Phishing Mistakes That Hurt Your Cybersecurity Awareness Program

Why Phishing Simulations Matter

Phishing simulations can be incredibly effective. When done right, they help employees slow down, trust their instincts, and build habits that reduce real-world risk.

But too many campaigns miss the mark. They’re well-intentioned but often frustrate users, erode trust, or leave people feeling like they’re being set up to fail.

To truly improve cybersecurity awareness, your phishing program must go beyond testing. It should teach through realistic scenarios, timely feedback, and consistent reinforcement. 

Top 3 Phishing Simulation Mistakes—and How to Fix Them

1. Using Obvious Phishing Emails

The Mistake:
Emails with poor grammar, outdated branding, or spoofed domains are easy to spot—and don’t reflect real threats.

Why It Hurts:
If your simulation doesn’t mimic real-world phishing tactics, it doesn’t challenge users to think critically. It becomes a checkbox exercise.

The Fix:
Use believable templates like:

• Fake DocuSign requests
• Microsoft 365 alerts
• IT Help Desk password expiration notices
• HR updates about vacation policies

Better yet, replicate recent real-life phishing attacks. Platforms like Living Security offer AI tools to help craft realistic phishing emails.

2. No Feedback—or Shaming Users Who Click

The Mistake:
Users click a simulated phishing link and either receive no follow-up or a message that says, “You failed.”

Why It Hurts:
This approach discourages learning and makes users less likely to ask questions or report suspicious emails in the future.

The Fix:
Send a short, supportive message explaining what made the email suspicious. Use tools like Microsoft 365 Attack Simulation Training to automate feedback. Reinforce good behavior by acknowledging users who report phishing attempts.

Encourage leaders to discuss simulations in team meetings to normalize learning and build trust.

3. Ignoring the Data

The Mistake:
You collect data—clicks, credential submissions, training completion—but don’t use it to guide future actions.

Why It Hurts:
Without analysis and follow-up, the simulation doesn’t lead to meaningful change.

The Fix:
Treat phishing simulations as part of an ongoing conversation. Track trends by office, department, and manager. Share insights in:

• Team meetings
• Microsoft Teams channels
• Company intranet

Use the data to spark friendly competition and highlight improvement areas.

Build a Culture of Security Awareness

Phishing simulations shouldn’t feel like traps. They should be practical tools that help build a confident, security-aware culture.

When simulations are realistic, well-timed, and followed by meaningful feedback, they do more than prevent clicks—they foster better decision-making and long-term habits.

Need Help Improving Your Phishing Program?

Want to make your cybersecurity awareness campaign something people actually learn from? Contact us today to get expert support and tools that make a difference.