A reader writes:
I’m really not sure where to land on using AI to help with cover letters. I’ve seen a lot of conflicting advice ranging all the way from “no one wants to be bothered with a cover letter anymore” to “if I even smell a whiff of AI usage in a cover letter, it automatically goes into the reject pile.”
The job market is really bleak right now, and I’m trying to stay optimistic, apply diligently, and not overwhelm myself. Currently, I use the free version of ChatGPT to help me draft cover letters, and then I go back and edit them to sound more true to myself. I’m really not a big proponent of AI, and while I occasionally use it for work, I rarely use it in my personal life outside of job applications. The way I see it, if companies can rely on AI to scan hundreds of resumes and applications, then I don’t see why I shouldn’t also use it to my advantage. We’re in an employer’s market as it is, and I feel like if I tried to make time to write a personalized cover letter from the heart for every application that requested one, I would never make any progress and instead end up wasting a lot of valuable time.
But I’m also worried that maybe I have a hard time “reading the room” about AI usage because I work for a tech-adjacent company where it feels like almost everyone has drunk the AI Kool-Aid. I know at my office there is no shame in openly using AI to help us work more efficiently, and one of my executives (I’m an EA, for reference) even brags about her Gemini assistant. Now I’m stuck in this weird back-and-forth with myself about whether or not I should keep using AI to help me look for a new job, or if the AI-generated writing is genuinely off-putting to potential hiring managers and only hurting me more than helping.
Personally, I don’t want candidates using AI because I want to hear their voice and their writing, at least if it’s a job where written communication matters, but if it’s well-edited I shouldn’t be able to detect it anyway.
However, you sent me one of your AI-assisted cover letters to look at, and while I don’t think it screams “AI wrote this” … it’s also not a cover letter that’s going to strengthen your candidacy. It suffers from exactly what most cover letters suffer from: it just summarizes your work history and repeats things that are already evident from your resume, so it doesn’t add to your application and is squandering the opportunity of this whole additional page. So in this case, AI isn’t really relevant — or to the extent that it is, it’s only that AI has produced a blah cover letter that won’t boost your chances the way a better letter could.
I’m frankly not sure that AI can help you produce a good letter, at least not if you’re not giving it the right material to work with. The right material has to go beyond the contents of your resume and the job you’re applying for, because a good cover letter needs to talk about things that make you especially well-suited for the job without just regurgitating your resume. Once you come up with those things, you could in theory feed them into AI and have it draft a cover letter based on them — but including that stuff is essential if you want the letter to actually make you a stronger candidate and not just be a box you’re checking off.
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you need to write a better cover letter
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