I’ve never been bothered by the existence of resumé-writing services — you know, people who will critique your resumé (or even write the whole thing for you) for a fee. It seems, at first glance, like cheating — getting someone else to do your work for you! — but, think about it: a resumé is, at its base, a fairly objective thing. It’s simply a factual history of your career. Resumé writers aren’t falsifying any information. They’re not making up jobs or accomplishments (well, they shouldn’t be; if they are, go use a different service, please. One with scruples); they’re simply helping job seekers catch the attention of employers by deploying the right keywords to get through ATSs and other such hurdles.

An analogy: you are a new medicine, and the resumé writers are marketing you. They aren’t falsely claiming anything about your abilities as a drug; they’re just presenting your abilities to the public in the best possible language.

But cover letters are a different story. Unlike resumés, which are about your factual, verifiable work history, cover letters are more about you as a person. They are a way to introduce yourself to a company, a way to give your potential employer a feel for who you are. This is why I’ve always been much more wary of services that will write your cover letter for you.

Imagine you are at a party, and Person A is making the rounds, introducing themselves to everybody at the party. Except, here’s the weird thing: Person A actually isn’t introducing himself. He isn’t saying a word. He doesn’t interact with anybody. Instead, he is following around another  guy, Person B, who is doing all the talking for him. Person B is telling everyone else at the party about Person A, while Person A stays silent the whole time, never actually demonstrating anything about his personality.

I ask you: did you really meet Person A, or do you just know what Person B has told you about him?

This is how I feel about cover letter services: they are the Person B to the candidate’s Person A, speaking for the candidate, but never letting the candidate show us who they really are.

So, yes, I feel like cover-letter-writing services might be a little disingenuous: if the point of a cover letter is to introduce yourself, why are you letting other people do all the talking for you?

Exceptions to the Rule

As you’ve no doubt noticed, my whole argument against cover-letter-writing services comes from gut feeling, intuition, and analogy. I’ll be the first to admit: these aren’t the strongest of argumentative foundations, though I do think my case against cover-letter-writing services is fairly solid.

I have to admit, however, that I could be wrong (which, I think, is okay: what fun is an essay written by a guy who has everything already figured out?). Perhaps cover-letter-writing services could be useful.

You may know from previous posts that I often peruse Reddit to keep tabs on employment news. This past weekend, in one of the job-related subreddits, I came across a post about a cover letter generator. It is exactly what it sounds like: a service that generates cover letters for you.

Obviously, Cover Letter Tutor, as the generator is called, is different from a cover-letter-writing service, as you aren’t hiring somebody to write a cover letter for you. Instead, you follow the website’s step-by-step instructions, fill in some boxes, and — presto — you have a cover letter.

I used the Cover Letter Tutor to create a mock cover letter for myself if I were applying (once again) to write for recruiter.com. Here’s the end result:

July 14, 2014


1533 New Britain Avenue Second Floor East Farmington, CT 06032

Re: Staff Writer Position 

To Whom It May Concern,

I believe I am a good candidate for the staff writer position at Recruiter.com because my extensive background as an HR technology writer has prepared me to create relevant, engaging content on a daily basis. 

In college, I oversaw the opinions section of a daily newspaper, which has helped me to develop my editorial skills, as well as work with a team of fellow writers. My time spent as a freelance writer has not only sharpened my writing skills, but has also taught me how to work with a variety of clients and coordinate my schedule to accommodate heavy workloads in a fast-paced environment.

I believe I could contribute quite positively to Recruiter.com, and I await the opportunity to prove it. 

Thank you for your time and consideration,

Matthew Kosinski

Obviously not the best cover letter in the world. You can tell from the stiffness and the de rigueur nature of the prose that I used a computer to help me write this — there’s no real human warmth in it.

But I’m not here to bash Cover Letter Tutor. I’m actually here to point out that it’s a really good tool for people who are not terrible sure about how to write a cover letter. See, unlike getting someone else to write the letter for you, Cover Letter Tutor walks you through the basics step by step. While I don’t advise actually sending the end product to any companies, Cover Letter Tutor is a good way to learn about the structure of a good cover letter.

Ideally, I think people should stray away from cover-letter-writing services that do the work for you, for all of the reasons I outlined above. But for new members of the workforce, who are still uncertain of how to write cover letters, I think a tool like Cover Letter Tutor is great.

To get the most use out of a cover letter generator like Cover Letter Tutor, here’s what I would do:

  1. Use the website to generate a cover letter.
  2. Take the end product to someone in your life who has experience with cover letters — a professional, a friend, a relative, a mentor, what have you.
  3. Go over the generated letter with your cover-letter mentor. Get their feedback on personalizing the cover letter without sacrificing professional dignity.
  4. Use the combined knowledge of the cover letter generator and your real-life expert to make the best cover letter possible — just make sure you write it yourself, or you’ve learned nothing.

This advice is mainly geared toward newbie job seekers, as they are most likely to have little-to-no experience with cover letters. That being said, it doesn’t really matter where you are in your career — if you think your cover-letter writing needs work, then hop to it.

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