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July 29, 2025 19 mins

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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

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:01):
The other day, I happened to look at my dashboard
and noticed that a previousepisode number 189, about are
cover letters still importantwas getting a lot of downloads,
and I thought it's probably timeI update that episode.
So here it is.
If you've been thinking aboutusing ChatGPT or another AI tool

(00:23):
to help you write your coverletter, you're not alone In this
job market, where time is tightand the pressure to stand out
is high.
Many mid-career professionalsare wondering if using ChatGPT
or AI to write their coverletter is a smart shortcut or a
risky move.
In this episode, I'll unpackfor you five key things you need

(00:47):
to know before letting AI writeyour next cover letter.
I'll talk with you about how touse AI the right way, what
hiring managers are reallylooking for and why your unique
voice still matters more thanever.
So, whether you're actively jobsearching or just curious about
the role AI may play in yourcareer journey, this episode

(01:11):
will help you build a smarter,more authentic application
strategy without losing thepersonal touch that makes you
stand out.
So let's get started.
Hello, my friends, this is theMid-Career GPS Podcast, and I'm

(01:36):
your host, jon Nerrell.
I help mid-career professionalslike you find a career they
love or love the one they have,using my proven four-step
formula.
Before we get started, I've gotsomething free I want to give
you If you're frustrated withwhere your job search is going.
I created a free guide alongwith a 20-minute companion video

(01:59):
called why your Mid-Career JobSearch Isn't Working and what to
Do About it.
I want to give a shout out toone 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 strategyand made the process feel more

(02:19):
focused and manageable.
Most importantly, it shifted mymindset from frustration to
clarity.
End quote.
So if you want to get this freeguide and video why your
mid-career job search isn'tworking and what to do about it
all you have to do is go to mywebsite, check out
johnnerrellcom, forward slashresources or you can check the

(02:40):
show notes to get your freeguide and the video training.
You can check the show notes toget your free guide and the
video training.
Okay, this question aboutwhether or not I should use AI
to write my cover letter or helpme in my job search am I
cheating?
Is it worth it?
There's a lot of things for usto unpack here.
But I want to offer you rightoff the bat tip number one AI

(03:05):
can be a great starting pointfor your cover letter, but it is
not, nor should it ever be, thefinal draft.
So look, cover letters have aplace in this job market.
What I offer to my clients isthat if the job application says
to submit a cover letter, youdo.

(03:26):
If it says it is optional andthere is a place for you to
upload your cover letter, youshould.
If there is no mention of acover letter and it says it is
not mentioned anywhere, don'tGiving them more information
than what they're asking for mayactually be a detriment.

(03:48):
So when you get an opportunityto write that cover letter and
expand about a particular skillset, experience or achievement
that you have and really let thehiring manager in on why you
believe you're the best personfor the job, giving an AI tool

(04:10):
like ChatGPT something to workfrom can provide a solid
structure, format and phrasingto get you started with that
cover letter.
But there's a pitfall here.
Hiring managers and recruitersare getting more savvy in terms
of spotting when there is, let'sjust say, an overly polished or

(04:35):
overly AI-generated coverletter, that may come across as
being inauthentic.
If that cover letter you'resubmitting doesn't sound like
you wrote it it is about yourstory, your impact and sounds
like it is in your voice, youshouldn't submit it.

(04:55):
Okay, because imagine gettingcalled in for that interview and
now they've read your coverletter and they're expecting you
to sound one way and you comein completely different.
We don't want to raise a redflag like that.
So make sure that the coverletter is reflective of who you
are in your voice.
Okay, I often like to say thatcover letter should be a

(05:21):
document that represents yourexperience.
Okay, it would be like lookinginto a mirror and getting to see
exactly who you are.
If it's overly polished, overlygeneral, it's filled with a
bunch of word salad, it's notthe right cover letter.
Don't submit it.
Okay.
And that leads me to tip numbertwo Customizing your cover

(05:47):
letter is essential.
Do not overlook this step.
So you can use tools likeGrammarly or AI may have a
grammar component in there tohelp clean up some of your
language.
Certainly, word and Google Docshas a spell checker in there as
well, but you want to make sure, when you are writing this

(06:11):
cover letter, that, when itcomes to customizing that cover
letter, you are speakingspecifically to the role, the
company, their problems, theirchallenges and how you are the
person to help them solve thatparticular problem.

(06:31):
Depending upon how muchinformation you're giving say,
chat GPT to help you constructthe cover letter it may fall
short without the appropriateprompts to actually give you a
cover letter that is reflectiveof who you are and how your

(06:52):
experiences connect to that ofthe companies.
More than ever, especially atmid-career I've said this before
your results matter.
So your ability to demonstrateand communicate how what you've
accomplished aligns with thecompany's strategic goals and

(07:13):
missions is critical.
Okay, so, as a mid-careerprofessional, you need to show
up and not do so in a way, let'ssay, as an entry-level
professional or someone who isjust fresh out of college.
This isn't about creating alaundry list of things that
you've done.
Why should they care?
Why does it matter to them?

(07:34):
Why should they believe you'rethe right person for the job?
This is where, in the coverletter, you get to show your
strategic alignment to theposition 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 bitlately too right.
So it is the ethical andtransparency question about

(07:58):
whether you should divulgewhether or not you had AI help
you write your cover letter.
So, keep in mind, it's notrequired, okay, it's not
required that you divulge it,but what is the story you want
to tell?
What is the story you want tocommunicate about how you are
current with certain skills andyou know how to use certain

(08:22):
tools to make it easier for you.
Look, we're at a time right nowwhere I couldn't imagine anyone
saying, oh, you know when I,when I wrote that cover letter,

(08:43):
um, I, uh, uh, I, um, I used thesoftware program called word
and, um, oh, it was great.
It formatted everything andmade it all nice and polished
and stuff, and and I'm someonewho really enjoys using a manual
typewriter to type out my coverletters, 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 lookedat like you had three heads,
okay, so we use tools to makeourselves more productive, more

(09:08):
efficient, to make things easy,right?
So just because we can use AIor chat GPT, should we use it
without disclosing it?
Or is it a talking point foryou in terms of your skill set
and how current you are to sayin this interview look, we know

(09:32):
AI is emerging very quickly and,as I've been learning how to
use AI full transparency here'show I used it to help me write
my cover letter.
But here's why I just didn'tgive you what it spit out.
That's for you to decide howyou want to play that, but I
would offer you that talkingabout how you're growing your

(09:54):
skills is always a good thing.
All right.
Tip number four AI does notreplace self-reflection or
clarity.
In other words, as one of mydear coach colleagues, susan,
says to me, ai cannot give youthe aha.

(10:16):
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 yousomething it thinks is going to
align with what you've told itto do.
You have to read that anddecide.

(10:36):
What truly matters to you Issomething that is phrased a
certain way, not as impactful asyou would like it.
Right?
A cover letter needs to be aclean and clear document about
who you are, what you do and whyyour accomplishments should be
of a matter to the hiringmanager or the interview team,

(11:01):
about why why you are the bestfit for the job.
Okay, so when you download thatfree guide that I told you
about at the top of the episode,there is an opportunity within
that free guide why yourmid-career job search isn't

(11:23):
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 4FFramework essentially is your
promotion blueprint to eithergetting that next advancement
opportunity or getting that nextposition.
It starts with being clearabout what it is that you want,

(11:48):
and it's not just about oh, I'man 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 youtell.
So, having that career clarityto firmly and fully communicate

(12:10):
why you're the best person forthe job, that can come out in a
cover letter, and then you getto the interview and it comes
out even more when you aretalking about why you believe
this is a great fit for you inthis role.
By the way, fit is the first Fin the framework.
Okay, right.

(12:32):
So when you are thinking aboutwriting this cover letter,
here's what I want you toconsider Take some time to think
about what truly matters foryou 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 ita cover letter.

(12:53):
Please, please, please, do notjust upload your resume and your
resume and the job posting andsay, hey, can you write me a
cover letter on this?
It's not going to give you whatyou really want.
You've got to get a context andbackground and experiences and
what's important to you, and soI 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

(13:16):
, so it gives you exactly whatit is that you want.
So just to recap a little bit,okay.
So the first tip was AI is agreat starting point.
It's never going to be thefinal draft.
Two is about customizing isabsolutely essential, right?
So you want to make sure youcustomize and tailor that letter

(13:37):
to the role and the company andwhy you're the best fit for it.
We talked about whether or notyou should divulge, whether or
not you've used AI as a tool tohelp you write it, and certainly
AI is not going to replace yourown career clarity.
It cannot give you the aha thatyou want.
But if there's one tip I wantyou to consider here, it's this

(13:58):
one.
So lean into this one a littlebit.
Okay, using AI be it ChatGPT oranother tool using AI can
absolutely level the playingfield for you as you're applying
for positions.

(14:18):
If and if is in big capitalletters, my friends if it is
used strategically, if you aresomeone who is confident in your
work and ability, but you maynot be the best writer, ai can

(14:42):
absolutely level the playingfield for you by giving you a
stronger written voice.
Ai may be able to phrase thingsin ways you hadn't considered.
Okay, so, like any tool, it isabout how you use it, so it

(15:05):
isn't just taking the firstthing that comes out.
There's going to be somerevisions, some tweaking, some
enhancements, some changes, andone of the things I love
specifically about using ChatGPTis that in that thread, for
whatever chat you have started,it's like a working document
that keeps getting bigger andbigger and bigger.

(15:27):
Okay, so here's what I want youto think about, especially if
you're having any reservationsaround this what is the
difference between using AI tohelp you amplify your voice
versus letting it speak for you?
Imagine taking that questioninto an interview, that you take

(15:54):
that in and say look, I'mlearning how to use AI and I'm
using it as a way to help meamplify 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 reallyeffective.
Here's why the cover letter Isubmitted for this role was
different for the one Isubmitted for your competitor,

(16:18):
and you and I are now talkinghow do I help you?
How do we see if this is agreat fit?
I think it is time that weunderstand where AI gets
compartmentalized for us in ourwork okay and we think about

(16:39):
where we can leverage it, how wecan let it help us okay, what
might that actually look like?
And then figure out what youwant to do with it, okay.
So cover letters yeah, they'restill important when they are

(16:59):
asked for, when they arerequired, and it gives you an
opportunity to tell your storyfrom that place of value and
service.
I am a firm believer.
If you have an opportunity toshare more information with an
HR representative or hiringmanager prior to the interview
about why you believe you are agreat fit for a particular role,

(17:20):
that is absolutely where astrategic cover letter can help
you Absolutely, and if you use atool like AI to help you do it,
you get the final say onexactly what that looks like to
make sure you are representingyourself as the best possible

(17:41):
candidate you can.
All right, my friends hope thiswas helpful.
If you enjoyed this, please dome a favor and share it with
someone you know.
Go to my website,johnnerrellcom.
Forward slash resources tocheck out that new guide and
video.
And until next time, rememberthis you will build your
mid-career GPS one mile or onestep at a time and, more

(18:03):
importantly than ever, how youshow up matters.
Make it a great rest of yourday.
Thank you for listening to theMid-Career GPS podcast.
Make sure to follow on yourfavorite listening platform and,
if you have a moment, I'd loveto hear your comments on Apple

(18:23):
Podcasts.
Visit JohnNarrowcom for moreinformation about how I can help
you build your mid-career GPSor how I can help you and your
organization with your nextworkshop or public speaking
event.
Don't forget to connect with meon LinkedIn and follow me on
social at John Darrell Coaching.
I look forward to being backwith you next week.
Until then, take care andremember how we show up matters.

(18:46):
Thank you.
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