By Jeff Altman, The Big Game Hunter
EP 3050 In this episode, we’re diving into exactly how to use ChatGPT—not just to write faster, but to write smarter.
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Cover letters, oof, that hurdle we all face, right? They can feel like such a time sink. Oh, definitely. And you’re often left wondering if anyone even reads them properly.
Exactly. But what if there was a way to make it faster? And, you know, maybe even better. Well, that’s kind of what we’re digging into today.
We’re looking at using AI, specifically those large language models everyone’s talking about, to help write cover letters. Okay. And the goal of this deep dive, really, is to give you some solid, actionable prompts that you can actually use, like right away, make the whole thing a bit less painful and hopefully more effective.
Yeah, that sounds good. Because what we found looking into this is, well, the results you get from AI can be all over the place. It can spit out something super basic, almost useless, or with the right guidance, it can actually give you a pretty expert starting point.
That’s the key, isn’t it, the guidance? So let’s start at the beginning. What happens if you just give AI a really simple request? Okay, baseline. Yeah, baseline.
So we looked at an example where someone fed the AI a very basic prompt. Just write a cover letter for a business analyst role at the British Museum. Simple stuff.
Job found on LinkedIn. And what did it turn out? Well, pretty quickly, it generated a standard opening. You know the type.
I’m writing to express my interest. Mentioned having a diverse background. Passion for cultural heritage.
So speed is definitely there. Instant intro paragraph. Instantly.
But, and this is the big but, it was pretty generic. Lacked any real specific details that would make a recruiter sit up and take notice. Right.
It’s like, okay, it looks like a cover letter, but does it say anything? Exactly. Maybe a decent starting point if you’re planning to heavily edit, like a six out of 10 for potential. But not something you’d send as is.
Oh, absolutely not. Maybe a four out of 10 if you just sent that. And here’s where it got interesting.
The skills it mentioned. Ah, okay. What about those? It listed things like data analytics, requirements gathering, process improvement, project management, pretty standard business analyst skills.
Sounds reasonable. It sounds reasonable, but the actual job description for that specific role, it highlighted organizational skills and analytical skills as the top two. The AI just kind of glossed over those specifics.
Huh. So it pulled general skills for the role type, not the skills that specific employer said were most important. Precisely.
You can sort of picture the AI having scanned like thousands of business analysts, job ads, online web scraping, right? So it knows the common keywords, but it doesn’t automatically prioritize what’s in the one job description you care about, which really hammers home that the job description itself has to be your absolute source of truth. Right. That’s the document that matters most.
Absolutely. So that initial test showed, yeah, AI is fast, but a basic prompt gives you a basic, maybe even slightly off target result. That’s often very me-focused.
Here are my general skills rather than here’s how I meet your specific needs. Okay, so the simple approach isn’t quite enough. What’s the next step then? How do you get better results? This is where super specific prompts come in.
That seems to be the crucial difference. Super specific, makes sense. Yeah, because if the AI isn’t naturally zooming in on the job description’s priorities, well, then you have to tell it exactly what to focus on.
You need to guide it much more precisely. Okay, so how do you structure that? What goes into a super specific prompt? Well, we looked at a breakdown for creating what you might call an expert level cover letter. The idea is to structure the prompt around that ideal letter format.
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Tell me more. So for the first paragraph, the hook, you want three key things. First, a really specific compliment about something the organization does.
Not just you’re great, but something concrete. Okay. Second, you draw a parallel between that specific thing and your own worker studies, show you understand their world and how you fit in.
Ah, connecting your value. Exactly. And third, you state your willingness to enhance the top skills they listed in the job description.
This implies you already have those skills, but are ready to apply them there. That’s a much stronger opening. Very targeted.
What about the body paragraphs? Following that model, paragraph two focuses only on the number one skill from their list. Give details, examples. Just the top skill.
Just the top skill. Then paragraph three does the exact same thing, but for the second most important skill they listed. Laser focus.
Totally. And the closing, keep it short, direct. Right.
So you’re basically reverse engineering a great cover letter structure into the AI prompt. You got it. Can you give an example of what that prompt might actually look like, say for that British museum job again? Sure.
So you could try something like this. Act as an expert cover letter writing coach. You have 10 years of experience getting people interviews at top places.
Write a cover letter for the business analyst role at the British museum. Okay, setting the scene. Focus the first paragraph specifically on the British museum’s work and build a parallel to the job’s top rank skills.
Remember, organizational skill was one. Make the paragraphs short and readable. The goal is simple.
Write a letter that gets me an interview. Wow, okay. That’s way more detailed than just write me a letter.
Big difference, right? Yeah. And what happened? What did the AI produce with that level of instruction? Much better. It actually started by mentioning appreciation for the museum and it brought up organizational skills right away in that first paragraph, just like we asked.
Nice. It tried to build that parallel too. Now granted, the AI might put in a placeholder example, so you definitely needed to swap that out with your real experience.
Of course, personalization is still a key. Always. But the paragraph length was good, kept them short.
And it did create separate paragraphs focusing on organizational skills and analytical skills. It followed the structure. So maybe not perfect, didn’t follow every single word.
Literally, perhaps. Not perfectly verbatim, no. But the output was a much stronger starting point.
We’re talking maybe an eight out of 10 for editing now compared to that four out of 10 before. That’s a significant jump. It really shows how moving from a general request to a really specific structured prompt makes a huge difference.
It really does. More targeted input leads to more relevant output. But it’s still important to remember, even with great prompts, it’s a starting point.
Right. Not copy-paste-send. Definitely not.
You still need that human touch, your specific examples, your voice. Okay, so that structured multi-part prompt is one powerful way. Are there other ways to prompt AI effectively? Maybe something a bit simpler.
Yes. There’s another approach that’s a bit more concise up front. The prompt itself is shorter.
Like, write a cover letter with metrics for the following job description. Use my resume for reference and keep it less than 400 words. Okay, simpler prompt.
But you said up front. What’s the catch? The crucial part is what you do next. After you give that initial prompt, you then paste in the important bits of the job description right into the chat.
Ah, okay. You provide the context after the instruction. Exactly.
And then you also paste in your resume, probably best to strip out your home address and phone number first, just for privacy. How do you do that in the chat? Just paste it all in one big block? Usually, you can use Shift plus Enter to create new lines within the chat window. So you can paste the job description, hit Shift plus Enter a couple of times, then paste your resume.
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It keeps it organized for the AI. Got it. So the AI gets the request, the job details, and your background info all at once.
What should you look for in the letter it generates this way? With this method, you’re hoping the AI will pull out your years of experience, maybe some key achievements, ideally with numbers or metrics, if your resume has them. Right, the quantifiable achievements bit from the prompt. Yeah.
It should also clearly reference the specific job title and company. And fundamentally, it needs to connect your skills and the value you bring to that specific role. You’ll probably also see some placeholders, like your name or company address, that you obviously need to fill in.
Makes sense. And I’m guessing the next step is still… Review and personalize, absolutely. No matter which prompt style you use, that step is non-negotiable.
Even if you gave it your resume. Even then. You have to check if the AI represented your experience accurately.
Did it maybe exaggerate something or misunderstand a point? Yeah. And critically, does it sound like you? You need to inject your own voice, your own genuine enthusiasm. That really seems vital.
It can’t just be a list of facts. It needs personality. It needs to connect.
And that actually brings us to another really important perspective shift. A great cover letter isn’t just about you. It’s about the opportunity, about the employer’s needs.
Ah, okay. Less me, me, me and more you, you, you, meaning the company. Kind of, yeah.
It’s about showing you understand their context and how you fit into their goals. So does that mean doing some homework before you even start prompting the AI? Ideally, yes. Yeah.
A little upfront research can make a huge difference. Check out the company’s website, look at their LinkedIn page, maybe see what they’re posting on social media, get a feel for what they’re focused on right now. What kind of questions should you be trying to answer with that research? You want to figure out, okay, what are the absolute must-have requirements for this job based on the description and what I’m seeing? What do I genuinely like or admire about this specific company? Not just any company, but this one.
And maybe reflect on your own motivation. Why this job? Why this company? Why now? So getting clear on those things first, how does that research then translate into using the AI? One really smart strategy is to use your prompt like an outline. Instead of one big instruction, you basically micromanage the AI paragraph by paragraph.
Okay, tell the AI exactly what each section should cover based on your research and the job description. Precisely. You’re guiding it much more closely.
Could you walk us through an example of that, for a different role, maybe video marketing? Sure. You could structure a prompt for a four-paragraph letter like this. Okay, AI, paragraph one.
Start by saying, I’m really enthusiastic about a video marketing specialist role at company name. Mention my five years doing video for ads, social media, digital marketing. And give a specific reason or two why I’m drawn to this company in this role.
Very direct. Then paragraph two. Paragraph two.
Focus on a key strength. Let’s say experience with storyboarding, shooting, editing, optimizing video. Maybe mention I’ve done over 150 videos for corporate clients.
Emphasize an audience-first approach. Maybe hint at a positive result from a past project. Okay, specific skills and proof.
Paragraph three. Paragraph three. This is the why them part.
Explain why I want to work for company name. Mention something specific. I admire maybe their reason campaign, their storytelling style.
Connect my skills to what they seem to value. What do I hope to achieve there? Nice. And the closing.
Paragraph four. Keep it concise. Reiterate my strong interest.
Say I’m eager to discuss it further. And point them to my resume for more details. Standard professional closing.
That feels incredibly structured. You’re really mapping it out for the AI. What kind of draft does that typically produce? You usually get something very well organized.
It’s concise. It’s relevant. It hits all the points you specified.
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But. There’s always a but. There’s always a but.
The language itself might still be a bit, well, AI-ish. A bit generic. Maybe a little stiff.
Right. It follows the structure, but the words might need work. So even with this detailed outline prompt, you still have that polishing step.
Absolutely. And you can even use the AI to help with that part. Oh.
Well, you can ask the AI to critique its own writing. You could prompt it like, looking back at this draft, what are some phrases in here that sound really common? Or maybe even cliche in cover letters? Ah, that’s clever. Get it to identify its own generic bits.
Yeah. And once it points them out, you can say, okay, I want to sound more unique and engaging. Can you suggest some different ways to write those sentences? You can even tell the tone you want.
More conversational. More enthusiastic. Whatever fits.
So you’re using the AI not just to draft, but also to refine and find better phrasing. Exactly. And if you spot a sentence that feels too vague, you can ask the AI for help there too.
This sentence feels a bit weak. Can you give me some tips on how to make it more specific? It might suggest adding numbers, specific examples, or details about your process. It really becomes like a back and forth, like you’re collaborating with the AI to build the final letter.
That’s a great way to put it. It’s an iterative process. Okay, this is super helpful.
We’ve talked about different prompting strategies, providing context, focusing on the employers, or anything else we should cover. Maybe a completely different approach. Well, there is one more strategy worth mentioning, especially for situations where brevity is absolutely key.
It’s kind of the anti-cover letter. Intriguing, tell me more. It’s basically a super short four sentence introduction, maybe five sentences max.
You could use it as the body of an email when you apply, or maybe in those little text boxes in all my application systems. Why so short? The thinking here is all about respecting the recruiter’s time. They get absolutely flooded with applications and emails.
True. So the goal isn’t to tell your whole life story, it’s just to be brief, professional, and intriguing enough to make them click open your resume. That’s the real goal.
Okay, get them to the resume. So what are these magic four sentences? It’s pretty straightforward. Sentence one, state your purpose.
I’m writing to inquire about the opening for the specific job title position. Clear, direct. Got it.
Sentence two. Briefly state your relevant experience and why you think you’re a fit. Something like, I offer X years of experience in your field specialty, and believe this makes me a strong candidate for this opening.
Okay, short and sweet value prop. Sentence three. This one’s clever.
You direct them to the resume for the juicy details. The top portion of my attached resume highlights my career profile, and three key accomplishments that seem particularly relevant to this position. You’re creating a little mystery, making them wanna look.
Ah, I like that. Pointing them to the proof without spelling it all out right there. And the last sentence.
Sentence four. Express interest in talking more, and crucially, mention openness to other roles. I’d welcome the opportunity to speak with you if you feel I’d be a strong candidate for this role, or perhaps another position within your organization.
Why mention other roles? It shows flexibility and broad interest in the company, not just this one specific job. It slightly widens the net, and makes you seem like someone genuinely interested in contributing to their organization. Recruiters often appreciate that.
That four sentence approach is definitely different. Very concise, very focused on just getting that resume viewed. Exactly.
It’s a different tool for a different situation. Perhaps when you know time is incredibly tight. Okay, so we’ve covered a lot from basic AI attempts to super specific prompts, providing context, outlining, refining language, and even this ultra-brief approach.
If we had to boil it down, what are the key takeaways, the best practices for using AI for cover letters? Right, let’s summarize. First, remember, AI is fundamentally a pattern masher. Its first attempt might be generic.
So think of it as a drafter, a template generator, not a final writer. Okay, manage expectations. It’s a starting point.
Definitely. Second, always. Always refine, edit, and personalize.
Check for accuracy, inject your own examples, your own voice. This is critical. You just get the human review.
Never. Third, give the AI context. The job description is essential.
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Your resume is really helpful. The more relevant info it has, the better the starting point will be. Garbage in, garbage out, basically.
Pretty much. Fourth, use specific structured prompts. Whether it’s the detailed hook and skills approach or the paragraph by paragraph outline, guide the AI clearly.
Be the director. Yeah. Fifth, do that little bit of company research beforehand.
Tailor the letter to their needs. Show you understand them. Make it relevant to the reader.
Absolutely. And finally, just make sure it sounds like you. Let your personality come through.
Oh, and one practical tip. Ensure the formatting looks okay. Sometimes AI formatting can be weird, so check it reads well.
Good point. Readability matters. Hugely.
Okay, so the big picture is, AI can be a really powerful assistant for cover letters, a way to beat the blank page and get started faster. But you have to use it smartly. Specific prompts, careful review, and lots of personalization are key.
That’s it, exactly. It’s a tool, not a magic wand. We’ve shared quite a few prompt ideas today, different ways to approach it.
Hopefully you listening can take those, adapt them, and find what works for your own job search. And maybe a final thought to leave you with. Thinking about AI this way, understanding its strengths and its weaknesses, how can that actually make your whole job application process feel more strategic, maybe even more authentic? How so? Well, if AI can handle the initial heavy lifting of drafting, maybe it frees up your mental energy to focus on the parts AI can’t do, like networking, really tailoring your message based on deep research, or prepping thoroughly for interviews.
Right, use the tech to automate the grunt work so you can focus on the high impact human stuff. Exactly. How can these tools help you focus your energy where it matters most? Something to think about.
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