that specifically said the hire must be based in Washington, D.C.
My name is [redacted] and I was hoping I could still submit and work remotely, as I never lived or be in DC. Please look at my resume and accomplishments to see that I have excellent expertise working on my own with no supervision.

While some say you may have nothing to lose by applying when you clearly don’t meet the most basic qualifications of skills, experience, or in this case geography, you also have very little to gain by ignoring explicit instructions. This letter came in for a job I posted and went straight into the trash.


#7: Same job, different applicant.
Hello from California…

Are you even reading the ad?


#6: Is this a job application or a romance novel?
Taking notes and pictures on the floor of the Senate Finance Committee boardroom with an H&M skirt daintily covering my folded legs. This is Tim Geithner’s third testimony on the Hill this week alone, and his eyes dart around the room more than usual… It is at this moment I realize that reporting and I were meant to be. He has had his practice, I have had mine — and it all comes down to this moment.

From our friends at FishbowlDC…I have no words.


#5: 35 pull-ups? You’re hired!
I continually challenge myself…that semester I achieved a 3.93, and in the same time I managed to bench double my bodyweight and do 35 pull-ups.

This letter went viral over a year ago and I still can’t figure out what pull-ups have to do with investment banking.


#4: A letter from a prominent undergrad
I am a prominent undergraduate student in the communication studies department here, and from time to time even assist graduate students with brainstorming and analysis.

What does that even mean? The folks at Ragan couldn’t really figure it out either. It looks like a new grad trying to make up for a lack of experience. She’d have been better served to focus on her internships (she had one at a local radio station); this padding didn’t impress Ragan.


#3: Another entry in the “novel rather than cover letter” category
In every regard, my qualifications appear to be consistent with the desires expressed by your advertisement, and based on the voice of the Business Insider blogs and my critical evaluation of your newsroom and its inhabitants, I really think that I was meant to be a Contributors Editor for Business Insider.

Yep, someone sent this to BI. The BI of short, Huffington Post-esque slideshows and somewhat breathless writing about the stock market? Yeah, they’re going to love someone who writes the purplest prose this side of Bulwer-Lytton. Takeaway: Know your audience. And remember Mark Twain’s quip about never using a “five-dollar word” when a cheaper one will serve the same purpose.


#2: Who are you? Is this enterprise ashamed of itself?
Craigslist advises against providing personal information to anonymous posters, especially those using only a CL e-address.  Common sense concurs.  Why the secrecy?  Who are you?  Is this enterprise ashamed of itself, or ashamed that it’s seeking writing help?…If you’re paying professional rates for professional work;
If you’re adults;
If you’re funded, and not secretive about it
…then please reply with contact information and some of the kinds of information you had to present to get funded.  I’ll be glad to reply with a CV and examples of work published or aired. 
Every good wish,

This was sent, perhaps obviously, to an anonymous Craigslist job ad for freelance contributors. Look, I get it. Anonymous job ads are ridiculous; freelancers do often get the short end of the stick. But starting the relationship out on a combative note is not going to make you any friends. And I love the “every good wish” at the end. It’s like ordering a diet Coke to go with your Big Mac: pointless.


And the number-one cover letter fail of all time:
#1: “I wish to…appeal to your irrational masculine avatar”

Say what? This would-be law clerk’s letter is shocking in so many ways and it’s stuff like this that makes hiring managers say they’d rather not get a letter at all. With lines like “My homogeneous person was slapped right in the face” and “Hubris, however, was the only Greek concept I truly evinced during a near-graduation retrospection of my college years,” how could this guy not get hired? Listen. We media folk (and sometimes law clerks) have to emphasize storytelling in our cover letters. But the stories have to say something. All this one says, once you strip out the BS, is “I went to college, graduated, and went to law school. Now I need a job.” Good one, buddy. As the original poster says, the best line of the letter may just be, “I am extremely self aware.”


Do you need help with your cover letter and want to avoid seeing yourself on one of these lists? Funny you should ask; I’ve written an e-book on cover letters for media pros. It’s on Amazon for your Kindle/tablet/phone/computer or on iTunes for your iPad. At $6.99, it’s not super expensive. You might like it!