How to Use AI/ChatGPT to Write Your Cover Letter

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AI can be a great tool. Here's how you can leverage AI (specifically ChatGPT) to improve your cover letter.

Photo by Google DeepMind on Unsplash

There's so much discussion about AI, ChatGPT, and how it's changing everything and can be used to solve any problem you have. Perhaps you've wondered if it could help you write your (dreaded) cover letter. You absolutely can. In short, have AI write a cover letter. Then write one that doesn't sound like that at all.

Here's what ChatGPT* gave me for the prompt, "Can you write a cover letter for a software developer manager with diverse experience over 20 years in 100 words?"

Dear Hiring Manager,
I am a Software Developer Manager with over 20 years of diverse experience, and I am excited to apply for the managerial position at your organization. Throughout my career, I have successfully led and mentored teams, delivering high-quality software solutions across various industries. I possess a deep understanding of programming languages, development methodologies, and platforms, allowing me to adapt to different project requirements seamlessly. With a track record of delivering projects on time and within budget, I excel at fostering collaboration and aligning business objectives with technical solutions. I am confident that my expertise makes me an ideal candidate for the Software Developer Manager role at your organization.

Sincerely,
[Your Name]

Sprinkle in some specific technologies, team sizes, & KPIs, fix a bit of grammar, and it's pretty much nailed it. I've read this cover letter hundreds, maybe thousands of times. It's so similar it's almost eerie. But rather than be excited about how much easier this can make life for applicants, I'm fearful for the recruiters and hiring managers that will have to wade through this tidal wave of flavorless text.

I actually don’t dislike everything about this. Structurally it’s fine enough, it has a beginning, middle, and end, and the overall gist seems like what a cover letter is supposed to say. Here's what I think is wrong with the above (other than the details I've already mentioned). Some of this is unfair because it's short and is obviously lacking context full scenario but bear with me:

• It lacks progression.
  A cover letter doesn't need to be your own Moby Dick. However, it should allude to some sort of movement in your career. You learned something as you changed roles and companies and if you're earlier in your career you learned something with each project. Those momentum of those lessons is the important part here, not just repeating the bullet points. What have you done and how does that set you up for what's next? Especially if you're looking for a promotion or other kind of shift, this is your opportunity to set the stage for why you're the right candidate and why the role you're applying for is the obvious next step.

• It doesn't express a goal.
  Think through your reason for applying in the first place. You want the job, or more specifically you want to be considered for the job and get a phone screen or otherwise to the next step. This cover letter doesn't make a case for why this applicant is better than another, why they're a better candidate for the role, the company, or the team. Beyond that it doesn't even say why the applicant wants this role in the first place. It just leaves all of that as implied. Cover letters are your chance to be explicit about both why the role is right for you and you're right for this role. Describe who you are, explain what you’ve done, and say why you’re applying and why this company is the right next step.

• It's redundant.
  There's nothing in this cover letter that you wouldn't already know from the resume. Sure, this is a summary of sorts but even the most cursory resume skim would give the same result. That leaves this cover letter without a real purpose. This might not hurt someone's chances but why waste your time (or that of the reader)?
  
  (This kind of redundancy actually causes a bit of debate in the hiring world, with some taking the overwhelming dominance of bad cover letters to be a reason to not ask for them at all. Instead, I think of cover letters as a massive opportunity and I advise my clients to take this exercise seriously. For my clients that aren't writers, I'll even write it with/for them. If you need help, reach out. )

• It's boring.
  One the big things people don't understand about ChatGPT is that it doesn't actually "know" anything. The (drastically oversimplified) way ChatGPT works is to take all the text in the world and then do incredibly sophisticated pattern matching to spout out a response to a prompt. In this case ChatGPT finds all of the cover letters it's ever seen that fit the mold for a dev manager with 20 years experience and gives what is basically the average of all those things. That's no small feat, but to me this result is at best a starting point. You're not trying be middle of the pack, you're trying to "win." That means a milquetoast cover letter isn't the right tool for the occasion. Resumes leave less room for personality so perhaps AI is better for that task.

Here's my own counter-cover letter, with similar constraints on length and lack of specifics.

Dear Hiring Manager,
The biggest lesson I've learned throughout my career is that you always have time for a mentor. Early in my career that was about more technical topics and getting good at the craft of building building software. Over time it shifted to being about being a better team member and thinking at a higher level about technical decisions. At this point I can lead implementation in multiple languages and platforms, across time zones, industries, disciplines, and team sizes but I'm still ready to learn more.

I'm excited to apply for your open role of Software Developer Manager because so far it seems like the culture is one where I can continue to thrive. The focus on autonomy and promoting from within is incredibly appealing, as I'm ready to learn even more about how my teams, projects, and input can impact the entire company and our customers while still helping others grow in their roles as well. I look forward to hearing from you to learn more about this opportunity.

Sincerely,
[Your Name]

Given the constraints, yes, this is still vague and the learning/mentorship angle isn't going to be universal. Still, consider how much better this frames the assessment of this candidate. They're setting themselves up as a expert but still eager to learn. They want to continue leading but know how they can deepen their expertise. They also have specific reasons for why this role is appealing. This gives the reader a starting understanding of what this candidate is looking for in their next role and they can speak to that in future communication. It's also a true complement to the resume, adding context to how this person's career has progressed. To me that fills in more about this candidate, making them stand out in a sea of blank slates, exactly what you're looking to do.

AI can serve as a great tool to help speed the application process, especially in terms of structure and inspiration. However, don't make the mistake of forgetting that your application needs you in it and AI can't (yet) add that human touch.

* - Grammarly is another AI-powered tool that can help with the writing process.

If you need help with your resume, cover letter, or LinkedIn, a Materials Audit can be just what you need to improve your applications and your confidence.