Why NOT use ChatGPT to write your cover letters

Yes, I know that many candidates and recruiters share an aversion to cover letters. If you're on their camp, refusing to write (or read) them, I'm afraid this article is not for you.

On the other hand, if you're struggling with a job search, and on the fence about the usefulness of cover letters, read on.

Why care about your cover letters?

Ask A Manager is a big proponent of cover letters:

Your cover letter is where you make a case for why you’d excel at the job, aside from what’s in your resume. A good cover letter can be the thing that gets you an interview.

As someone in a hiring position who had to sift through dozens of shortlisted resumes that all looked the same, I wholeheartedly agree that a good cover letter can make your application stand out.

But who has the time to write compelling cover letters for all their applications?

The main excuse I hear from people using conversational AI to write their cover letters is, "I'm trying to maximize time and apply for as many roles as possible."

This argument only makes sense if this "high volume" approach is yielding a good application/interview rate for you.

I always tell my mentees that, early in my career, when I was ready to move on to my next job, I'd spend hours searching for lesser-known companies I'd be excited to work for. Then I'd apply with customized cover letters that described my enthusiasm about the role and how I thought my work experience qualified me for the job. My process would typically yield five applications or so, followed by interviews with maybe three or four companies, and finally a couple of offers from which to choose from.

Granted, this all happened 20+ years ago, after automated filtering became a thing, but before AI chatbots started screening candidates. But if you're among the vast group of job seekers complaining about not getting any interviews after sending hundreds of applications, it would make sense to at least try my approach for a short period.

What I'm suggesting doesn't necessarily requires investing more time on your search efforts. If you're unable or unwilling to carve out additional time for job hunting, changing how you're allocating the available time might be enough to start getting better results.

(Treat it as an experiment to help you find the right repeatable process that gets you the desired results. If you see positive results, you won't be the first, and I hope you'll write me like others did in the past to share the good news when they accepted a job offer.)

What is so bad about using ChatGPT to write your cover letters?

Let me use an example about fiction writing to illustrate the issue.

"Write a thousand-word short story in the style of Curtis Sittenfeld that includes these elements: lust, kissing, flip-flops, regret and middle age."

This was the prompt used in a creative writing contest between novelist Curtis Sittenfeld and ChatGPT, which was trained with 5 of Sittenfeld's books.

You can listen to a conversation with the author that includes excerpts from both written submissions, or read about the experiment (paywalled article from The New York Times).

I don't think the verdict will surprise anyone here. ChatGPT is the clear winner in speed ("a million times faster"), but it generated a "dull and soulless" short story that, albeit "smoothly written", was drastically inferior to the novelist's.

While a cover letter is obviously not the same as fiction writing, it's easy to see the parallels here. Go look at the examples of good cover letters found in the Ask A Manager link provided at the top. Then try to get ChatGPT to write one that doesn't sound bland and generic in comparison, or doesn't use the same lines as other candidates using ChatGPT would use. Do you want to sound exactly like your competition? Or spend significant amounts of time trying to prompt AI to sound less boring and more like you? I didn't think so.

There are plenty of good uses for ChatGPT in your application materials...

An AI-powered writing assistant can be a powerful tool when you're writing a job application. It's not a bad idea to ask it to proofread a paragraph, or offer suggestions to make your point more concisely, or critique your writing to see if it can provide useful ideas or phrasing.

Seth Godin offers some great tips on how to use custom instructions to put ChatGPT to work for you. (He references the useful article Using ChatGPT Custom Instructions for Fun and Profit by Dan Shipper.)

... but writing cover letters for you is probably not one of them

Looking for a new job can be exhausting and stressful. It's tempting to try and make this process more efficient by asking a generative AI tool to write cover letters for you.

Still, unless you're the rare exception who figured out how to effectively delegate to AI the critical task of conveying your enthusiasm for a job and why you'd be particularly good at it, you're better off writing your application materials yourself.

If you've already built a notable portfolio that's not entirely based on coursework assignments, avoiding the bland and soulless prose plaguing 95% of the cover letters out there could be all that's missing to take your job search to a whole new level.