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Hey There!

Welcome to Issue #137 of Jobseeking is Hard!

Today's issue is brought to you by I Hate It Here! If you value our content, help support us buy checking out our sponsors! Show our sponsor some love for supporting Jobseeking is Hard! Thanks!

We're taking a break from our usual format this week because, over the past few months, our inbox has been filling up with questions about AI tools.

It makes sense. With the job market more competitive than ever, with what feels like 2,000,000 people applying for the same 6 roles, a lot of people are hoping AI might give them an edge (or at least help save a little effort).

So I'm sharing some of the most common questions I've been getting...and explaining, from a recruiter’s POV, why you probably don't want to put all your job search eggs in the AI basket.

This week we’re talking about:

• Why AI-tailored resumes aren’t landing interviews

• What AI gets wrong about writing cover letters

• How auto-apply tools are clogging the hiring pipeline

• Why AI-generated interview answers fall flat

And for Premium subscribers I’m:

• Answering a question about resumes without metrics. I'll explain how to show impact even when your job doesn't involve numbers.

Let’s get to it…but first

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Now, onto your AI questions…

Q: I don’t get it...I’ve been using AI to tailor my resume to specific job postings, and I’m still not getting interviews. What gives?

First, let's be clear: your resume might have nothing to do with it. It could be a ghost job. It could be pipelining candidates. It could be an internal hire that was already decided before the listing even went up. So if you're not getting interviews, that doesn't automatically mean you've done something wrong with your resume.

But if you've been using AI to tailor your resume and still getting nowhere, here's what's probably happening. If your resume wasn't working before, using AI to match it to a job posting isn't going to suddenly fix it.

The main issue with AI is bad input = bad output. AI can only work with what you give it. If your resume is full of vague bullets or generic tasks, then "tailoring" just means reorganizing and rewording the same stuff...but now with more keywords.

Recruiting is about more than just keywords. You can match a posting line-for-line, but if your resume doesn't show how you did the work or what made your impact stand out, it's not going to resonate with a human reader. That's the part AI can't do. It doesn't know the context behind your work. It doesn't know what was involved in the project you executed or what success looked like for your team. So when jobseekers tell me on coaching calls, "But I used AI," I usually ask...what did it actually have to work with?

If you've got a bullet that says "managed a team," AI might turn that into "effectively managed a cross-functional team to deliver business results." That's not impactful...that's just using thesaurus to reword it. Sure, it sounds more important...but it's still surface-level. And surface-level doesn't sell your value. Context is what matters. The "how"…not just the skill you used.

I’ve been talking about this more and more in my job search strategy calls. It’s all generic, listing the skills used but not how you used them. I'm not the only one saying this. In a recent LinkedIn poll I ran about jobseeking AI tools, one recruiter summed it up perfectly:

So yea...AI might help with formatting or phrasing. It might get your resume a little closer to the job description. But just repeating back the keywords doesn't move the needle. Clarity does. Context does. Showing how you work, not just what you do, is what makes the difference. Plus, if all of the resumes applying to the job posting say the same thing, employers can't trust that any candidate is legit.

Q: I use AI to write my cover letters. It's so simple now...why do companies even bother requiring them at this point?

There's a big difference between "submitting a cover letter" and "writing a good cover letter." A lot of people treat the cover letter as just another checkbox to satisfy an application requirement...and AI tools are great at helping with that. But if the company is actually requiring a cover letter, submitting the AI-generated one doesn't do anything. Sending along a generic note doesn't help your case. It just signals that you didn't care enough to try.

"It's not generic! It specifically mentions that I have the required experience and skills!"

Just like with resumes, the biggest issue with AI-written cover letters is that they don't go deep enough. Most tools take the job posting, pull out the key duties and required skills, and then regurgitate them back in a first-person format. "You're looking for someone who can do XYZ, and I have experience with XYZ." It's formulaic, and it shows. There's nothing in there about how you've done the work or what makes your background actually relevant to this role.

Some tools try to make it even more relevant by pulling a quote from the company website or referencing the mission statement...which only proves you went to their website. It doesn't show that you understand what they do or why this role matters to you.

If the real purpose of a cover letter was just to "express interest," then sure, AI can help. But if a cover letter is required, that's not what they're looking for. They want to know why you and why them. Repeating the job description and saying you align with their mission or culture doesn't impress anyone. It just tells them you know how to skim a website and paste keywords into a paragraph.

If you're going to write a cover letter, make it count. If you're not...you're honestly better off skipping it altogether than submitting something that looks like it came from a template generator.

Q: I paid for an AI job application tool that applies to jobs for me, even when I’m sleeping. It's supposed to increase my chances...but I'm still not hearing back. Is the ATS rejecting me?

In my opinion, these tools are one of the worst things to happen to the modern job search.

They promise to "save time" and "boost your chances" by blasting your resume out to hundreds of openings...but all they're really doing is throwing spaghetti at the wall and hoping something sticks. That's not a strategy...that's a hail mary. And it creates a mess for everyone involved.

The job search should be intentional. That's why tweaking your resume matters. That's why understanding the role matters. And we've already talked about why AI tools aren't great at that...they're bad at tailoring and even worse at context. But the bigger issue is that these tools apply to the wrong jobs. And that has consequences.

First, recruiters notice. If you apply to every role at a company (entry-level, senior-level, technical, non-technical, whatever) they're not going to take you seriously. It doesn't get you "on their radar." It makes them assume you're not really interested in this job...you just want any job. And that resume you want them to notice? They stop looking when you apply. Not because you're "blacklisted"...because they're trying to triage their time. It's a "Boy Who Cried Wolf" situation. If your name keeps showing up on irrelevant applications, they eventually stop checking.

Second, these auto-apply tools are completely clogging the hiring pipeline. Recruiting teams are already under-supported and overwhelmed. So when a role gets 1,000+ applications in the first 10 minutes...most of which are junk from bot-assisted programs...it makes it that much harder for real, qualified applicants to break through. You want to know why you're being ghosted? Why you're not hearing back even though you're qualified? Because someone's AI just spammed the job with nonsense before the recruiter had a chance to breathe. (It's also why you get rejection emails at 3am on a Sunday...because recruiters are trying to catch up.)

If you're mad you're not getting responses, don't be mad at recruiters...be mad at these garbage products trying to make a quick buck off your frustration.

And if you don't believe me, here are actual quotes from recruiters who responded to my LinkedIn poll on AI-assisted job applications:

That last one says it all. These tools are trying to beat a system that doesn't exist...and they're breaking the one we have in the process.

Don't let them ruin your chances. Be intentional. Apply to less jobs. Focus on roles where your background makes sense.

Q: I've been using AI to help with interview prep. It gives me solid answers to common questions...but I still feel like I'm bombing the interviews. Why?

You're not doing anything wrong by trying to prepare, but relying too much on AI for interview answers can actually make things worse.

I've heard this from multiple recruiters, and one summed it up perfectly in my LinkedIn poll:

That's the problem. AI can give you a correct answer...but it can't give you your answer.

A good interview response usually includes context, reflection, and a personal story that shows how you think and operate. AI struggles with that. It doesn't know your experience, so it fills the gaps with generic language about relevant skills and surface-level fluff. That doesn’t resonate.

If you're answering a question like "Tell me about a time you handled a conflict," and your response includes phrases like "I believe in proactive communication and fostering a collaborative team environment," you've already lost them.

The absence of real anecdotes is what makes AI-generated responses fall flat. If your answer lacks specifics (what the situation was, what your actual role looked like, how you made decisions in the moment, etc.) it's going to be forgotten.

AI can help you structure your thinking. It can remind you to use frameworks like STAR or help rephrase something if you're stuck. But the actual content has to come from you. If you're not using real stories, there's nothing for the interviewer to connect with.

That’s it for this week’s detour into AI-generated frustration. Got other questions about job search tools, AI, or anything else making the process more confusing than it needs to be? Hit reply or email [email protected].

I’m always collecting good questions for future issues.

Today's issue is also brought to you by Morning Brew! C’mon give it a click…it helps support your favorite job search newsletter 🙂

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Jobseekers, have a great rest of your week, and good luck with those applications!

-Adam

PS!! If you're enjoying the newsletter, let people know! Forward it, post it on social, tag me, whatever...the bigger the discussion, the better! The idea is to help as many people as possible!

About Adam- Recognized as a leading voice on hiring and workplace trends, Adam has been recruiting and providing career advice since 2003, developing high-trust relationships based on honesty with companies and jobseekers. A highly sought-after speaker, he has appeared in numerous outlets, including Bloomberg News, Business Insider, LinkedIn, and CNNMoney. You can find out more about Adam's resume and coaching services here.

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