307: Should You Use AI to Write Your Cover Letter? 5 Tips to Help You Decide

Ever wondered if ChatGPT, or any AI tool, could just write your cover letter for you? You’re not alone. With today’s competitive job market and the pressure to stand out, many mid-career professionals are turning to AI to help speed up their application process. But here’s the truth: while AI can be a helpful tool, it’s not a shortcut to getting hired.

In this episode of The Mid-Career GPS Podcast, John Neral explores five essential strategies to help you use AI effectively without losing your voice. You’ll learn when cover letters still matter, how to use AI to support (not replace) your message, and why authenticity is still the most powerful factor in your job search.

If you're a mid-career professional in your 30s, 40s, or 50s who feels stuck, undervalued, or uncertain about your next step, this episode offers guidance, clarity, and actionable tips to help you move forward.

WHAT YOU’LL LEARN IN THIS EPISODE:

• When cover letters are still expected and why they matter
• How AI can support your writing, but not be the final voice
• Why overly polished, generic letters can harm your chances
• The difference between amplifying your voice vs. outsourcing it
• How to use AI ethically and transparently in the job search process
• Why self-reflection is still key to creating an effective application

MENTIONED IN THIS EPISODE:
🎯 FREE GUIDE + VIDEO: "Why Your Mid-Career Job Search Isn’t Working (and What to Do About It)"
Get your step-by-step guide and 20-minute video to help you build a smarter, more strategic job search. Visit johnneral.com/resources to download it today.

IDEAL FOR:
Mid-career professionals, ages 35–55, who are navigating a challenging job search, exploring new opportunities, or struggling to articulate their value in a competitive market.

KEYWORDS FOR SEO:
AI cover letter writing, ChatGPT job search, mid-career job seekers, cover letter tips, job application help, career clarity, authentic job search, resume and cover letter, using AI for job search, writing help for professionals

Chapters

• 0:00 Are Cover Letters Still Important?
• 2:42 AI as a Starting Point
• 5:41 Why Customization Is Essential
• 7:54 The Ethics of Using AI
• 10:08 AI Cannot Replace Self-Reflection
• 14:18 Leveling the Playing Field
• 17:07 Final Thoughts and Call to Action

Transcript

Speaker 1: 0:01

The other day, I happened to look at my dashboard and noticed that a previous episode number 189, about are cover letters still important was getting a lot of downloads, and I thought it's probably time I update that episode. So here it is. If you've been thinking about using ChatGPT or another AI tool to help you write your cover letter, you're not alone In this job market, where time is tight and the pressure to stand out is high. Many mid-career professionals are wondering if using ChatGPT or AI to write their cover letter is a smart shortcut or a risky move. In this episode, I'll unpack for you five key things you need to know before letting AI write your next cover letter. I'll talk with you about how to use AI the right way, what hiring managers are really looking for and why your unique voice still matters more than ever. So, whether you're actively job searching or just curious about the role AI may play in your career journey, this episode will help you build a smarter, more authentic application strategy without losing the personal touch that makes you stand out. So let's get started. Hello, my friends, this is the Mid-Career GPS Podcast, and I'm your host, jon Nerrell. I help mid-career professionals like you find a career they love or love the one they have, using my proven four-step formula. Before we get started, I've got something free I want to give you If you're frustrated with where your job search is going. I created a free guide along with a 20-minute companion video called why your Mid-Career Job Search Isn't Working and what to Do About it. I want to give a shout out to one of my listeners, naira, who downloaded the free guide. She offered this testimonial. She said, quote the clear, practical four-step framework helped me rethink my strategy and made the process feel more focused and manageable. Most importantly, it shifted my mindset from frustration to clarity. End quote. So if you want to get this free guide and video why your mid-career job search isn't working and what to do about it all you have to do is go to my website, check out johnnerrellcom, forward slash resources or you can check the show notes to get your free guide and the video training. You can check the show notes to get your free guide and the video training.

Speaker 1: 2:51

Okay, this question about whether or not I should use AI to write my cover letter or help me in my job search am I cheating? Is it worth it? There's a lot of things for us to unpack here. But I want to offer you right off the bat tip number one AI can be a great starting point for your cover letter, but it is not, nor should it ever be, the final draft. So look, cover letters have a place in this job market.

Speaker 1: 3:20

What I offer to my clients is that if the job application says to submit a cover letter, you do. If it says it is optional and there is a place for you to upload your cover letter, you should. If there is no mention of a cover letter and it says it is not mentioned anywhere, don't Giving them more information than what they're asking for may actually be a detriment. So when you get an opportunity to write that cover letter and expand about a particular skill set, experience or achievement that you have and really let the hiring manager in on why you believe you're the best person for the job, giving an AI tool like ChatGPT something to work from can provide a solid structure, format and phrasing to get you started with that cover letter. But there's a pitfall here. Hiring managers and recruiters are getting more savvy in terms of spotting when there is, let's just say, an overly polished or overly AI-generated cover letter, that may come across as being inauthentic. If that cover letter you're submitting doesn't sound like you wrote it it is about your story, your impact and sounds like it is in your voice, you shouldn't submit it. Okay, because imagine getting called in for that interview and now they've read your cover letter and they're expecting you to sound one way and you come in completely different. We don't want to raise a red flag like that. So make sure that the cover letter is reflective of who you are in your voice. Okay, I often like to say that cover letter should be a document that represents your experience. Okay, it would be like looking into a mirror and getting to see exactly who you are. If it's overly polished, overly general, it's filled with a bunch of word salad, it's not the right cover letter. Don't submit it. Okay. And that leads me to tip number two Customizing your cover letter is essential.

Speaker 1: 5:49

Do not overlook this step. So you can use tools like Grammarly or AI may have a grammar component in there to help clean up some of your language. Certainly, word and Google Docs has a spell checker in there as well, but you want to make sure, when you are writing this cover letter, that, when it comes to customizing that cover letter, you are speaking specifically to the role, the company, their problems, their challenges and how you are the person to help them solve that particular problem. Depending upon how much information you're giving say, chat GPT to help you construct the cover letter it may fall short without the appropriate prompts to actually give you a cover letter that is reflective of who you are and how your experiences connect to that of the companies. More than ever, especially at mid-career I've said this before your results matter. So your ability to demonstrate and communicate how what you've accomplished aligns with the company's strategic goals and missions is critical.

Speaker 1: 7:16

Okay, so, as a mid-career professional, you need to show up and not do so in a way, let's say, as an entry-level professional or someone who is just fresh out of college. This isn't about creating a laundry list of things that you've done. Why should they care? Why does it matter to them? Why should they believe you're the right person for the job? This is where, in the cover letter, you get to show your strategic alignment to the position and not just what you've done. So this next tip comes up a lot, and I will tell you I have coached on this quite a bit lately too right.

Speaker 1: 7:54

So it is the ethical and transparency question about whether you should divulge whether or not you had AI help you write your cover letter. So, keep in mind, it's not required, okay, it's not required that you divulge it, but what is the story you want to tell? What is the story you want to communicate about how you are current with certain skills and you know how to use certain tools to make it easier for you. Look, we're at a time right now where I couldn't imagine anyone saying, oh, you know when I, when I wrote that cover letter, um, I, uh, uh, I, um, I used the software program called word and, um, oh, it was great. It formatted everything and made it all nice and polished and stuff, and and I'm someone who really enjoys using a manual typewriter to type out my cover letters, but this just made it easier. No, no one's saying that, right, in fact, if you were to say that, you'd probably be looked at like you had three heads, okay, so we use tools to make ourselves more productive, more efficient, to make things easy, right? So just because we can use AI or chat GPT, should we use it without disclosing it? Or is it a talking point for you in terms of your skill set and how current you are to say in this interview look, we know AI is emerging very quickly and, as I've been learning how to use AI full transparency here's how I used it to help me write my cover letter. But here's why I just didn't give you what it spit out. That's for you to decide how you want to play that, but I would offer you that talking about how you're growing your skills is always a good thing. All right.

Speaker 1: 9:57

Tip number four AI does not replace self-reflection or clarity. In other words, as one of my dear coach colleagues, susan, says to me, ai cannot give you the aha. Your coach colleague, susan, says to me AI cannot give you the aha Right. So what do we mean by that? Ai is going to give you something it thinks is going to align with what you've told it to do. You have to read that and decide. What truly matters to you Is something that is phrased a certain way, not as impactful as you would like it. Right?

Speaker 1: 10:41

A cover letter needs to be a clean and clear document about who you are, what you do and why your accomplishments should be of a matter to the hiring manager or the interview team, about why why you are the best fit for the job. Okay, so when you download that free guide that I told you about at the top of the episode, there is an opportunity within that free guide why your mid-career job search isn't working and what to do about it. To get a masterclass. Now, it's a paid masterclass, it's $37, but it is called the 4F Framework, and the 4F Framework essentially is your promotion blueprint to either getting that next advancement opportunity or getting that next position. It starts with being clear about what it is that you want, and it's not just about oh, I'm an outstanding project manager, I want to do project management. It goes much deeper than that, because your fit and why that's needed is part of the story you tell. So, having that career clarity to firmly and fully communicate why you're the best person for the job, that can come out in a cover letter, and then you get to the interview and it comes out even more when you are talking about why you believe this is a great fit for you in this role. By the way, fit is the first F in the framework. Okay, right.

Speaker 1: 12:32

So when you are thinking about writing this cover letter, here's what I want you to consider Take some time to think about what truly matters for you and what you want to communicate in this cover letter. You're going to feed ChatGPT, for example, as much information as you possibly can to write it a cover letter. Please, please, please, do not just upload your resume and your resume and the job posting and say, hey, can you write me a cover letter on this? It's not going to give you what you really want. You've got to get a context and background and experiences and what's important to you, and so I just kind of like to say it's like feeding a monster. Right, it's a friendly monster, but you got to feed the monster, so it gives you exactly what it is that you want. So just to recap a little bit, okay.

Speaker 1: 13:24

So the first tip was AI is a great starting point. It's never going to be the final draft. Two is about customizing is absolutely essential, right? So you want to make sure you customize and tailor that letter to the role and the company and why you're the best fit for it. We talked about whether or not you should divulge, whether or not you've used AI as a tool to help you write it, and certainly AI is not going to replace your own career clarity. It cannot give you the aha that you want. But if there's one tip I want you to consider here, it's this one. So lean into this one a little bit.

Speaker 1: 14:02

Okay, using AI be it ChatGPT or another tool using AI can absolutely level the playing field for you as you're applying for positions. If and if is in big capital letters, my friends if it is used strategically, if you are someone who is confident in your work and ability, but you may not be the best writer, ai can absolutely level the playing field for you by giving you a stronger written voice. Ai may be able to phrase things in ways you hadn't considered. Okay, so, like any tool, it is about how you use it, so it isn't just taking the first thing that comes out. There's going to be some revisions, some tweaking, some enhancements, some changes, and one of the things I love specifically about using ChatGPT is that in that thread, for whatever chat you have started, it's like a working document that keeps getting bigger and bigger and bigger.

Speaker 1: 15:27

Okay, so here's what I want you to think about, especially if you're having any reservations around this what is the difference between using AI to help you amplify your voice versus letting it speak for you? Imagine taking that question into an interview, that you take that in and say look, I'm learning how to use AI and I'm using it as a way to help me amplify my voice, rather than letting it speak for me. Here's what I'm learning, here's what I'm doing, here's where I'm seeing it be really effective. Here's why the cover letter I submitted for this role was different for the one I submitted for your competitor, and you and I are now talking how do I help you? How do we see if this is a great fit? I think it is time that we understand where AI gets compartmentalized for us in our work okay and we think about where we can leverage it, how we can let it help us okay, what might that actually look like? And then figure out what you want to do with it, okay. So cover letters yeah, they're still important when they are asked for, when they are required, and it gives you an opportunity to tell your story from that place of value and service. I am a firm believer. If you have an opportunity to share more information with an HR representative or hiring manager prior to the interview about why you believe you are a great fit for a particular role, that is absolutely where a strategic cover letter can help you Absolutely, and if you use a tool like AI to help you do it, you get the final say on exactly what that looks like to make sure you are representing yourself as the best possible candidate you can.

Speaker 1: 17:43

All right, my friends hope this was helpful. If you enjoyed this, please do me a favor and share it with someone you know. Go to my website, johnnerrellcom. Forward slash resources to check out that new guide and video. And until next time, remember this you will build your mid-career GPS one mile or one step at a time and, more importantly than ever, how you show up matters. Make it a great rest of your day. Thank you for listening to the Mid-Career GPS podcast. Make sure to follow on your favorite listening platform and, if you have a moment, I'd love to hear your comments on Apple Podcasts. Visit JohnNarrowcom for more information about how I can help you build your mid-career GPS or how I can help you and your organization with your next workshop or public speaking event. Don't forget to connect with me on LinkedIn and follow me on social at John Darrell Coaching. I look forward to being back with you next week. Until then, take care and remember how we show up matters. Thank you.