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Are You Brave Enough to Send These Risky Cover Letters?

You’ve just found that perfect job opportunity. You’re networked your way to a contact person, brushed off your portfolio and polished up your resume. Now, it’s time to create the perfect cover letter. You’re torn between a desire to come off as professional and employable, and a need to stand out from the pack and grab the attention of the hiring manager.
cover letters
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Is it possible to do both? The answer, as always, is that it depends. While risky, in the right hands, daring cover letters can sometimes accomplish more than the standard approach. The key is to know why they work — and carefully gauge your audience (and the corporate culture) before sending.

Here are a few examples of risky cover letters done well:

Put a Personal Face on a Cover Letter

Sitting in an evacuation shelter in Florida while Hurricane Irma was bearing down on his Key Largo home this past September, hospitality industry worker Mark Frances penned an unusual cover letter, which he then posted on LinkedIn.

“…I’ve decided this time to make a deal, and to re-write my cover letter to prospective recruiters,” he explained in his column about the letter. “I’ve decided that I will tell you about me, yes seriously….about me!”

Here’s an excerpt:

I have lived on three continents, in eight countries and 17 towns. I pack light and I move fast. Nothing scares me. I have worked in remote hostile locations and easy city centers. I have negotiated with more Unions (and some tribes) in more countries than most, and have learned a tactic for every negotiation. I have won international awards, and made catastrophic mistakes. I have landed multi-million dollar pieces of business, and ruined a sunset dinner or two. I have woken up late sometimes, and worked late most of the time. I have laughed. A lot. I have cried when I have lost. I have watched with pride when my team members have succeeded. I have won awards for my work, and taken many kickings for the things I have messed up.

I try to stay healthy, I try to be positive every day, I love as much as I can, and I would do anything for my kids. I have a small group of loyal friends who love me, love me through all my mistakes and through all my successes. I give my very best every day to everything I do, and as the great Curt Carlson said…I never ever give up.

The letter continued with more details about what Mark offers an employer, and what he would bring to the job.

Read Mark’s full cover letter on LinkedIn. 

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Show Your True Colors

At LinkedIn, Communications Director Gianna Rico wrote about the unconventional cover letter she penned to catch a great internship when she was just out of school. The job posting itself didn’t pull punches on its search for a quirky, talented new hire.

“What stuck out was the fact that the job listing itself was different from all the rest. It asked for a cover letter with personality, even saying that it would be good if you knew all the lyrics to Thrift Shop,” Rico wrote.

Rico chose to take this potential new employer of hers at their word, and gave them what they asked for: personality. Her cover letter began:

Okay, let’s be real. As a Graphic Designer, how can communications not be my jam? Pretty sure I was destined for a career in communications ever since I was the first one of my friends to figure out how to link all of my screen names together to form a massive buddy list … whaddup. As for Thrift Shop? Obviously I know all the words to it. Not only because I’m a boss, but also because I know for a fact Macklemore stalked my life to get inspiration for his lyrics…

And it worked! Rico landed an internship at an interesting startup company, and her career was born. She hasn’t regretted that personal touch to her cover letter, and in fact, recommends the approach.

“In the next cover letter you send, instead of starting off with a lengthy paragraph littered with those ‘buzzwords’ career counselors are always raving about, show the employer who you really are,” Rico said. “If there’s a fit, it’ll be obvious — to both of you, employee and employer.”

Read Gianna Rico’s full cover letter on LinkedIn.

Take a Risk to Get the Job of Your Dreams

In 2015, Josh Emberson really wanted to break out of his banking job and work for a cool startup company in the tech industry. He had been tracking Uber, and decided he was going to lay it all on the line with a cover letter he hoped would land him a position there.

“The posting asked for a copy of my resume and a cover letter outlining why I wanted to work at Uber,” he wrote at Breaking Bay Street. “After failing with a traditional cover letter at every other start-up, I took a risk and decided I would write a truthful letter about why I loved the company. When I sent my application off, I literally felt sick to my stomach and thought I had just made the biggest career limiting move of my life. About a week later, I got called for an interview. I was shocked.”

His cover letter begins on an unconventional, and even scandalous note:

15 years ago, I stood in a crowd with 15,000 other sweat soaked fans, the majority of us under the age of 18, under the hot August sun awaiting the band Rancid to take the stage. A roar let out from the crowd as the lead singer, Tim Armstrong took the stage. In a distorted slurred voice, he shouted out, “F%$k you, Toronto.” Energy in the air was atomic. He screamed, “it’s time for a change, and that change starts here today. Who is tired of being ripped off by the major music labels? It’s time we destroy these corporations together … music is for the people!” Within seconds there were 30,000 middle fingers in the air chanting, “F%$k the major labels.”

I will never forget the next forty?five minutes of my life. The crowd danced, partied, fought and screamed. As Bob Dylan once said “revolution was in the air.” …It was obvious the ways of yester year was not for these kids, and I NEEDED to be a part of this change.

That, he explained, was why he wanted to work for Uber.

“I want to be part of the revolution,” he wrote. “I want to be part of the change that has already started.”

Emberson warned that a risky cover letter is just that — a risk — and it could backfire for you. He also noted that the same strategy that worked for a tech startup probably wouldn’t succeed at an investment bank. It’s all about creating a cover letter that’s a good fit for the company.

Read Josh Emberson’s full cover letter at Breaking Bay Street.

Tell Us What You Think

Have you ever scored with a daring cover letter? We want to hear from you. Tell us your thoughts in the comments or talk to us on Twitter.


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