The 7 Deadly Sins of Phishing Simulations
(and How to Fix Them)
Dear CISO,
You’ve launched phishing simulations.
Gold star for effort. 🎖️
But if they’re built like traps and not tools, they may be doing more damage than good.
The real question isn’t “Are our employees clicking?”
It’s “Are our simulations building resilience — or resentment?”
Sin 1: The “Gotcha!” Email
The Sin: Sending absurdly tricky phishing emails just to watch employees fail.
Why it’s deadly: It fosters resentment, not improvement.
Fix: Build tests that teach, not trap. If your CEO would laugh at it, you shouldn’t send it.
Research shows simulations that rely on deception without consent or context can undermine trust. (NDSS Symposium)
Sin 2: One-and-Done Tests
The Sin: Running one simulation per year and calling it a culture program.
Why it’s deadly: Behavior doesn’t change after a pop quiz.
Fix: Think habits, not events. Build cadence and repetition.
Meta-analyses show annual training has little effect; sustained, frequent engagement drives improvement. (Hoxhunt)
Sin 3: Shame & Blame Emails
The Sin: Publicly outing employees who click (“Congrats Bob, you got phished!”).
Why it’s deadly: Fear erodes reporting and hides real risk.
Fix: Replace shaming with coaching. Create psychological safety where mistakes become learning moments.
Public shaming of simulation failures correlates with lower reporting of real threats. (Gibraltar Solutions)
Sin 4: The Boring Template
The Sin: Reusing the same “UPS delivery” email 47 times.
Why it’s deadly: Fatigue sets in. Employees check out.
Fix: Diversify scenarios — HR updates, invoice fraud, CEO asks, seasonal scams. If you reuse a test, do it strategically (seasonality, repeat clickers, new business area).
One-size-fits-all simulations and repeated identical phishing templates degrade engagement. (Dig In)
Sin 5: No Feedback Loop
The Sin: Employees fail a test and nothing happens — no explanation, no next step.
Why it’s deadly: Missed teachable moments = stagnant culture.
Fix: Provide immediate, digestible feedback — show what was missed, why it worked, and how to recognize the next one.
Sin 6: Not Measuring What Matters
The Sin: Treating click rate as the only KPI.
Why it’s deadly: Clicks don’t equal resilience.
Fix: Track richer indicators:
Reporting rate of suspicious emails
Time-to-report vs. time-to-click
Who is clicking (by role/department)
Sentiment shift in employee attitude toward phishing and reporting
Sin 7: Ignoring the “Why”
The Sin: Treating phishing simulation like a compliance checkbox, not a psychology lesson.
Why it’s deadly: Hackers exploit urgency, authority, curiosity — training without context doesn’t stick.
Fix: Teach the psychology. Show how attackers work. Build reflexes, not just recognition.
Studies on social engineering highlight that persuasion tactics (authority, urgency) are central to phishing success. (arXiv)
Beyond Clicks: Culture Metrics That Matter
To shift from “gotcha” to growth:
Pulse Surveys: “I feel confident spotting phishing.”
Behavioral Analytics: Reporting rates, time-to-report, escalation patterns.
Sentiment Analysis: Employee responses shifting from “ugh another test” → “that one taught me something.”
Engagement Metrics: Not just completion, but active participation.
These belong on a culture dashboard alongside traditional rates.
Practical CISO Playbook
Here’s what you do next:
Audit your simulation campaigns against the 7 deadly sins.
Diversify templates to reflect actual attacker playbooks.
Introduce strategic reuse, not lazy recycling.
Expand metrics beyond clicks — focus on reporting and sentiment.
Close the loop: Instant feedback + coaching after simulations.
Engage employees in dialogue: listening sessions, focus groups.
Model psychological awareness — teach why phishing works, not just how.
Your Real Job
You don’t just run tests.
You build vigilance.
You enable asking the question: “Why is this email urgent?”
Simulations aren’t just lessons — they’re culture signals.
If your program feels stale, your employees might already know it.
And if they know it, so do attackers.
Sincerely,
A fellow defender who still wonders if today’s “fake” email would fool him.
Because the next breach won’t be because someone didn’t know.
It’ll be because someone didn’t feel safe enough to ask.
CISO Takeaway
Phishing simulations done poorly create annoyed employees.
Phishing simulations done right create alert humans.
Stop running “gotcha” tests. Start building habits, feedback loops, and no-shame culture.
Culture eats click-rates for breakfast.
