The AI Hiring Paradox: What Managers Really Want When They Post "AI Skills Required"

Across industries, job postings increasingly require AI experience, but a fundamental mismatch exists between what employers are asking for and how they evaluate it. Adam and Andy tackle this head-on, starting with the hiring manager who knows AI matters but isn't deeply fluent themselves. How do you assess a skill you don't fully possess?

The answer, they argue, comes down to asking candidates about real projects, not tool lists. Can they explain what they built, why AI was the unlock, and what they struggled with? The level of someone's challenges reveals their level of sophistication. For candidates, the advice is equally direct: build something with AI before you walk into the interview. A prompt workflow, a research project, a personal tool. The ability to narrate that process, including what failed, is what separates genuine fluency from buzzword familiarity.

For managers still unsure, Andy offers a practical hack: transcribe the interview and ask an LLM to assess the candidate's AI proficiency. Let the technology help evaluate the technology skills. 

What is AI First with Adam and Andy?

AI First with Adam and Andy: Inspiring Business Leaders to Make AI First Moves is a dynamic podcast focused on the unprecedented potential of AI and how business leaders can harness it to transform their companies. Each episode dives into real-world examples of AI deployments, the "holy shit" moments where AI changes everything, and the steps leaders need to take to stay ahead. It’s bold, actionable, and emphasizes the exponential acceleration of AI, inspiring CEOs to make AI-first moves before they fall behind.

Andy Sack (00:02.92)
This is AI First with Adam and Andy, the show that takes you straight to the front lines of AI innovation and business. I'm Andy Sack, and alongside my co-host Adam Bratman, each episode we bring you candid conversations with business leaders transforming their businesses with AI. No fluff, just real talk, actionable use cases, and insights for you.

Greetings, Adam, and all our listening, listening audience. today's episode is about sort of the rise of AI hiring and what we term the AI hiring paradox, which is like there's suddenly all these jobs that are people are hiring for where the manager is looking for.

not just a marketing person, but someone who's an AI first marketing person. And when they do that, in this episode, we want to answer sort of what they're looking for, how you as an individual can can apply and excel in job in job postings like that, and give you

Andy Sack (01:19.538)
What am I doing here? I just got lost.

Okay, so we need to edit that. in today's episode, we're we we want we want to tackle the AI hiring paradox, which is there's suddenly an influx of new job postings that have AI buzzwords attached to them, like AI first marketer, as an example. And we in this episode, we want to give guidance on what business leaders are looking for when they post that, as well as as a job applicant, what you can do.

To excel when applying for those jobs. And lastly, we we want to talk about when when how managers can assess the AI fluency of job applicants. So the AI hiring paradox episode. Adam, you have anything you want to add as I launch into this? Or should I just keep rolling? All right, so

Adam Brotman (02:19.072)
No, I think you should just keep rolling. I I'll I'll jump in.

Andy Sack (02:22.194)
So let's start with suddenly like as I mentioned, managers in also in all industries are they're not just looking for any employee. They're not just looking for a head of ops or a head of supply chain or

Ahead of marketing. They're looking for people that are AI-first ops people and AI-first marketers. And so you'll see these in job postings. and we've spoken to CEOs where they say really AI-first skills are paramount in their hiring hierarchy. So

When you see a job posting where it says AI experience required, it's really like knowledge and fluency of the AI tool landscape that I think managers are looking for.

Andy Sack (03:21.623)
anything to add so far?

Adam Brotman (03:23.566)
No, I I think that's true. Although I would just add, you know, before you ask a question of me or we riff on something specific, I'd add that it's fascinating because I wonder the chicken or the egg, does the AI, does the hiring manager have AI fluency? And by the way, if they do, that's makes sense that they would want and almost demand that they have somebody who's AI forward and AI fluent.

in the position I could see that. I can also see someone who's not AI fluent saying, I need someone who is, but that creates that paradox you mentioned, which is like, well, how are they gonna interview for someone who's AI forward if they're not AI forward themselves? So I before you even get into anything, I just wanna point out like that's kind of an interesting paradox that, you know, is is we and we can talk about, you know,

some of those cases, like what you would do if you're the hiring manager in either case, or what you would do if you're the applicant in either case.

Andy Sack (04:22.942)
Yeah, so I think that's what we want to get into in this episode. And so let's let's talk about, you know, both sides of that coin. And let's talk about first because we see it, you know, particularly because we're working in consumer-facing industries, restaurant, retail, CPG. We often see middle-aged executives whose knowledge of AI is sort of base level. They're using it, but they're by no means experts in it. And they're

But they're aware enough that it it's it's a when hiring for a new position, they recognize the importance of AI skills to their organization and they want to add them. And so, like, let's talk about that person and what they're looking for in that scenario. Do you have anything to add to that description?

Adam Brotman (05:12.148)
No. I mean so you're saying the per you're saying the first thing we're gonna talk about is the person who it the hiring manager who is AI fluent themselves or is not.

Andy Sack (05:17.406)
The mi the hiring manager.

Andy Sack (05:22.558)
They're s they're not they're not AI first, but they're AI aware and using it, but they're not so skilled themselves. Do you have advice to that person?

Adam Brotman (05:28.024)
Yeah.

Yeah. So the Yeah, that person

Well, that person has two choices, in my opinion, in my experience. And the either one of these can work. That person might just be good enough at, excuse my language, but assessing if someone's bullshitting them or not, and has a good sense of, you know, they can they can just say, I'm looking for someone who's got these skills. And they should ask the same questions of the person, the applicant, as the AI fluent hiring manager. And the question they should ask is tell me about.

Some projects in your life right now, that either personally or in your work, if you're currently employed or your last job, whatever, it doesn't matter, it can be personal or professional. Tell me about some projects where you used AI to create some sort of either efficiency or innovation that that you're turned on by that you want to tell me about. And A, if they're not fluent, that

How are they gonna be able to tell if the person's BSing them or any good? Well, the truth of the matter is if someone's actually pretty AI fluent, they should be able to explain what they did in ways that someone who's not AI fluent could understand. Because if they really understand it themselves, they should be able to teach it. They always say you can only you're a better teacher and can only teach things if you really understand them. So that I would do. Now, that does put pressure on the non-AI fluent manager to know.

Adam Brotman (07:05.206)
Like are they using buzzwords and terms and industry terms and things that you know, they may not understand it and as is the other person BSing them or not and whatever. But they use some people just have a good radar for that. So I would say I'd still ask that question, even if you're if you're the hiring manager and you're like that you described, I'd still ask it and see what they say and see how you feel about it. The other option for that manager though is don't try to do this yourself. Like

Find somebody in your organization on your AI task force or that you, a friend of yours that you know, or you know, I'm joking when I say a friend, but I'm saying I'm I'm being half serious. Find someone who is AI proficient to ask that same question. And either one of those routes could work for that person who's not super fluent. This has to be the hiring.

Andy Sack (07:53.694)
Let me add two other suggestions, which the audience can either take or ignore. If I were not the most AI proficient hiring manager and I were trying to hire an AI-first marketer, I would say, I would, I love your question. Tell me about a project that you've worked on with AI per.

Probably personal or professional. That's a great question. I also like the question, tell me, you know, tell me the thing the top two things that you struggle with most in your AI work. Because the level of the answer to that question, I think actually reveals the level of sophistication of the employee, even if they're not of of the employee's AI skills.

And I would record the entire transcription, the entire thing, transcribe it, feed it back into ChatGPT or Claude, and ask Claude or ChatGPT, how AI proficient is this candidate? And I assure you that both Claude and L and ChatGPT will be able to support and assist the hiring manager. And that's my that's my hack on that system. All right, let's switch gears.

Adam Brotman (08:52.918)
That's great.

Adam Brotman (09:01.25)
Yeah.

Adam Brotman (09:04.918)
I like that.

Andy Sack (09:08.71)
Like what's your advice for you know mid-30 career professionals looking to stay current, like worried about falling behind? What's your advice to those people?

Adam Brotman (09:22.702)
Yeah.

Well, it's interesting because it it it dovetails or whatever you call it into the answer we just gave on the on the hiring manager side, which is don't show up to an interview that says that either you think well, put it this way, don't show up to an interview where there might be a chance or there is for sure gonna be a chance that they're gonna ask you about AI if you haven't built a cool project or process with AI recently. And and that's because

The number one piece of advice that you and I and our firm gives to any anybody when it comes to like getting AI proficient is you gotta use the AI and you gotta like build something with it. And I don't mean build a website per se or go when I say build something, it could just be build a process. It could be build like do a research project that was a you know more than just a chat bot chat interaction. Like do build a really cool task prompt workflow.

game website. My daughter does this with lovable, right? Like in other words, like anybody can do this. And if you haven't tried to do it, you're not gonna be, you're not, you're definitely not AI proficient. And so you're not gonna be able to answer that question. But if you're kind of like semi proficient or you are proficient, like definitely be prepared to show up to talk about a project you built and be prepared to talk about a little bit about like

How you built it, that's interesting, but also like what was it about AI? What was it about your understanding of AI, the modern understanding of the modern AI systems? And what I mean by that, like last six months, not like two years ago. And that you like built something kind of semi-agentic. This is the model you use, this is the system you use, this is how I put it together. And this is this was the insight I had. This is me talking as if I was the applicant. This was the insight I had about like why AI would on.

Adam Brotman (11:16.194)
something that that that you know I that I wouldn't have been able to do just being really smart or just being like hardworking that without the AI system being plugged into this thing I wouldn't have been able to do it. And if you can talk about that as an applicant, both in terms of what you did and sort of the insight you had or the idea you had, I wonder if this thing would work with I wonder if AI would help me be able to build this thing I've always wanted to do but I could never do. By the way the unlock could be you as a person. It could be like

I don't know how to code. I don't know how to design. I don't know how to create images. I don't know how to even do research in some ways. But I wanted to get to this output, this thing, whatever. And I did this thing with AI and I and this is what I did. And this is what it allowed me to do. Because what it allowed you to do is express yourself as an applicant that not only are you AI proficient, not only did you do this thing, but you could explain why you did it, how you did it, what it unlocked, and it tells you a little bit about yourself too.

It shows the manager that like, you're a problem solver and you used AI to problem solve in this way. So I think you could hit a lot of those things if you approach the interview that.

Andy Sack (12:25.65)
great great suggestion. My suggestion, equally hacky, that that the audience can either listen to or ignore. One is if they have you know, if they have in particular Chat GPT mobile app, they they could actually ask the mobile app to interview them for the position and practice interview and get feedback on their answers to interview questions.

questions for a specific job. They could take the job posting, upload it, and have Chat GPT interview them. That's one piece of advice. The other is is like you could also have the LLM say, I want to get better at AI AI oriented marketing, AI-first marketing, and I want, you know, every week I want you to give me 30 minute w X tasks

To do to accomplish in 30 minutes and do that task once a week. Those are two concrete sort of hacky steps that maybe lead to ultimately being able to complete the project that you outlined for them. So I think that's that's our advice and comments on the AI hiring paradox that seems to be appearing in corporations across America. we we wish

We think AI first employees are critical to organizations' future success. And we think the demand for those employees will continue to go up in the near term while the LLMs race ahead with their model releases. With that, thank you for listening to.

AI First with Adam and Andy. For more resources on how to become AI First, you can visit our website, www.form3.com, download case studies, research briefings, executive summaries, and join our email list. We also invite you to connect with our AI First community, a curated hub and network for business leaders turning AI hype into action. We truly believe you can't overinvest in your AI learning. Onward.