I let an expert tear my horrible cover letter to shreds — here are the mistakes I won't make again

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I hate cover letters.

They're long. They're boring. Unlike résumés, you can't just blast them out to multiple companies with minimal editing.

I always feel like mine sound super fake, even when I am genuinely excited about the job.

But when I was applying for jobs in my senior year of college, I did my best to shake my bad attitude by researching what makes a bomb cover letter.

A lot of the advice I got — on the internet and from people I know — was dry, vague, and rather contradictory: "Make it half a page, tops; tell a story; don't get fancy; staying formal is your best bet; contractions are unprofessional; keep it short and sweet!"

As my various application deadlines loomed, I actually dug up an old cover letter that I'd submitted to an internship junior year. I figured that I'd be lazy and plug in some new names and details (yeah, I now know that's a bad idea) or at least use the bare-bone structure to write some new cover letters.

But ... that's not what happened. My old cover letter was completely unsalvageable. Inexcusable. A three-page, self-focused monstrosity. And I'd sent it out for other humans to read.

So I figured I'd ask an expert to go over my terrible letter and provide concrete reasons on why it's a train wreck.

Amy Adler, a certified master résumé writer, management coach, and CEO of Five Strengths, went through paragraph by paragraph and gave me some feedback.

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Adler also provided the following helpful tips on how I could've improved this particular cover letter. (Other than burning it and starting over.):

Don't wait to tell your story

This cover letter was more like a weird, rambling history of my experience on my college newspaper than like ... well, a cover letter.

But Adler says I kind of had the right idea. It's not a bad idea to set down your "deep history" in writing. Think of it as the prequel to your cover letter.

"You will learn more about what makes you tick, but you don’t have to show it to your hiring manager," Adler says.

You can save this prequel and pull it out when you need to apply for a job, saving time on brainstorming your accomplishments and experiences.

Just don't do what I did and send this draft instead of an actual cover letter. 

Don't stumble out of the gate

I got off to a weird start in my cover letter, which I addressed to "Dear To Whom It May Concern." 

Yikes. I think that was a typo? I hope that was a typo. 

Plus, I also included a line introducing myself by name, which was already clear from my signature and accompanying résumé.

Things got worse from there. 

Don't forget to include a clear objective

In my case, Adler says that she couldn't actually figure out what I was even applying for.

I didn't mention what I role I was going for at the beginning of my letter. Oops. 

It's probably a good idea to start with a clear objective. Hiring managers aren't mind readers.