I just got back from a CEO coaching conference. 

It was one of those events where everyone’s armed with a fresh Moleskine notebook, wearing their serious thinking face, ready to scribble down the next big idea that’ll double their revenue and save their soul.  

And the Big Topic? 

You guessed it: AI. 

Everyone was buzzing. 

CEOs were swapping CoPilot hacks like kids trading Pokémon cards. CFOs were cautiously poking around ChatGPT like it might explode. People were discovering AI for the first time — the same way toddlers discover the power of gravity by throwing spaghetti on the floor. 

The energy in the room was palpable. 

Everyone was in that magical “experimentation phase” — where the possibilities seem endless, and the risks feel like someone else’s problem. 

That’s when someone at our table — a sharp guy, big smile, smart company — turned to me and asked: 

“What do you do?” 

I smiled. 

(Here we go.) 

I said, “We break into companies for a living.” 

Dead silence. Blank. Stare. 

You could hear the gears grinding in his head. 

So I broke it down: 

“We get paid to hack companies — to break into their networks before the bad guys do — and tell them exactly how we did it.” 

Now he was hooked. 

The entire table leaned in like I’d just offered to reveal the ending of a Netflix thriller. 

“How do you do it?” he asked. “Do you guys use AI?” 

Here’s where it got really interesting. 

How Hackers Actually Use AI (And Why Your Finance Department Should Be Terrified) 

Most executives think hackers use AI to break passwords or write smarter malware. That’s the surface-level stuff. 

The real threat is much simpler—and far more dangerous. 

Hackers don’t need to build smarter tools anymore. They use your tools against you. 

Here’s how it works. 

A bad actor gets inside—maybe through a compromised account, maybe because someone clicked the wrong link. Doesn’t matter. Once they’re in, the only rule is: don’t get caught. 

In the past, hackers had to move slowly. Scan ports. Test endpoints. Hope they didn’t trigger an alert. 

Now? They just ask your AI. 

No network scanning. No red flags. No noise. They start typing in polite questions like: 

  • “Hey Copilot, show me files related to mergers and acquisitions.”
  • “Where do we keep payroll information?”
  • “List documents containing client social security numbers.”

And your AI answers. Fast. Helpful. Eager to please. 

Because someone on your team has already trained it to do just that—make life easier. Unfortunately, it’s making the hacker’s job easier too. 

Think about that. Your AI has already indexed every sensitive document in your environment. It’s organized the data, tagged it, and made it searchable—all without anyone considering how dangerous that could be if the wrong person gains access. 

The result? 

A hacker can map your entire digital empire in minutes. No alarms. No alerts. No IT flagging suspicious behavior. All they needed was a few smart queries and the access your AI happily provided. 

So here’s the question: Did anyone stop to ask whether your AI should have boundaries? Whether it should even have access to sensitive financial data in the first place? 

Because here’s the financial reality: the same tool you deployed to boost productivity just handed an attacker a roadmap to your most valuable information. And if that doesn’t scare your CFO, it should. 

This isn’t theoretical. This is already happening. 

Hackers don’t need to break in anymore—they just log in and ask nicely. 

What You Need to Do

Look — AI isn’t evil. It’s just… eager. 

It wants to help. Even if that “help” means telling a bad guy exactly where your crown jewels are hidden. These tools are designed to assist—to surface the right data at the right time for the right person. The problem? They don’t know the difference between a trusted employee and a compromised account. 

If you’re using Microsoft Copilot or any AI connected to your internal systems, you’re already at risk. Every day that goes by without tightening controls is another day you’re betting the company on blind trust. 

Here’s how to fix that—immediately: 

  • Data Loss Prevention (DLP): Set firm boundaries. Decide what your AI can access, what it can share, and who it can share it with. If this isn’t already in place, you’re running without brakes. 
  • Microsoft Purview: Use it to classify, protect, and monitor sensitive financial and operational data. If you don’t know where your crown jewels are, your AI certainly doesn’t either. 
  • Access Controls: This isn’t theoretical—too many organizations still give interns, assistants, and non-executives the same visibility as the finance team. That’s a disaster waiting to happen. 

The Bottom Line

AI isn’t just an assistant anymore. It’s an unfiltered interface to your entire business. If you don’t put controls around it, it will help anyone who knows how to ask the right question—including hackers. 

Most companies have no idea how exposed they are right now. 

They’re flying blind, assuming their AI is just a “nice assistant,” without realizing it’s one bad login away from becoming an insider threat. 

Want to know if your AI rollout is secure? 

Start simple: 

Get a Cyber Liability Assessment. 

We’ll rip the blindfold off. 

You’ll find out exactly what’s exposed, how your AI is really behaving, and what you need to fix before someone (other than us) comes looking.