Last week, I had dinner with the CFO of a 100-person logistics company. Not FedEx-scale, but a solid growing company. Their business? Making sure their clients’ packages show up on time, every time. (Unlike my recent experiences with FedEx.) The kind of company you never think about—until your shipment’s late and suddenly you’re screaming into a tracking screen.

Over steak, we started talking cyber risk. He gave me that look—you know the one: polite smile, nodding like he’s interested, hoping I’d stop talking before dessert.

“We don’t really have much risk,” he said.

“Why not?” I asked.

“Well, we don’t handle medical records or credit cards. And the people who support our IT and cybersecurity say everything’s locked down.”

That’s when I put down my fork. Because here’s the truth:

It’s not about whether your tools are in place. It’s about whether you can prove you made good decisions.

Yes, Your IT is Under Control. That’s Not the Problem.

If your firewall is on fire, your support team will put it out. That’s their job. You’ve got antivirus, backups, MFA. Cool. That’s table stakes.

But that’s not what lawyers care about.

What they want to know is:

  • Did you make informed, standards-based decisions?
  • Can you prove you reviewed the risks?
  • Is there any record that leadership approved or rejected those risks?
  • Did you train your people to follow the rules—and document it?

Because when the breach happens—and eventually it will—no one’s going to ask about your endpoint configuration.

They’re going to ask what you were thinking.

And if your answer is “My IT team told me we were good,” then I hope your lawyer has a strong coffee budget.

The Gap You Can’t See Until It’s Too Late

Most companies think their cyber support team handles this already.

They don’t. They manage your tools. Your tech. Your updates.

What they don’t manage is the evidence that you did your part as a leader. That your business made decisions that any reasonable organization would’ve made.

This is where Cyber Liability Manager comes in.

It’s Not a Security Tool. It’s Your Legal Defense File.

Cyber Liability Manager:

  • Documents your security standards. Why you chose what you chose.
  • Tracks leadership approvals. Who knew what—and when.
  • Creates an audit trail. So you don’t have to rely on memory when you’re under oath.
  • Ensures your team is trained. And that there’s proof of it.

You don’t buy this because you think you’re getting breached tomorrow. You buy this because if it happens—and someone says you were negligent—this is how you prove you weren’t.

The “Don’t You Already Do This for Me?” Trap

This is the CFO’s blind spot. It’s easy to assume the people managing your tech stack are also building your defense case. But unless you’re paying your IT provider to gather legal-grade evidence, create governance documentation, and ensure executive approvals are timestamped and auditable—you’re exposed.

So What Finally Got Through to That CFO?

I said, “If there’s a breach, how do you plan to prove you weren’t negligent?” And I let it hang in the air. He picked up his fork. Took a big bite of steak. And said, “Yeah. We need to fix that.”

You probably do too.