Writing a Compelling Cover Letter (with AI Tips)
On July 22, 2025, Steve Dalton came back to Pivot with Purpose to share his insights about writing effective cover letters. This event was the third in our Skilled and Ready to Serve: Marketing Your Development Experience Effectively series theme. Nathan Slusher, Georgetown SFS, moderated the discussion.
Cover letters are tricky to write. Yet in today’s dynamic job market, we must be able to draft and adapt our cover letters quickly for new roles and sectors. Given the sheer number of qualified applicants pursuing limited opportunities, making the right impression in our cover letter is critical.
Ineffective cover letters can make us sound either too generic or too eager. We may also fail to use the best keywords or job descriptors to present our expertise most effectively. As we are forced to boil down our (sometimes vast) experiences and strengths into only 300-500 words, the pressure to write the “best” or “ideal” cover letter is immense.
So, where do we even start? Is there an ideal way to discuss our past achievements or experiences? And how can we best present our authentic selves in our cover letter in order to land our dream job?
According to Dalton, it is crucial to write cover letters that are simple in structure and clear in their argument. He also emphasized that our cover letters should answer these two questions:
- Why do you want this job?
- Why are you the best candidate to do it?
Ultimately, the cover letter should offer more insight into our work, skillset, and motivation. Though the resume can highlight our experiences, the cover letter contextualizes them and, perhaps most important, translates our skills into a given company’s needs. In other words, hiring managers will read your resume to see whether you have the background and expertise they desire, but they will look to your cover letter to picture you in that role and gauge your fit within the organization.
In this session, Dalton offered an easy, fill-in-the-blank template to write all our cover letters and to ensure they were effective, persuasive, and answered every question our cover letters are expected to answer: The RAC model.
This model (taken from his book, The Job Closer) instructs us to offer a reason for our candidacy (i.e., the specific skill we possess, or your main point), an anecdote to demonstrate our argument (i.e., a genuine and personal story to illustrate your expertise), and a connection to the hiring company’s work or current initiatives (i.e., how your skills will benefit them).
Using this method, your cover letters will inherently have a simple and clear structure. They will also answer why you want the job (through your reasons) and demonstrate why you are the strongest candidate (by offering an anecdote and connection).
This model also addresses one of the biggest misconceptions many carry subconsciously about what an ideal cover letter looks like. For Dalton, too many cover letters are writer-focused: too long, too over-encompassing, and bereft of any explanation as to how you would benefit the company.
These cover letters are characterized by offering many reasons for your candidacy and, potentially, anecdotes that illustrate your skills. Although your background is important, your resume already accomplishes much of this task.
Instead, we should write reader-focused cover letters that center on the hiring manager’s questions and concerns about us. Again, translating our experience to their needs. Adding this connection between your skills and the job opportunity and offering genuine anecdotes that demonstrate your capabilities allows employers to envision you in the role and understand where you would fit.
Most important, reader-focused cover letters are succinct. No doubt many of us were taught to write cover letters the same way: similar opening lines, exhaustive list of examples to “show” our experience, and a standardized closing paragraph. Hiring managers, however, are sent thousands or more of these letters. As such, being concise in your language is paramount to both stating your case well and standing out.
When writing cover letters, especially those with a simple and repeatable structure, many of us use AI to help with the process. AI tools can help us identify keywords and phrases, outline what we’re missing in our cover letters, and adapt your language to the job posting. Of course, AI also hastens the drafting process, producing language nearly instantaneously.
During his remarks, Dalton acknowledged these advantages and encouraged us to use AI-assisted tools when it made sense to do so. That being said, he cautioned us against relying on it.
AI models have been trained by other users and developers, many of whom (according to Dalton) have learned to compose writer-focused cover letters, rather than those that are reader-focused and, thus, more effective. To phrase it differently: AI-generated cover letters will enumerate reasons for your employment, but they will often struggle to compose genuine anecdotes and fail to connect your skills to the company’s vision and goals.
Though having AI tools immediately on-hand and this easily repeatable method in mind will tempt us to use AI exclusively, we should not do so. Dalton advised attendees to take their time when creating these drafts to ensure that our arguments are authentic and translated for our audience – reading like an AI-prompt is a major red flag for hiring managers.
Undoubtedly, writing cover letters is a daunting process, fraught with misconceptions and pitfalls. Still, Dalton reminded session participants that the basic questions cover letters should answer are relatively simple. Furthermore, he argued that most job postings inevitably attempt to reach candidates who can lead, collaborate, communicate, problem-solve, and get work done effectively and efficiently.
He expanded on this idea by maintaining his belief that all job skills are transferable. Provided we can show our expertise in doing those things well (and carefully addressing how our work will benefit our employer), we will be able to present our qualifications and skills convincingly.
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