Let me introduce you to the new team member quietly absorbing everything about your business. 

They don’t sleep. 

They don’t forget. 

They don’t ask questions. 

And they’ve never—not once—completed your security training. 

Meet: Your Employee’s AI Assistant. 

AI Doesn’t Just Observe. It Absorbs. 

Here’s what a typical Tuesday looks like: 

  • Your CFO uploads the new bonus plan into ChatGPT—“just to help with wording.”
  • Sales copies and pastes a client contract into Claude to “simplify the language.”
  • HR asks Gemini to rewrite an incident report about a termination.
  • Marketing feeds a confidential client quote into an AI tool to “make it pop.”
  • You drop your next pricing sheet into a chatbot to “tighten the messaging.”

None of them meant to break protocol. 

None of them thought twice. 

None of them realized they were leaking proprietary, regulated, and client-sensitive data into a platform you don’t control. 

What AI Sees, It Stores. 

That AI assistant? It’s not under NDA. It’s not your employee. It’s not your contractor. It’s a machine trained on prompts—and your team just made it smarter with your data. 

This isn’t fearmongering. This is happening every day. And if you’re not auditing how AI is being used in your business, you’re not running a company. 

You’re running a live feed into a liability crisis. 

“But We Use Microsoft 365. We’re Safe.” 

That’s adorable. 

Your M365 tenant is probably leaking like a sieve. 

We’ve seen it all: 

  • Chat transcripts with sensitive data flowing through ungoverned AI plugins
  • Email content being scanned, tagged, and fed into smart tools you didn’t approve
  • Teams channels with open access to AI bots ingesting client conversations
  • Copilot configured to “help” with everything—except security

All of it invisible to you—until the breach. Until the lawsuit. 

Until someone asks you: 

“Can you prove your team wasn’t leaking sensitive data to an external AI?” 

If you can’t answer that confidently, congratulations—you now have an AI-generated liability. 

It’s Time to Get a Cyber Liability Assessment. We’ll help you find out: 

  • What AI tools are being used (intentionally or not)
  • How your Microsoft 365 tenant is configured
  • Where the leaks are happening
  • What data is being exposed
  • And what you can do before your new AI assistant lands you in front of a judge

Book your Cyber Liability Assessment now. 

Before your chatbot becomes Exhibit A. 

👉 Schedule Your Assessment