Security training is often treated like a checkbox — a task to complete, rather than a tool to reduce risk. And it’s easy to see why. Cyber insurance providers require it, auditors ask about it, and leadership wants proof it’s been done.
However, going through the motions doesn’t necessarily mean the training is effective.
In my work with clients across industries and team sizes, I’ve seen a familiar pattern: a training video, a quick quiz, and then back to business. The problem? Most real threats aren’t showing up in multiple-choice questions. They’re landing in inboxes, Slack messages, browser pop-ups, and phone calls — often looking exactly like the tools your team uses every day.
In this article, I’ll walk through the common pitfalls of traditional security training and what it looks like when it actually works.
What Doesn’t Work in Security Awareness Training
Most companies don’t start with a strategy. They start with a requirement.
When the goal is compliance, the result is usually passive training that checks a box without changing behavior.
Here’s what I see most often:
- Generic videos that don’t reflect real workflows
- Rigid policies that interrupt daily work
- Phishing tests that feel more like traps than training
- Content that doesn’t feel relevant or relatable
Too often, phishing simulations are built to catch people off guard — clever bait, frequent tests, and a “gotcha” moment when someone clicks. But this approach can backfire. People stop trusting their inboxes. They report everything, even legitimate messages. Eventually, they disengage entirely.
That response isn’t stubbornness. It’s a sign the training isn’t working for them.
You can’t expect meaningful behavior change from a one-size-fits-all program. Effective training meets people where they are — and makes security feel like support, not punishment.
What Actually Works: Relevant, Real-World, People-Led Training
The most effective training doesn’t start with rules. It starts with relevance. When I lead awareness sessions, I skip the policy slides and begin with one question: “What’s the last sketchy message you got?”
That question opens the door. Because once people connect what’s happening in their personal lives — fake billing alerts, spoofed tech support calls, AI-generated phishing emails — to what’s landing in their inbox at work, it all starts to click.
Here’s what we’ve found works best:
- Phishing tests that are realistic and well-paced
- Live sessions where teams walk through real scenarios together
- Relatable stories that people actually remember
The goal isn’t perfection. It’s pattern recognition — helping people pause, assess, and make better decisions under pressure. That kind of judgment doesn’t come from scare tactics. It comes from:
- Real-world examples people can relate to
- Space to ask questions and talk through risks
- Training that encourages curiosity, not shame
And yes, AI is making this even more critical. Today’s phishing emails are clean, well-written, and contextually convincing. Attackers can reference fundamental organization changes, mimic vendor communications, and even clone internal writing styles. That’s why we focus on building human instinct, because filters can’t always catch what people can.
Good Security Shouldn’t Slow Teams Down
All of this works best when your broader security setup supports it.
I’ve worked with clients who require users to re-authenticate constantly or juggle multiple authenticator apps. The result? Frustrated teams, written-down passwords, and more risky workarounds.
Multi-factor authentication (MFA) is still one of the best defenses out there, but it has to be configured for usability:
- Context-aware prompts based on device or location
- Fewer interruptions for trusted logins
- One consistent, simplified flow
Passkeys are also gaining traction — secure, device-based credentials that eliminate the need for passwords entirely. They’re promising, but adoption is still in its early stages of growth.
Security that’s intuitive, consistent, and built around how people actually work is far more effective than a system that gets bypassed out of frustration.
You Don’t Need a Bigger Budget. You Need a Smarter Approach.
Before you invest in another platform or longer training modules, ask this: Is your current program actually changing behavior, or just meeting a requirement?
Here’s where to look:
- Completion and engagement rates
- Real (not just over-reported) threat reports
- Incident trends over time
- Employee feedback and behavior shifts
Improvement doesn’t require a complete overhaul. Start small, focus on what’s useful, and iterate as you go. Progress beats perfection, especially when it comes to helping people stay alert, informed, and empowered to act.
Ready to build security training that sticks?
Let’s talk about how to make security work for your people, not against them.
Learn more about our cybersecurity advisory services.
At SC&H, we help companies build people-first security programs that reduce risk without adding friction. Whether you need better phishing protection, smarter MFA implementation, or more effective training, we’ll meet you where you are and help you move forward.
