Finding Your Next Great AI Hire

Some of you might not really know who I am or what I do outside of this newsletter / Band of Insiders. Let me get you up to speed quickly. My career has brought me to many countries and many different industries, eventually I landed at Monks (formerly Media.Monks). I worked three years at Monks as Sr. Innovation Director, before resigning and going out on my own again (this was August 2024). Now I spend my time on two things: helping as many people as possible understand this tech revolution so they can benefit from it (by creating a lot of content, such as this article) and helping brands turn emerging technologies like AI, blockchain, and gaming into real strategic advantage.

So yes, I talk about this stuff all day! 🤣 In my role, helping brands, I also bump into many interesting questions. Entrepreneurs and business leaders who struggle not just with the technology itself, but with its broader impact on their people and culture. Last week I had a lovely conversation and in this call I went back to a line I used to use a lot:

Many leaders are rushing to implement as much AI as they can, everywhere! But a lot of people forget the most important part of it: people. You have to bring them along with it, get them enthusiastic about this technology, take away their possible fears and so forth.

Another question, which I want to focus on today, is not focused on the people within the company, but about hiring the right candidate(s) moving forward.

How do you make sure that your new hires are AI native, or at least AI minded/forward?

Hiring In the AI Age

Let me start by saying: YES, I strongly believe that for almost any role you need to ask candidates if they use AI. I don’t think it really matters if it’s a finance, creative or HR role, as said many times AI is a general technology and will change every industry and profession.

I also believe that hiring the right people, with the right mindset and skills, can take your business to a next level. The smaller your company, the bigger the impact this person can have.

Now in order to make this practical. Let me describe five ways to find out if someone has the right skills, mentality/mindset and ideas when it comes to AI in their (potential) new job.

1. Everyone says they use AI. Don’t stop there.

When you ask candidates if they use AI, 99% will say yes. That question has become the new “Do you know Excel?” 🤣 almost everyone claims they do..

But that answer, on its own, tells you absolutely nothing. What matters is how they use it. When I get this question in workshops or meetings, I always encourage people to follow up with: “Tell me what tools you use and how you use them.”

If their answer stops at “ChatGPT,” and they can’t explain how it fits into their daily work or what results it’s driven, that’s a red flag. It shows they’ve dabbled.. not integrated.

You’re not looking for people who use AI because it’s trendy, you’re looking for people who’ve made it part of their process.

Here’s what strong answers tend to sound like:

• “I use ChatGPT to draft initial ideas, but I also built a custom GPT that understands our tone of voice.”

• “I use automation to summarize internal documents each morning.”

• “I fine-tune prompts with brand context and train the model on previous campaigns.”

That’s the difference between someone playing with AI and someone working with it.

And notice something important, none of this requires deep technical skill. It’s not about coding or building models from scratch. It’s about understanding how to leverage AI intelligently to make your work faster, sharper, or more creative.

2. Prompting is easy. Context is strategy.

If there’s one mistake I see everywhere, it’s that people think using AI well is just about asking the right question. But it’s not. It’s about feeding the right context first, then asking the right questions.

You can prompt all day long, but if the model doesn’t know what it’s working with, it’s guessing. It’s like asking someone to design a campaign without showing them your brand book.

This is where true AI literacy begins in my opinion. Not in prompt engineering or “hacks”, but in context engineering.

The best candidates understand that AI’s output is only as good as the input. Aka shit in shit out 😉. They take time to prepare. They know how to upload documents, build a company knowledge base, or reference previous campaigns before asking the model to do anything.

They don’t start with:

“Write me a social post about our new product.”

They start with:

“Here’s our tone of voice, audience personas, and examples of what’s worked before. Now write me a social post about our new product.”

That’s context engineering and it changes everything.

This is also the answer for people wondering how to differentiate in a world where “everyone has access to ChatGPT.” If everyone uses the same model, then differentiation starts with context. What you feed it, how you shape it, and the custom systems you build around it. Your company’s voice, data, and workflows become the competitive advantage.

Anyone can use ChatGPT. But only those who design their own context layer (custom GPTs, structured brand inputs, and fine-tuned knowledge bases) will stand out. That’s where the magic (and value) begins.

So when you’re interviewing, go beyond “what tools do you use?” Ask:

“How do you get the best results from your AI tools?”

Strong candidates will talk about feeding data, context, and examples. Other ones will say, “I just ask ChatGPT.”

3. Beware of AI dependency.

There’s another pattern I’ve started to notice, especially among younger generations entering the workforce: they trust AI too much.

They ask ChatGPT a question, get an answer, and that’s it.. case closed. If GPT says “go left,” they go left.

That’s dangerous. Because AI is confident, not always correct.

The best professionals use AI as a sparring partner, not a boss. They don’t just accept what it gives them.. they challenge it, question it, and sometimes completely ignore it.

That’s the mindset you want in your company. People who are AI fluent, not AI dependent.

And here’s the thing: sometimes following your gut, even when it goes against the data, is exactly what leads to breakthrough moments. The difference between good and legendary often comes down to those decisions that didn’t make perfect sense on paper, but felt right. And that’s exactly the kind of intuition you want inside your company, people who know when to trust data, and when to trust themselves.

It’s the same with people who have “crazy” ideas. Everyone tells them not to do it, and they do it anyway and in hindsight, that’s what changed everything. Most of the biggest companies, products, and creative leaps in history started as something AI (or any logical system) would’ve probably rejected.

So when you’re hiring, look for the ones who argue with the machine, the ones who are willing to trust intuition, to follow a hunch, to take a risk. Because that’s where the breakthroughs happen.

AI should augment human thinking, not replace it. The real danger isn’t AI taking our jobs, it’s people losing their ability to think critically, creatively, and courageously because they stopped questioning it.

4. Hire for curiosity, not credentials.

If there’s one trait that’s becoming priceless in this new era, it’s curiosity. My favorite trait out there if you ask me!

AI is changing so fast that whatever skill someone mastered last year might already be outdated. You can’t build a future-ready team by hiring people who know today’s tools, you need people who love learning tomorrow’s.

This means that your best hires might not be the ones with the longest résumés, but the ones with the shortest learning curve.

You can hear it in the way they talk about their work. Curious people light up when they explain something new they’ve tried, a workflow they automated, a model they tested, or a strange experiment that didn’t quite work (but taught them something anyway).

When interviewing, try asking:

“What’s the most interesting thing you’ve learned using AI in the past month?”

If they have a story, even a small one, that’s a good sign. If they struggle to think of anything, that’s your answer too..

No one can keep up with this pace of change by waiting for training programs or corporate memos. The people who thrive will be the ones who teach themselves, explore without permission, and share what they discover. Curiosity is the answer if you ask me.

AI has turned learning into a daily act. So build teams that are obsessed with figuring things out and not because they have to, but because they can’t help themselves.

5. Hire people who know how to manage AI agents.

Until now, most of us have focused on using AI as a tool, typing prompts, generating outputs, maybe automating small tasks. But that’s already changing.

We’re entering a new phase where AI won’t just assist us, it will act for us. Autonomous agents that can plan, execute, and coordinate tasks across tools and systems are becoming part of daily work. And soon, every team will have them.

That means the real skill isn’t just how to use AI, but how to manage it.

You’ll eventually need people who understand what to delegate to machines, how to give the right objectives, how to measure results, and when to intervene. It’s a new type of leadership, one that blends human judgment with algorithmic precision.

Think of it this way: Just like managers once had to learn how to lead humans with different personalities and strengths, tomorrow’s managers will need to lead agents with different capabilities and limitations.

Some will be analytical, great at crunching data. Others will be creative, generating content, visuals, or ideas. And just like with human teammates, the outcome depends on how well they’re directed, coordinated, and aligned.

I understand that this is a completely new skill and it’s not something that a candidate will specifically have on their resume. So the answer is maybe looking for people who are great communicators, who understand that we are moving to an AI agent world. People who think in systems, design workflows, and are already exploring how to make agents work together effectively.

Because in a few years, every brand will have both human employees and digital ones. The companies that thrive will be the ones with managers who can get the best out of both.

To Summarize - The 5 Ways to Find Your Next AI Hire:

1. Everyone says they use AI, don’t stop there. Dig deeper to see how they use it. You’re hiring for mindset, not toolset.

2. Prompting is easy. Context is strategy. The real differentiation begins with how well someone feeds, structures, and builds around AI.

3. Beware of AI dependency. You want thinkers, not followers. The best people question the machine and sometimes go against it.

4. Hire for curiosity, not credentials. Tools change fast. The curious adapt faster.

5. Hire people who can manage AI agents. The future belongs to orchestrator, those who know how to lead both humans and machines.

Closing Thoughts

If there’s one thing I hope you take away from this, it’s that hiring in the AI age isn’t about chasing tools, it’s about building a new kind of culture.

Because, as I said earlier, this is as much a cultural revolution as it is a technological one.

So when you hire, don’t just look for people who can use AI. Look for people who can think with it, challenge it, and eventually lead it.

And I can’t stress this enough this isn’t just important for the future of your company, it’s essential. Upskilling your current team and hiring the right new people isn’t just how you get ahead of your competition, it’s how you survive the next few years.

Because this wave of technology won’t wait. The companies that thrive will be the ones that build cultures where humans and AI grow together, curious, adaptive, and fearless.

If you want to talk more about how to prepare your teams for this next chapter, feel free to send me an email at [email protected], or message me directly in the WhatsApp community (click). I’d love to hear your thoughts!

Much love,

Funs ❤️ 

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^{Over the years, I’ve navigated industries like advertising, music, sports, and gaming, always chasing what’s next and figuring out how to make it work for brands, businesses, and myself. From strategizing for global companies to experimenting with the latest tech, I’ve been on a constant journey of learning and sharing.}

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