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ChatGPT — Your (fast) cover letter consultant

October 24, 2023

You’ve got your résumé looking good. You’ve gone through the cursory “About You” data entry on the web site where that sweet job posting calls to you. And then you see one link to upload the résumé and another to upload a cover letter. Ackk! The thought of sitting at your computer for the rest of the eventing working on that fills you with anxiety and revulsion. But wait! There’s no little red asterisk that indicates a mandatory input. Maybe you should just skip it… Don’t you dare. That often overlooked element can be a game-changer in the job search. If a potential employer has built in the opportunity to submit a cover letter, consider it a gift. Think of it as your personal pitch, the golden ticket that can get your foot in the door.

The cover letter: Worth the Trouble?

Let’s be real: a lot of people dread writing cover letters. Whether it’s the pressure to summarize your life’s work on a single page or the fear of sounding like a broken record, the whole process can feel like a chore. And let’s not forget the ticking clock—between work, family, and that little thing called ‘life,’ who has the time or energy to craft the perfect letter?

Then there’s the anxiety of actually putting pen to paper. Writer’s block, fear of rejection, or even just a lack of confidence in your writing skills can make that cursor on a blank screen seem incredibly intimidating. You may even catch yourself wondering, “What’s the point? I probably won’t get the job anyway.”

And this is exactly where ChatGPT comes in. It’s your go-to partner for creating standout cover letters that can elevate your job search to the next level.

Despite the rise of LinkedIn and other digital shortcuts, many employers still want to see a good ol’ cover letter in that application package. Skipping this step, especially when the job description calls for it, could instantly put you on the ‘nope’ pile. Believe it or not, a cover letter can be the tiebreaker when an employer’s on the fence about you.

An Opportunity to Shine

A cover letter does more than just tick a box; it’s your ace in the hole. It’s your chance to show you’ve done your homework on the company and the role, proving you’re not just spamming resumes into the workosphere. Beyond the stats and accolades on your resume, a well-crafted letter allows you to connect on a more personal level, making you a memorable candidate who stands apart.

Before we dive into the ChatGPT magic, let’s break down the must-haves for any stellar cover letter. Keep in mind, while employers dig a splash of originality, they also have certain expectations you’ll want to meet. Now, let’s unwrap those non-negotiables.

  • Introductory Paragraph: Hook them with why you’re the ideal fit for the job.
  • Tailored Content: Don’t regurgitate your resume. Highlight relevant skills and experiences.
  • Address Job Description: Directly respond to key qualifications or responsibilities listed in the job description.
  • Company Research: Show you’ve done your homework. Reference the company’s culture, mission, or a recent project they’ve worked on.
  • Clear and Concise Writing: No one has time for a novel. Keep it short and sweet.
  • Professional Tone: While a little personality is great, remember this is a job application.
  • Closing Statement: This is your “call to action.” Make it clear what you want to happen next — usually, that’s an interview.
  • Contact Information: Seems obvious, but you’d be surprised how often this gets overlooked.

Meet your new wing-woman in the job-hunting game: ChatGPT. What’s that, you ask? ChatGPT is a language model trained on a vast array of texts, designed to assist you in generating human-like text based on the prompts you feed it. Think of it like having a really well-read buddy who’s ace at wordplay, hanging out in your computer. With ChatGPT, you can beat that blank screen and writer’s block. The best part? It can help you craft a cover letter that’s as unique as you are, while still hitting all those conventional points employers are looking for.

  1. Open the Browser: Head to the ChatGPT website or platform.
  2. Sign Up or Log In: If you’re new, it’s a walk in the park, promise. The default mode (3.5) is just fine for our purposes.
  3. Understanding “Prompts”: Think of them as conversation starters, guiding the model in helping you.
  4. Start a New Chat: Hit that button or link to initiate a new conversation. And hey, don’t be shy—feel free to say “Hi” and engage in a little small talk. Trust me, you won’t weird out the machine.
  5. Craft Your Prompt: Be as specific and descriptive as possible. Something like, Can you help me merge my resume and the job description into a tailored cover letter? works like a charm.
  6. Provide Info: Lay down your resume and the job description, so we can tailor this bad boy perfectly.
  7. Review the Draft: You know you best, so make sure it rings true to you and lines up with the job deets.
  8. Fine-Tuning: Don’t like the first draft? No biggie. Feel free to rephrase your prompt or ask for changes. The sky’s the limit here.
  9. Edit: Tweak it ’til it’s perfect.
  10. Finalize and Send: Save that killer cover letter and get ready to impress.

Résumé and Job Description used to synthesize a Cover Letter

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ChatGPT AI-generated Cover Letter

As you can see, this letter needs a little fine tuning here and there, but is certainly not a bad start!


While the list gives you a roadmap for crafting a killer cover letter with ChatGPT, it’s crucial to dedicate some time to fine-tune what the AI spits out. Even if at first glance the text looks good, remember that you’re the best judge of how well it aligns with both the job requirements and your own personality. So, don’t skip the deep dive.

Double-Check the Chat

Checking that the cover letter doesn’t sound too robotic or generic is key. You might think it’s ironic, asking a machine to help you sound more human, but you’d be surprised how well it can work with the right input from you. Make sure the tone is professional yet personalized, hitting the sweet spot between “[yawn] Oh great — another résumé?” and “Wow, this candidate really gets us.”

The growing integration of Artificial Intelligence into various aspects of life has sparked a fair amount of ethical debates, whether it’s in the classroom, the newsroom, or the boardroom. Concerns often revolve around issues like data privacy, job displacement, and the authenticity of AI-generated content. These ethical considerations shouldn’t be taken lightly.

Creating Paths for Those Who Can Do the Job

But here’s a silver lining: using a tool like ChatGPT could actually level the playing field. Think about it. Some folks might have all the skills needed for a job but struggle when it comes to crafting the perfect cover letter. So, why should they miss out on opportunities just because they’re not Shakespeare when writing isn’t even the main gig? ChatGPT can help bridge that gap, allowing candidates to focus on what really matters for the job at hand.

My own late father, still the most intelligent man I’ve even known, arrived in this country from Puerto Rico at the age of six in the early ’40s. He once joked, sardonically, that school systems put all the non-native English speakers in the back of the classroom with crayons and scrap paper and said, “see you at graduation!” making no real effort to provide immigrant children with anything close to a real education.

He did go on to graduate, join the Air Force, and then walked into a factory job in his early twenties with grit and determination. A savagely hard worker, my father impressed his bosses in every position he held. But as he rose through the ranks at different companies, he had his own secret weapon — his wife. The most brilliant woman I’ve ever known, my mother has always had a gift for language (you can read some of her recent writing right here in The Greylock Glass. Every time my father applied for a new job, the two of them would sit down at the kitchen table to work on his résumé and the cover letter for the position he was aiming for. My father would verbally explain his qualifications and interest in the job, and my mother would bang out the prose on our family’s old manual typewriter. She also lent her skill to the various reports and communications my father was responsible for during his employment. His acumen and attitude, with her writing help, secured positions as lead man and foreman in the early days, and eventually Director of Manufacturing for a multinational corporation. Not an easy feat these days.

While I’m sure my father exaggerated about the crappiness of his education a little, the truth probably wasn’t that far away. No one had even considered the idea of an official English as a Second Language curriculum yet, so some percentage of kids received substandard instruction in any language. Who knows how many non-native English speaking men and women have been denied upward mobility simply because they lacked the writing chops needed to get them the interview where they could really shine. Not everyone is lucky enough to have the help of a spouse or friend who can help them create attention-grabbing letters of interest.

And it’s not like getting help with job application documents is confined to the Blue Collar set. Plenty of executives use consultants to draft their materials, and the internet fairly crawls with people who claim expertise in the area. The résumé is said to have been devised by Leonardo Da Vinci in 1482. Résumé writing services have likely been available to those people who could afford them since 1483.

So, ChatGPT can be a great equalizer, especially for folks whose education didn’t quite provide all the tools needed to draft a polished cover letter from start to finish. Whether English isn’t your native language, or the task simply fills you with dread, this tech can help you focus on showcasing your real qualifications and fit for the role, rather than stressing about the writing itself.

Teachable Moment

To wrap this up, let’s go over what we’ve covered. We took a deep dive into the nuts and bolts of crafting a standout cover letter, looked at how ChatGPT can be your ultimate writing buddy for this task, and discussed the potential ethical dilemma of leaning on AI for a creative boost. Yet, one other benefit to using language generating AI exists: while using AI like this can actually make writing a fun, enjoyable process, it can also be a self-guided tutoring session.

As you work with ChatGPT, you might discover you actually DO have the ideas and creativity to tackle a lot of writing projects. Seeing how it all comes together through this AI tool can serve as a fantastic teaching mechanism, helping you refine your own writing style while saving you precious time.

So go ahead, play around with different prompts and approaches. The more you experiment, the more confident you’ll become, and that will shine through in your cover letter—and your job search. Best of luck out there! Get ready to turn that job hunt stress into some seriously solid results.

Jason Velázquez

Jason Velázquez has worked in print and digital journalism and publishing for two decades.
Phone: (413) 776-5125

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