So you’ve got a training program.

Your IT team told you it was important, so you signed off on it. Now, every so often, your employees sit through a “cyber awareness” session or get hit with a surprise phishing test.

Check the box. Done. Right?

Not even close.

Here’s the truth nobody tells CEOs and CFOs: most training programs are security theater. They look good on paper, they make you feel like you’ve done something, but when it comes time to actually defend your business, they don’t hold up.

Why? Because training has to tie directly back to the controls that protect your business. If you’re teaching employees in a vacuum—without linking it to the actual safeguards you’ve invested in—then your training isn’t defense. It’s busywork.

And let’s talk about simulated phishing. If you’re still running it, here’s a wake-up call: it doesn’t work. In fact, according to one study, simulated phishing actually made people more likely to click the malicious links. Imagine paying to make your employees worse at spotting attacks. That’s where a lot of businesses are today.

So what does work? Training that’s anchored in reality.

  • If you’ve deployed multi-factor authentication, your employees need to be trained on why it matters and what it looks like when an attacker tries to trick them into bypassing it.
  • If you’ve invested in data encryption, your employees need to know how their behavior supports that control—and how a mistake could undo it.
  • If you’ve got endpoint protection, employees should understand what it catches and what it doesn’t.

Because here’s the dark reality: eventually, someone will get past your tools. When they do, your employees aren’t just the first line of defense—they’re also your last.

And if regulators, insurers, or lawyers come knocking after a breach, they’re not going to be impressed that you had “cyber awareness” on your calendar. They’re going to ask for evidence.

Evidence that your training mapped to your actual security stack.

Evidence that your team understood not just what a phishing email looks like, but what to do when MFA requests start coming rapid-fire.

Evidence that you trained on the standards you’re legally and contractually required to defend against.

Without that? You’re not compliant. You’re not secure. You’re exposed.

So yes, you can say you “have training.” But if all you’ve done is check a box, don’t expect it to save you.

Because in cybersecurity, box-checking doesn’t stop lawsuits. It doesn’t get insurance claims paid. It doesn’t keep your business running.

The only training that matters is the kind that proves you did the right thing—before the breach, before the cyber insurance denial, before the cyber personal injury attorneys show up.