Pod Insights No B.S. Job Search Advice Radio Use ChatGPT to Write a Killer Cover Letter About this episode EP 3050 In this episode, we’re diving into exactly how to use ChatGPT—not just to write faster, but to write smarter. ABOUT JEFF ALTMAN, THE BIG GAME HUNTERPeople hire Jeff Altman, The Big Game Hunter to provide No BS job search coaching and career advice globally because he makes job search and succeeding in your career easier. Schedule a discovery call to speak with me about one-on-one or group coaching during your job search at www. TheBigGameHunter.us. You will also find great info and job search coaching to help with your job search at JobSearch. Community You can get free copies of 25 Interview Questions and Answers, How to Craft a Compelling Elevator Pitch in 20 Seconds or Less, Get Ready for the Job Jungle, Diagnosing Your Job Search Problems, No BS Resume Advice, and Prove Your Worth First, Then Negotiate. Receive free weekly suggestions and more. Subscribe to No BS Job Search Advice Radio, the #1 podcast in Apple Podcasts for job search with more than 3000 episodes. Connect on LinkedIn: https://www.linkedin.com/in/TheBigGameHunter We grant permission for this post and others to be used on your website as long as a backlink is included to www. TheBigGameHunter.us and notice is provided that it is provided by Jeff Altman, The Big Game Hunter as an author or creator. Not acknowledging his work or providing a backlink to www. TheBigGameHunter.us makes you subject to a $1000 penalty which you proactively agree to pay. Please contact us to negotiate the use of our content as training data.
Transcript 0:00 Speaker 00 Cover letters. Ugh. That hurdle we all face, right? They can feel like such a time sink.
0:06 Speaker 01 Oh, definitely. And you're often left wondering if anyone even reads them properly.
0:09 Speaker 00 Exactly. But what if there was a way to make it faster? And, you know, maybe even better.
0:16 Speaker 01 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.
0:24 Speaker 00 OK.
0:25 Speaker 01 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.
0:37 Speaker 00 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.
0:44 Speaker 01 Mm-hmm.
0:45 Speaker 00 It can spit out something super basic, almost useless, or with the right guidance, it can actually give you a pretty expert starting point.
0:53 Speaker 01 That's the key, isn't it, the guidance? So let's start at the beginning. What happens if you just, you know, give AI a really simple request?
1:00 Speaker 00 OK, baseline.
1:01 Speaker 01 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.
1:15 Speaker 00 And what did it turn out?
1:17 Speaker 01 Well, pretty quickly, it generated like a standard opening. You know the type. "I'm writing to express my interest."
1:23 Speaker 00 Mm.
1:23 Speaker 01 Mention having a diverse background, passion for cultural heritage.
1:27 Speaker 00 OK, so speed is definitely there. Instant intra-paragraph.
1:30 Speaker 01 Instantly. But, and this is the big but.
1:33 Speaker 00 Ooh.
1:33 Speaker 01 It was pretty generic. Lacked any real specific details that would make a recruiter sit up and take notice.
1:39 Speaker 00 Right. It's like, OK, it looks like a cover letter, but does it say anything?
1:42 Speaker 01 Exactly. Maybe a decent starting point if you're planning to heavily edit, like a six out of 10 for potential.
1:47 Speaker 00 But not something you'd send as is.
1:49 Speaker 01 Oh, absolutely not. Maybe a four out of 10 if you just sent that. And here's where it got interesting. Um, the skills it mentioned.
1:54 Speaker 00 Ah, OK. What about those?
1:56 Speaker 01 It listed things like data analytics, requirements gathering, process improvement, project management, pretty standard business analyst skills.
2:03 Speaker 00 Sounds reasonable.
2:04 Speaker 01 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.
2:18 Speaker 00 Huh. So it pulled general skills for the role type, not the skills that specific employer said were most important.
2:25 Speaker 01 Precisely. You can sort of picture the AI having scanned like thousands of business analyst job ads online web scraping, right? So it knows the common keywords.
2:35 Speaker 00 Yeah.
2:36 Speaker 01 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.
2:45 Speaker 00 Right. That's the document that matters most.
2:47 Speaker 01 Absolutely. So that initial test showed, yeah, AI is fast, but a basic prompt gives you a basic, maybe even slightly off-target result. It's often very me-focused. Here are my general skills rather than here's how I meet your specific needs.
3:00 Speaker 00 Okay, so the simple approach isn't quite enough. What's the next step then? How do you get better results?
3:05 Speaker 01 This is where super-specific prompts come in. That seems to be the crucial difference.
3:10 Speaker 00 Super-specific. Makes sense.
3:11 Speaker 01 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.
3:20 Speaker 00 Okay, so how do you structure that? What goes into a super-specific prompt?
3:24 Speaker 01 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.
3:34 Speaker 00 Tell me more.
3:35 Speaker 01 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.
3:45 Speaker 00 Okay.
3:46 Speaker 01 Second, you draw a parallel between that specific thing and your own worker's studies. Show you understand their world and how you fit in.
3:53 Speaker 00 Ah, connecting your value.
3:55 Speaker 01 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.
4:05 Speaker 00 That's a much stronger opening. Very targeted. What about the body paragraphs?
4:10 Speaker 01 Following that model, paragraph two focuses only on the number one skill from their list. Give details, examples.
4:16 Speaker 00 Just the top skill.
4:17 Speaker 01 Just the top skill. Then, paragraph three does the exact same thing, but for the second most important skill they listed.
4:24 Speaker 00 Laser focus.
4:26 Speaker 01 Totally. And the closing, keep it short, direct.
4:29 Speaker 00 Right, so you're basically reverse engineering a great cover letter structure into the AI prompt.
4:35 Speaker 01 You got it.
4:36 Speaker 00 Can you give an example of what that prompt might actually look like, say, for that British Museum job again?
4:41 Speaker 01 Sure, so you could try something like this.
4:44 Speaker 00 Yeah.
4:44 Speaker 01 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.
4:54 Speaker 00 Okay, setting the scene.
4:56 Speaker 01 Focus the first paragraph specifically on the British Museum's work and build a parallel to the job's top-ranked skills. Remember, organizational skills won. Make the paragraphs short and readable. The goal is simple. Write a letter that gets me an interview.
5:10 Speaker 00 Wow, okay, that's way more detailed than just write me a letter.
5:13 Speaker 01 Big difference, right?
5:14 Speaker 00 Yeah, and what happened? What did the AI produce with that level of instruction?
5:19 Speaker 01 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.
5:28 Speaker 00 Nice.
5:29 Speaker 01 It tried to build that parallel, too. Now granted, the AI might put in a placeholder example, so you definitely need to swap that out with your real experience.
5:37 Speaker 00 Of course, personalization is still key.
5:39 Speaker 01 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.
5:49 Speaker 00 So, maybe not perfect, didn't follow every single word, literally, perhaps?
5:54 Speaker 01 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.
6:03 Speaker 00 That's a significant jump. It really shows how moving from a general request to a really specific structured prompt makes a huge difference.
6:12 Speaker 01 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.
6:20 Speaker 00 Right, not copy, paste, send.
6:22 Speaker 01 Definitely not. You still need that human touch, your specific examples, your voice.
6:27 Speaker 00 Okay, so that structured, multi-part prompt is one powerful way. Are there other ways to prompt AI effectively, maybe something a bit simpler?
6:35 Speaker 01 Yes, there's another approach that's a bit more concise upfront. 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."
6:49 Speaker 00 Okay, simpler prompt, but you said upfront, what's the catch?
6:53 Speaker 01 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.
7:01 Speaker 00 Ah, okay. You provide the context after the instruction.
7:04 Speaker 01 Exactly. And then you also paste in your resume, probably best to strip out your home address and phone number first, just for privacy.
7:11 Speaker 00 How do you do that in the chat? Just paste it all in one big block?
7:14 Speaker 01 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. It keeps it organized for the AI.
7:26 Speaker 00 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?
7:36 Speaker 01 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.
7:45 Speaker 00 Right, the quantifiable achievements bit from the prompt.
7:47 Speaker 01 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.
8:05 Speaker 00 Makes sense. And I'm guessing the next step is still...
8:08 Speaker 01 Review and personalize, absolutely.
8:10 Speaker 00 Yeah.
8:10 Speaker 01 No matter which prompt style you use, that step is non-negotiable.
8:13 Speaker 00 Even if you gave it your resume?
8:14 Speaker 01 Even then, you have to check if the AI represented your experience accurately. Did it maybe exaggerate something or misunderstand a point?
8:23 Speaker 00 Yeah.
8:23 Speaker 01 And critically, does it sound like you? You need to inject your own voice, your own genuine enthusiasm.
8:29 Speaker 00 That really seems vital. It can't just be a list of facts. It needs personality. It needs to connect.
8:34 Speaker 01 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.
8:44 Speaker 00 Ah, okay. Less me, me, me, and more you, you, you, meaning the company.
8:49 Speaker 01 Kinda, yeah. It's about showing you understand their context and how you fit into their goals.
8:53 Speaker 00 So does that mean doing some homework before you even start prompting the AI?
8:58 Speaker 01 Ideally, yes.
8:59 Speaker 00 Yeah.
8:59 Speaker 01 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.
9:09 Speaker 00 What kind of questions should you be trying to answer with that research?
9:12 Speaker 01 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?
9:31 Speaker 00 Hmm, so, getting clear on those things first. How does that research then translate into using the AI?
9:39 Speaker 01 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.
9:48 Speaker 00 Okay, tell the AI exactly what each section should cover, based on your research and the job description.
9:53 Speaker 01 Precisely. You're guiding it much more closely.
9:56 Speaker 00 Could you walk us through an example of that? For a different role, maybe video marketing?
10:00 Speaker 01 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.
10:19 Speaker 00 Very direct. Then paragraph two.
10:21 Speaker 01 Paragraph two. Focus on a key strength. Let's say, "Experience with storyboarding, shooting, editing, optimizing video made me 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.
10:35 Speaker 00 Okay, specific skills and proof. Paragraph three.
10:38 Speaker 01 Paragraph three. This is the why them part. Explain why I want to work for company name. Mention something specific. I admire maybe their recent campaign, their storytelling style. Connect my skills to what they seem to value. What do I hope to achieve there?
10:53 Speaker 00 Nice. And the closing.
10:55 Speaker 01 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.
11:06 Speaker 00 That feels incredibly structured. You're really mapping it out for the AI? What kind of draft does that typically produce?
11:13 Speaker 01 You usually get something very well organized. It's concise, it's relevant, it hits all the points you specified. But...
11:18 Speaker 00 There's always a but.
11:19 Speaker 01 There's always a but.
11:20 Speaker 00 Yeah.
11:20 Speaker 01 The language itself might still be a bit... Well, AI-ish, a bit generic, maybe a little stiff.
11:26 Speaker 00 Right, it follows the structure, but the words might need work. So even with this detailed outline prompt, you still have that polishing step.
11:33 Speaker 01 Absolutely, and you can even use the AI to help with that part.
11:37 Speaker 00 Oh.
11:37 Speaker 01 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.
11:47 Speaker 00 Ah, that's clever. Get it to identify its own generic bits.
11:51 Speaker 01 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 could even tell the tone you want, more conversational, more enthusiastic, whatever fits.
12:04 Speaker 00 So you're using the AI not just to draft, but also to refine and find better phrasing?
12:11 Speaker 01 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.
12:26 Speaker 00 It really becomes like a back and forth, like you're collaborating with the AI to build the final letter.
12:31 Speaker 01 That's a great way to put it, it's an iterative process.
12:34 Speaker 00 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.
12:44 Speaker 01 Well, there is one more strategy worth mentioning, especially for situations where brevity is absolutely key. It's kind of the anti-cover letter, cover letter.
12:54 Speaker 00 Intriguing, tell me more.
12:55 Speaker 01 It's basically a super short, four-sentence introduction. Maybe five sentences, max.
13:01 Speaker 00 Hmm.
13:02 Speaker 01 You could use it as the body of an email when you apply, or maybe in those little text boxes in online application systems.
13:07 Speaker 00 Why so short?
13:08 Speaker 01 The thinking here is all about respecting the recruiter's time. They get absolutely flooded with applications and emails.
13:14 Speaker 00 True.
13:15 Speaker 01 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.
13:23 Speaker 00 Okay, get them to the resume, so what are these magic four sentences?
13:27 Speaker 01 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.
13:36 Speaker 00 Got it. Sentence two.
13:37 Speaker 01 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.
13:48 Speaker 00 Okay, short and sweet value prop. Sentence three.
13:51 Speaker 01 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 want to look.
14:07 Speaker 00 Ah, I like that. Pointing them to the proof without spelling it all out right there. And the last sentence?
14:13 Speaker 01 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.
14:26 Speaker 00 Why mention other roles?
14:27 Speaker 01 It shows flexibility and broad interest in the company, not just this one specific job. It slightly whitens the net and makes you seem like someone genuinely interested in contributing to their organization. Recruiters often appreciate that.
14:40 Speaker 00 That four-sentence approach is definitely different. Very concise, very focused on just getting that resume viewed.
14:47 Speaker 01 Exactly. It's a different tool for a different situation. Perhaps when you know time is incredibly tight.
14:51 Speaker 00 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?
15:08 Speaker 01 Right. Let's summarize. First, remember, AI is fundamentally a pattern matcher. Its first attempt might be generic. So think of it as a drafter, a template generator, not a final writer.
15:19 Speaker 00 Okay, manage expectations. It's a starting point.
15:22 Speaker 01 Definitely. Second, always. Always refine, edit, and personalize. Check for accuracy, inject your own examples, your own voice. This is critical.
15:30 Speaker 00 You just get the human review.
15:31 Speaker 01 Never. Third, give the AI context. The job description is essential. Your resume is really helpful. The more relevant info it has, the better the starting point will be.
15:40 Speaker 00 In garbage out, basically.
15:41 Speaker 01 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.
15:52 Speaker 00 Be the director.
15:53 Speaker 01 Yeah. Fifth, do that little bit of company research beforehand. Tailor the letter to their needs, show you understand them.
15:59 Speaker 00 Make it relevant to the reader.
16:01 Speaker 01 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.
16:13 Speaker 00 Good point. Readability matters.
16:15 Speaker 01 Hugely.
16:16 Speaker 00 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.
16:31 Speaker 01 That's it, exactly. It's a tool, not a magic wand.
16:33 Speaker 00 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.
16:42 Speaker 01 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?
16:55 Speaker 00 How so?
16:56 Speaker 01 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.
17:11 Speaker 00 Right. Use the tech to automate the grunt work so you can focus on the high-impact human stuff.
17:15 Speaker 01 Exactly. How can these tools help you focus your energy where it matters most? Something to think about.
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