Cover Letters for Fun and Profit, Okay Mostly Profit

Are there people who write cover letters for fun? If you are one of those people please let me know, I’m curious. Most of us write cover letter for-profit aka a job.

Over the past couple months, I’ve been looking for my next role. In addition to reaching out to my network, researching organizations and polishing up my resume this has also meant writing cover letters. From personal experience as a hiring manager and after researching what makes an effective cover letter I think it might be more important to realize what makes a terrible cover letter.

Terrible Cover Letters I Have Known and Loved

(or at least read out loud to a coworker)

You All Stink!

One of the most memorable cover letters I ever read was one in which an applicant wrote to tell us the entire premise of our organization was wrong. Since we were so wrong we should hire them.

Oh, were they applying to be CEO or something?

Nope, software developer.

We were sorely tempted to write back and explain why we were right, but we had probably already spent too much time on their application. So their goal of getting our attention worked, just not the right kind of attention.


When using recruitment software at first I didn’t require a cover letter but made it optional. I was getting a flood of resumes without cover letters, so I switched to making it required. Then I was getting a flood of resumes with “n/a” as their cover letter. I never once interviewed someone who put that in the space for a cover letter. My reasoning was:

  • If they don’t follow instructions in a job application process how are they going to be to work with?
  • They didn’t specifically want to work with my organization and I was hiring at mission-driven non-profits.

Excellent Attention to Detail

This really happens too often. People insist they are very detailed oriented but then have typos or other issues with their cover letter that could be caught by a spellcheck or Grammarly. I personally am afraid at this point to mention my attention to detail in a cover letter because of the potential of these issues. Also of all my personality traits, it is not my strongest, so I would definitely be highlighting something else.

I Don’t Have It Completely Figured Out

I do write a personalized cover letter for every job I apply. I try to make it interesting, show my personality and why I’m right for the job. I haven’t started attaching pictures of chickens yet, but maybe I should.

In the absence of the ability to collect real data such as A/B testing I simply do the best I can. I base this on research and experience, as well as remembering how much “n/a” as a cover letter annoyed me.


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