By now, most job seekers have at least dabbled with AI when writing a cover letter. And why wouldn’t you? It’s fast, articulate, and never stares blankly at a cursor blinking in an empty text box.

But as they say in Spinal Tap, there’s a fine line between clever and stupid.

If you use it correctly, AI can be a powerful ally in the job hunt. Abuse it, and it will turn on you like Regina George.

AI: Your Cover Letter BFF

  • It gets you unstuck. Writer’s block is bound to happen, whether you haven’t written a cover letter in 12 years or you’re writing your 8th one this week. AI gives you a rough concept to react to, and that can be easier than starting from a blank page.

    Pro tip: when you get stuck, ask AI to give you a list of ideas. If you only ask for one idea, you could get anchored to it (trust me, I’ve done it!). But seeing a list will force you to think through the best one, and might even lead you back to your own idea, which is what often happens to me.

  • It knows the conventions. Structure, length, opening hooks, closing calls to action. AI has absorbed thousands of cover letters and can remind you of what a solid one looks like. It also reminds you to include the basics that some people overlook, like a salutation and sign-off. Strangely formatted cover letters can be a deal-killer, and AI can keep you safe.

    Pro tip: ask AI to provide a general outline for a cover letter before you get started. Or, if you’re wrapping up, ask AI if you missed any basics.

  • It polishes your prose. AI catches what spell-check misses and can smooth out a draft without changing what you mean, including grammar, awkward phrasing, and run-on sentences. And in my opinion, it’s far better than the human eye when it comes to catching the basics.

    Pro tip: don’t forget to gently inform your former editor that his/her services may no longer be needed. My mother, a former English teacher, lamented the other day that I hadn’t asked her to review anything in ages. I had to break the news that she had been replaced by Chatty (my affectionate nickname for ChatGPT).

  • It articulates your accomplishments. If you upload your resume and the job description, AI can help you articulate how your experience and success relate to the job. AI might also help you make connections you hadn’t thought about.

    Pro tip: if you hesitate about tooting your own horn, ask AI to ensure you aren’t missing any selling points. And if you tend to lay on the horn and stop traffic, ask AI to help you tone it down.

AI: Your Mortal Enemy

  • It makes you sound generic. AI defaults to safe, formulaic language. When candidates use it the same way, every cover letter starts to sound the same. And your application might disappear into the pile, along with Average Joe, Cardboard Carly, and Vanilla Vicky.

    The fix: don’t overuse it. The majority of your cover letter should be written by you, not by a Betty Bot.

  • It litters your cover letter with insufferable buzzwords. AI loves obnoxious phrases like dynamic self-starter, cross-functional teams, stakeholder engagement, and thought leadership. Oh, and here’s a classic: “I am writing to express my keen interest in the opening with your organization.” Who says that? A character on BritBox? Come on, Chatty.

    The fix: if AI inserts buzzwords, call her out and ask her not to do it again. AI learns, remember? And make sure your final cover letter doesn’t contain anything remotely resembling a synergistic tiger team.

  • It may (em)dash your chances of getting the job. “I’m eager to join your team—and to gently over-punctuate every thought—because that’s what the robots taught me.”

    A cover letter dripping with em dashes is a dead giveaway that ChatGPT wrote your cover letter.

    The fix: Take out every single em dash. All of ‘em. (See what I did there?)

    And for good measure, call out Chatty and ask her to use them only sparingly, if at all, when she is helping you with writing projects.

  • It hallucinates like it has been to an ayahuasca retreat in Peru. AI knows a lot of stuff, and if it doesn’t, it feels free to make it up.

    The fix: fact-check everything it says, whether it’s about the organization, the role, or even your background.

  • It can’t tell your story. The most compelling cover letters for liberty movement jobs explain why you want this specific role at this specific organization and how your personal story relates. That kind of genuine motivation can’t be code-generated. It has to come from you.

    The fix: don’t let AI write the part about why you want the job and why you believe what you believe. In fact, don’t let AI near it. Katy, bar the door!

    I started reading a cover letter last week, and the first sentence had me hooked. It sounded nothing like the 23 other cover letters I’d read that day, and I couldn’t get enough. It was an engaging personal story that tied beautifully to the job at hand. By the third paragraph, I felt confident I would enjoy having a beer with the author. ChatGPT and Claude might give you a polished letter, but I pinky swear it won’t make the hiring manager want to drink with you.

If you’re curious, I laid out a framework for this article and then asked AI to write the first draft.

She came back with a bland, paint-by-numbers article. I would have fallen asleep reading it had I not been busy counting the NINE em dashes.

Ultimately, I probably spent more time editing and erasing than I would have if I had just started from scratch. That said, she provided a couple of unique ideas I hadn’t considered, and she caught some mistakes in my final draft.

Overall, Chatty proved to be a reliable (if not mildly lame) friend today. And I hope she’s a friend to you next time you write a cover letter!