The Basics: Why I love cover letters (and why you should too)

Despite how much they're universally reviled, I love cover letters. They represent a great opportunity and you should take advantage.


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I get why people hate cover letters. Writing is hard enough but then you have to do it about yourself, to convince a stranger of how great you are, to be rejected or ignored going to be rejected? The task then goes from herculean to Sisyphean in its impossibility.

So people take to "the experts" or ChatGPT to help with the task. They include all the "right" keywords, mirror the writing of the job ad, and recap their milestones. They use all the intelligent synonyms that thesaurus.com suggests, piling on the action verbs and descriptors. They describe themselves as a hard worker, a quick learner, and as someone looking for a good team to work with. Yay?

Credit to anyone getting something down on (metaphorical) paper. Writing is hard. Writing in an unnatural or boring context is even harder. So finishing something at all is a feat in itself. That said, what I'm often looking over with clients is a boring wall of text that makes my eyes glaze over in even the 10 seconds I'm willing to give to that verbal oatmeal before offering my feedback.

The thing is, I love cover letters. I find them as fascinating as I do useful. I also think that there's so much Bad Advice on writing them that they lead to some very common pitfalls (more on this later). AI falls prey to those same tendencies but to give credit where due, ChatGPT has gotten much better with its latest version but its suggestions are still a bit bland.

Here are five reasons why I love cover letters (I'm sparing you the diatribe I seemingly always have at the tip of my tongue on the topic):

  • Introduce yourself. How many interactions do you get in life where you get to give a little preamble about yourself to lay out the context of your interaction? Not many. Online dating is the only other immediate example that comes to mind.

  • Provide context. You basically get to tell someone exactly what shade of rosy colored glasses they should be using when they're looking over your materials. Highlight your strengths in a way that makes your resume look even stronger.

  • Disarm your weaknesses. This ties into the above. It's possible you already have some ideas for why you might be rejected. What if you preemptively addressed those concerns? This isn't applicable to every situation and it doesn't mean you'll automatically become the best candidate, but transparency can answer some of those questions that might get you rejected from the get-go. It can also de-fang the surprise from the potential questions that might trip you up later. Maybe this is how you explain a resume gap, why you left your last company, or why you're making a career pivot. Without context you might be a no, but maybe this keeps you as a maybe.

  • Organize your thoughts. Cover letters can help you consider some of the questions that you should really have answered when you apply somewhere -why you, why this company, why this role, etc.. It's not that you need to manufacture something wholly unique for every application, but it's good to have your "elevator pitch" ready to go. ("I've been an IC my whole career, have only recently dabbled with management, and I think the well-known leadership/management training at Acme Inc. could help me to take that next step. I've also loved Acme's products since I was a kid.") It's important to know what you're trying to say before you write anything and this is a good way to determine what that is.

  • Practice. Cover letters won't be entirely unique (templates are your friend) and you're going to vary on just how much passion you can manifest for every company, but this is a good way to navigate through those different levels of interest. You might emphasize the company, the industry, the role, the process, or any number of other things depending on the situation, and cover letters help you work through those different angles, which can be helpful throughout the application process.

I don't genuinely think I'm going to change everyone's mind about cover letters with this piece. However, I think they represent a huge opportunity that I'm surprised more people don't utilize (or utilize to the extent they could). Hopefully I've at least helped to make them seem like less of a chore, or at least less of a useless one.

Writing is hard. Coming up with ideas is hard. If you need some help working out how to improve your message, describe your experience, or make your cover letters have more you and less ChatGPT in them, please reach out. I'm here to help.

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