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Advice / Job Search / Cover Letters

I've Read Over 300+ Cover Letters and This Is How I Decide if It's Good or Bad Within 3 Minutes

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I’ve read a lot of cover letters throughout my career. When I was a fellowship program manager, I reviewed them in consideration for more than 60 open positions each year. So I saw it all—the good, the bad, and the standout cover letter examples that I can still remember.

As a result, I’ve become the go-to friend when people need feedback on their job applications. Based on my own experience putting people in the “yes” (and “no”) pile, I’m able to give these cover letters a quick scan and immediately identify what’ll turn a hiring manager off.

While I can’t give you insight into every person’s head who’ll be reading your materials, I can share with you the feedback that I give my own loved ones.


1. The Basics

First things first, I skim the document for anything that could be disqualifying. That includes typos, a “Dear Sir or Madam” or “To Whom It May Concern” salutation, or a vibe so non-specific that it reeks of find-replace. I know it seems harsh, but when a hiring manager sees any one of these things, she reads it as, “I didn’t take my time with this, and I don’t really care about working here.” So, she’s likely to pass.

Another thing I look for in this initial read through is tone. Even if you’re applying to your dream company, you don’t want to come off like you think someone entertaining your candidacy is the same as him offering you water at the end of a lengthy hike. You don’t need to thank the hiring manager so incredibly much for reading your application—that’s his job. If you align considering your application with the biggest favor ever, you’ll make the other person think it’s because you’re desperate.

So, skip effusive thanks and demonstrate genuine interest by writing a cover letter that connects the dots between your experience and the requirements of the position. Telling the reader what you’ve accomplished and how it directly translates to meeting the company’s needs is always a better use of space than gushing.


2. The Opening Sentence

If your first line reads: “I am writing to apply for [job] at [company],” I will delete it and suggest a swap every time. (Yes, every single time.) When a hiring manager sees that, she won’t think, “How thoughtful of the applicant to remind me what I’m reading!” Her reaction will be much closer to, “boring,” “meh,” or even “next!”

Compare it to one of these statements:

  • “I’ve wanted to work in education ever since my third grade teacher, Mrs. Dorchester, helped me discover a love of reading.”
  • “My approach to management is simple: I strive to be the kind of leader I’d want to work for.”
  • “In my three years at [prior company], I increased our average quarterly sales by [percentage].”

See how these examples make you want to keep reading? That’s half the battle right there. Additionally, it makes you memorable, which’ll help when you’re competing against a sea of applicants.

To try it out for yourself, pick a jumping off point. It could be something about you or an aspect of the job description that you’re really drawn to. Then, open a blank document and just free write (translation: write whatever comes to mind) for 10 minutes. Some of the sentences you come up with will sound embarrassing or lame: That’s fine—no one has to see those! Look for the sentence that’s most engaging and see how it reads as the opening line for your cover letter.

3. The Examples

Most often, people send me just their cover letter and resume, so I don’t have the benefit of reviewing the position description. And yet, whenever a letter follows the format of “I am skilled at [skill], [skill], [skill], as evidenced by my time at [place].” Or “You’re looking for [skill], and I am a talented [skill], ” I could pretty much recreate it. Surprise: that’s actually not a good thing.

Again, the goal isn’t just to show you’re qualified: It’s to make the case that you’re more qualified than all the other applicants. You want to make clear what distinguishes you, so the hiring manager can see why you’re worth following up with to learn more. And—again—you want to be memorable.

If you write a laundry list, it’ll blend into every other submission formatted the same way. So, just like you went with a unique opener, do the same with your examples. Sure, you might still include lists of skills, but break those up with anecdotes or splashes of personality.

Here’s a real, two-line excerpt from a cover letter I’ve written before:

If I’m in a conference room and the video isn’t working, I’m not the sort to simply call IT and wait. I’ll also (gracefully) crawl under the table, and check that everything is properly plugged in.

A couple lines like this will not only lighten up your letter, but also highlight your soft skills. I got the point across that I’m a take-charge problem solver, without saying, “I’m a take-charge problem solver.” Plus the “(gracefully)” shows that I don’t take myself too seriously—even in a job application. If your submission follows the same list-type format all the way through, see if you can’t pepper in an example or anecdote that’ll add some personality.



You want your cover letter to stand out for all the right reasons. So, before you click submit, take a few minutes to make sure you’re putting your best (and most memorable) foot forward.