Your cover letter sucks

Q1 2023 was a quarter of bad news.

Tens of thousands of tech employees are being laid off every month.

It’s happening outside of tech, too, with McDonalds, Disney, and many others downsizing departments and axing entire divisions.

Anecdotally I’ve noticed some companies on LinkedIn saying that when they’re opening roles, they’re getting swamped with applicants. While unemployment is still low, some fields are going to face stiff competition right now. In order to get an edge, you need to stand out in the hiring process.

This can be a tough task.

Today I’m going to share how I once stood out in a crowded field. I’m sharing my actual cover letter (and I promise you, it’s real), as well as a few tips for making the modern “standardized” process more human.

2023 feels a lot like 2009-2010

Today most folks know me as the Silicon Holler guy who founded a social commerce company in Kentucky. No one could have seen that coming a decade ago, me included.

I took an unusual path to get here.

In college, I thought I was going to be a journalist. I had no doubt, really—I thought it was my life’s work, and even remember foolishly telling my girlfriend (now wife) that it was my calling. I felt the duty to serve as a journalist was bigger than me. I was so dedicated to storytelling that to think of doing anything else in 2008 seemed crazy.

I did an internship every summer in college. In 2008, I was a video intern at the Lexington Herald Leader, which was a phenomenal newspaper at the time. By the time my internship ended, dozens of journalists had been let go. The writing was on the wall. The smell of death was in the air.

Still, I finished my senior year focused on being a journalist. I earned my journalism degree and graduated during the Great Recession in 2009. Journalism jobs were hard to find. I applied to 40 photojournalist roles, and I heard back from two:

The New York Times said no thanks.

The Memphis Commercial Appeal offered me a spot as a contract freelancer (full-time with no benefits).

I took the Memphis gig, but ended up leaving Memphis in 9 months for a lot of reasons we’ll leave dormant today. I moved to Louisville, Ky., and was a freelance photojournalist for the next 18 months while founding a wedding photo agency. The wedding money was not bad, and I actually enjoyed the work. I was making more money with my own business than most of my friends who worked at small newspapers.

Still, I was young and didn't have the business chops yet. I also realized that the only way for my agency to make more money was for me to work more or charge more. I honestly just wasn’t talented enough to justify the higher rates and I wanted more stability so I could be comfortable (OK I admittedly also wanted to kayak and fish more on my weekends instead of hanging out with drunk groomsmen).

Once again, I set off applying to dozens of jobs in advertising, none of which even got me to an interview. I had one major problem.

I was not qualified.

A break came, and I had to stand out

Finally I got a chance with a local ad agency, and I knew I only had one shot to catch their attention. I had no real experience to speak of, and I didn't have a degree in marketing. But I had done my own social media marketing for my wedding business, and in college I actually brought our college newspaper into the social media landscape under the now outdated title of “Mixed Media Editor.” I pulled all of that into a résumé crafted just for this role, and then researched the company’s culture. It was fun and lighthearted. So with that in mind, I sat down to write my cover letter.

And it was the most ridiculous, show stopping cover letter I could muster.

Here it is, in full:

————

Dear [Hiring Manager],

Look, it’s like this:

Pretty much anyone can figure out how to make a Facebook page, and even my dad has a Twitter account. Actually, I would be willing to bet you could give a monkey a computer and with enough time even he could compose a Tweet. With the low cost of bananas, the idea of a Tweeting monkey at the office might sound efficient and acceptable—oh, and of course, entertaining.

But I smell better.

Actually, I do a lot of things better. While I don’t have a degree in marketing, I have been selling myself since graduating college. My entire income is based on how well I market my company. In my first year in Louisville I created a photo agency that was voted among the city’s best photographers and videographers, and it was all due to my ability to connect.

I don’t believe success can be contained within 140 characters, but it can certainly start there.

I look forward to hearing from you,

Brad Luttrell

————

It worked.

After a ridiculous four or five interview process—including meeting with the board—for an entry level role, it worked. I got the job.

Looking back, I can see I undersold myself. I had worked in social media and blogging since 2005. But much of that felt like fun, not work. Still, with so little experience presented, my character stood out.

It was a bit of "This guy is just crazy enough he might be able to pick this up."

Or...

"Well, he isn't formally trained, but he clearly can be creative."

If you're applying for a stretch position—which is the only position that can make you grow—go bold on the cover letter and application. For most small to mid-sized companies, It is more important to be memorable than professional. If you want help getting a role at a Fortune 500, you are reading the wrong newsletter.

When you have the option to stand out—take that chance.

3 tips for standing out in the hiring process

1) Stop regurgitating your résumé in your cover letter

Most people will sit down to write a cover letter, and they will share the narrative version of the résumé. It’s a dreadful approach. Your résumé is supposed to be the concise story of your work history because it’s efficient—don’t give them an inefficient version, too. Your cover letter should show your personality or pull stories from your past that showcase why you’re a great fit. Go bold, be memorable and tell the stories that make you a gem.

2) Don’t rely on professional experience alone

All-too often, people disregard their relevant personal experience. Hiring managers love passion, so if you’re applying to a job and have a passion for the field, that needs to come out in your cover letter, even if it’s not professional experience. If you’re applying for a marketing role at a large brewery, and have been a home brewer for years, that’s relevant. If you are trying to get on with a direct-to-consumer cookie company, and grew up baking cookies with your mom, share it. These personal tidbits cuts through the banal barrage of applications most hiring managers will have to review, so don’t be afraid to go personal.

3) Never forget the power of an inside man (or woman)

This tip actually will work at a small company or Fortune 500 alike. If you know someone within the company, they can likely give the hiring manager a heads up on your application and get it pulled to the top of the pile. I recently wrote a newsletter about how to do this, and it totally applies here. Most hiring managers hate hiring—it sucks. If someone can give them a heads up on a quality applicant who may work out and ease the pain of the process, they’re going to take that opportunity every time. Don’t be afraid to call in favors.

Who I’m listening to: John Prine (RIP, gone 3 years ago this week)

What I’m reading: “Hail Mary” by Andy Weir

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