AI policies are only as strong as the behaviors they shape.
And behaviors often show up first in the form of prompts.
While companies scramble to draft AI usage guidelines, many overlook the most important opportunity: teaching employees how to spot a risky prompt before they hit “Enter.”
Most violations don’t begin as malicious acts—they start with a simple copy-paste. A draft client email. A revenue forecast. A teammate’s full name.
These aren’t compliance failures. They’re prompt design failures. And unless your policy teaches employees what not to prompt, your controls are reactive at best.
What Do Risky Prompts Look Like?
Here are a few real examples of red flags that often go unnoticed:
1. Copying Sensitive Content for Rewording
“Here’s a client’s proposal deck—can you rewrite it in a more persuasive tone?”
Employees may not realize that uploading proprietary decks to public AI tools is a data governance risk—even if the goal is harmless.
2. Requesting Judgment on Colleagues
“Write feedback for Jordan, who’s underperforming.”
This blends performance management with AI interpretation—and risks leaking HR context or unfair profiling.
3. Pasting Personally Identifiable Information (PII)
“Create a template contract using John’s address and date of birth.”
In many regions, this violates not only internal policy, but also privacy regulations.
4. Prompting Around Policy Workarounds
“Rewrite this sentence to avoid triggering spam filters.”
“How do I bypass login throttling in our tool?”
Even if curiosity-driven, these show intent to manipulate or evade—common early signals of insider risk.
These prompts may seem harmless on the surface—but they reveal intent, context, and assumptions that can expose your organization to real risk. Teaching teams to recognize these red flags early is your best defense. It’s not just about avoiding blatant violations—it’s about catching subtle oversights before they escalate into security incidents, compliance failures, or reputational damage.
What Your AI Policy Should Actually Teach
It’s not enough to tell employees what tools are allowed. Effective policies go further:
- Explain what kinds of prompts are off-limits
Use real examples. Include common “grey area” language. Show what acceptable looks like too. - Highlight categories of risk
Teach employees to think about confidentiality, bias, compliance, and fairness—not just the output they want. - Connect behavior to consequences
Make it clear how risky prompts affect the organization: leaks, regulatory fines, reputational damage, loss of trust. - Give them safer defaults
Offer internal tools or redacted templates so employees don’t have to guess where the line is.
Policies that stick don’t scare people into compliance—they inform behavior. Organizations across industries are showing us how to do this: through engagement, incentives, risk exposure, and education that’s embedded in everyday workflows.
Some of these organisations include:
- Walmart: Security teams intercept risky prompts, proactively help employees correct course, and see nearly zero recidivism
- Shoosmiths: Encouraged transparent AI use with a collective bonus tied to Copilot engement
- KeepAware: Recommends teaching about AI risks at the point of use, to bridge awareness and action
- Collaboris: Discusses training on AI limitations such as hallucinations—arming users with realistic expectations, not just capabilities
Ultimately, a great AI policy isn’t just a list of rules—it’s a mindset shift. Employees need to understand that every prompt is a decision point, and those decisions have ripple effects beyond the chat window. By framing policies around real behavior, real risks, and real responsibilities, you empower your teams to think critically, not just compliantly, when using AI at work.
How Tripwire Supports Prompt Safety
Tripwire helps close the loop between policy and behavior by:
- Monitoring prompt content in real time
Flagging prompts with PII, sensitive terms, or risky framing - Providing in-the-moment guidance
Nudging users to rewrite or reconsider prompts that raise red flags - Visualizing trends across departments, teams, and tool usage—helping you tailor training where it’s most needed
- Reinforcing your policy with practical, real-world examples employees encounter daily
Policies don’t prevent risky prompts.
Awareness does—and Tripwire puts that awareness where it matters: at the prompt.
Learn more about Tripwire and request access to get started with augmenting your AI security stack.