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When I was a Fellowship Program Manager, I saw my share of bad cover letters. There was the one where the student told me how much she wanted to work at Greenpeace (I had no connection to Greenpeace). There were the super generic letters, the ones that professed undying love and loyalty, and the ones that went on about how this role fit perfectly into someone’s five-year plan—with no mention of if that person could, you know, do the job.

While common mistakes can sink an application, when a letter showed inexperience more than anything else, I tried to put myself in the candidate’s shoes. It took me years to hit my groove, and my first attempt was full of rookie mistakes.

In the spirit of full disclosure, here are three lessons you can learn from my first, awful attempt at a cover letter—that I still keep in mind to crush it today.


1. The First and Last Paragraphs Aren’t Formalities, They’re Real Estate

I opened my letter with some variation on, “I am writing to apply for the position of [title] at [company name]. I possess relevant administrative experience and I am eager to contribute to [organization], which makes me an excellent candidate for this position.” To close out, I’d write: “My references are available upon request. Please let me know if I may provide any additional information.”

Now, for a short quiz:

  1. True or false: All of those lines would be true for any given applicant. (Answer: True.)
  2. True of false: The cover letter is the place to say the exact same thing as everyone else, because you don’t need to stand out, and you can go on for as long you’d like. (Answer: False.)

Yes, I’m sure there are worse things you could write. But what hiring manager thinks, “Let’s go with the forgettable candidate who plays it safe and didn’t tell me very much?” It’s always scary to take a risk, especially when you’re applying for a job, and especially when you’re new to—or out of practice from—writing cover letters. But it’s also ballsy and will make you a more memorable candidate, which improves your chances of moving forward.


The Fix

Instead of thinking about what you’d classically write to bookend your cover letter, imagine you were giving an enthralling speech. You’d be more likely to open with a story or a stat and close with a call to action. So skip the generic paragraphs, open with lines like these, and close with lines like these.


2. It’s Not a Love Letter

Yes, one of ways to stay stoked during a job search is to remember that you could work at a company you’ve always been obsessed with—the kind of company that makes you call your parents and update your Facebook status and feel like a really big deal.

But no, you don’t want to go all Carly Rae Jepsen on the hiring manager.

First, if the company is so cool that everyone dreams of working there when they grow up, then it’s in a lot of cover letters (see: not wasting space). Second, there’s always the risk that you’ll take your love too far and get a little creepy, or at least overly informal (think: “I follow the team on social, and along with doing great work, I’m all in on sake bomb Thursdays!”).

Third, and here’s where I screwed it up: When I spent two paragraphs detailing how I loved the company’s mission, and its website, and its materials, and its latest YouTube video, and its latest program, and its use of photography; I ended up with just a few lines to share my qualifications. In the end, I included almost no information about why I’d be a great hire (and obviously never heard back).


The Fix

A much better way to demonstrate your love for the company—and sell your skills—is to show (not tell) the hiring manager that you get it. Write your cover letter in a tone that matches the organization’s communication. Discuss a recent initiative or event or something you’ve noticed that you find particularly appealing. Point out areas for improvement in a product you regularly use. All of these strategies indicate that you didn’t find the organization this morning, but also allow you to showcase your observations and skills.

3. No Letter Can Save You From Applying to the Wrong Job

Let’s step back and look at the big picture for a moment, because my mistakes weren’t just some filler lines here and some odes to the company there: Often times, I was applying to positions I was sorely underqualified for.

In a lot of ways, it makes sense. First, you’re told that you’re going to have a lot to learn when entering the working world, but that you’re up to the challenge. Second, mid-level and senior-level positions sound so much more exciting than their entry-level counterparts. So, why not throw your hat in the ring?

Because hiring managers can see right through lines like: “I am a fast learner and while I’ve never run a social media department, I love Facebook, and I would look forward to studying the best campaigns out there and implementing best practices.”


The Fix

If instead of listing how your experience will translate to the role, you’re listing how it prepared you to study up, it’s a pretty good sign you’re in over your head—and your letter shows it. Remember, the job search process can be long, and you want to save your energy (and that letter to your dream company) for a gig you have a shot at!

If you’re not sure whether you’re reaching (which is good), or over-reaching (which is probably just a waste of time), check out this article by Muse writer Katie Douthwaite Wolf. It discusses how you can compensate in your application if you’re just a little underqualified. But, if this isn’t you, and you are years, degrees, or language proficiencies away from the requirements, apply to a role where you can build skills—and revisit this one down the road.



Part of improving your job search skills is learning from experience—yours and others. So, if your cover letter game seems a little stale, try these tips out and maybe even dig out an early version of something you wrote. Laugh, wince, and then see what you can improve on.