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Writer's pictureAndrew Quagliata

Demystifying Cover Letters with My AI-Powered Cover Letter Coaching Tool

Between my professional experience as a hiring manager and academic experience teaching business writing at the university-level, I’ve read thousands of cover letters. Every search committee I sit on, and every semester when I read my student’s cover letters, I draw the same conclusion: job applicants do not seem to understand what to write to potential employers. 


After reading dozens of books and articles written by career experts about cover letters, I’ve found that advice differs widely, so it’s not surprising that job applicants are confused. 


This article walks you through the four different buckets I place cover letters in, helps you understand the purpose of a cover letter from the employer’s perspective, and shares details about (and a link to) an artificial intelligence cover letter coaching tool I developed that follows the best practices I teach my students and use with my clients.


What bucket does your cover letter end up in?


When I review cover letters, I usually can place them into one of four buckets pretty quickly.


Bucket 1: The applicant is objectively not qualified. The individual doesn’t meet the minimum requirements for the position. In these situations, I assume the applicant didn’t read the job posting and they are immediately disqualified. Bucket 1 is also known as the trash bucket.


Bucket 2: The applicant disqualifies themself. The individual demonstrates they do not meet the basic writing proficiency required for the job, or worse, the letter includes an error that reflects poor attention to detail (e.g., a reference to a different job they are applying for). Perfect communication isn’t always necessary in workplace communication, but your cover letter should present your best work. Consider Bucket 2 the recycling bucket.


Bucket 3: The applicant doesn’t present themself well. The letter may be well-written, but it often has a one-size-fit all quality: the applicant focuses on the past without explaining why they would be a good fit for the specific position. These applicants go into the maybe bucket


Bucket 4: The applicant demonstrates how their experience has prepared them for the position they are applying for. The high-quality writing shows they have closely read the job posting, they understand the organization’s needs, and they address how they can meet those needs. These applicants go into the Let’s get them on the phone bucket


Most letters fall into Buckets 2 and 3. If you understand the purpose of cover letters, you can greatly increase your chances of ending up in Bucket 4. 



What’s the purpose of a cover letter?


Let’s explore the purpose of a cover letter from the employer’s and applicant’s perspective.


Employer’s Perspective

Employers use cover letters as a screening tool. More and more, employers use applicant tracking systems to scan cover letters for keywords, and a human won’t see your letter unless there’s a match. That’s why the one-size-fits-all approach is risky.


Employers may use cover letters to assess your communication skills, writing ability, and/or ability to persuade. 


If a cover letter is required and you don’t submit one, you run the risk of being disqualified for not following directions. It’s a sign you might not follow directions on the job. 


If a cover letter is optional, and you submit a resume without a cover letter, some employers may use this to gauge whether you “go the extra mile” or “do the bare minimum.” 


Applicant’s Perspective

The purpose of a cover letter isn’t to get a job. The highest-level purpose of a cover letter is to obtain an interview. Many applicants - often those with impressive work experience - may tend to put too much information in their cover letters and often mistakenly try to include the same information that can be found in their resumes. Don’t make your cover letter try to do something it isn’t designed to do. 


How can you use AI to help you draft a cover letter?

Writing a cover letter is like playing golf - most applicants hit their balls into the rough, but using Dr. Q’s Cover Letter Coach should help keep you on the fairway (i.e., place your application in Bucket 4).


Using OpenAI’s ChatGPT, I’ve programmed the tool to walk you through the cover letter writing process. I will continue to develop it to help users overcome many of the mistakes I’ve seen in the thousands of cover letters I read in the last 20 years. 


My approach to building this tool is informed by real-world experience as a hiring manager and my academic training in communication, which is deeply rooted in rhetorical principles and an understanding of how busy adults read. The AI tool is pretty good, but it doesn’t always get it right, so you should always review the outputs carefully to ensure they accurately reflect your experiences and qualifications.


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I invite you to experiment with Dr. Q's Cover Letter Coach. This tool, built on the foundation of best practices I teach in my classes and share with my clients, is designed to help you avoid common pitfalls and position your application into the let's get them on the phone bucket. I would be delighted to hear about your experience using the tool and wish you the best in your job search.

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