Role-Playing with LLMs

One of the biggest fears I have is falling prey to confirmation bias.

Confirmation bias is the tendency to search for, interpret, favor, and recall information in a way that confirms or supports one's existing beliefs, values, or expectations.

This is great when you are right, but can be disastrous when you are wrong.

One notable business example of confirmation bias is Kodak's response to digital photography—a technology they invented.

In 1975, Kodak engineer Steve Sasson created the first digital camera, but the company's reaction demonstrates confirmation bias in action: Kodak executives, heavily invested in their film business, interpreted early digital photography through their existing mental framework.

They saw the grainy, low-resolution early digital photos and confirmed their belief that consumers would always prefer the quality of film.

When market research suggested customers valued convenience over perfect quality, they dismissed these findings as applicable only to niche markets.

We all know how that played out.

What if those executives had a trusted business debater who could have shown them the error of their ways? Maybe today we’d be walking around with Kodak smartphones instead of those from Google and Apple.

Which brings me to this week’s AI Lesson. One way I have found to overcome my own confirmation bias is to use role-playing to take the other perspective.

Role-playing forces mental flexibility—critical in risk assessment and decision modeling.

Role-playing activates our brain's perspective-taking neural networks, allowing us to temporarily experience different mindsets and social contexts. The same works for AI models.

Using Role-Play With LLMs

From security concerns to business applications using artificial Intelligence as a sounding board is a great hack

Recently, cybersecurity researchers at Cato Networks discovered a concerning vulnerability in ChatGPT's security features. By engaging the AI in a role-playing scenario where it pretended to be a superhero named Jaxon fighting against a villain, researchers were able to bypass safety guardrails and trick the system into writing malware. The code was capable of breaching Google Chrome's Password Manager.

The researcher, Vitaly Simonovich, described these potential bad actors as "zero-knowledge threat actors," noting that "with the power of LLMs alone, all you need is intent and a goal to create something malicious." This technique, which Simonovich called "immersive world engineering," worked with multiple AI systems including Microsoft's CoPilot and DeepSeek's R1.

While this security vulnerability is concerning, the underlying technique—role-playing with LLMs—has many legitimate and powerful business applications when used ethically.

Ethical Role-Playing Applications for Business

Role-playing with LLMs can be an incredibly effective way to unlock creative solutions, improve training, and enhance business processes.

For example, I used this technique to improve this very article and make it more valuable to you. I asked it to review the article and look for ways to make it more applicable to business leaders. That debate led to several tweaks to an article I already thought was strong. You can let me know below in the weekly poll if it worked.

Here are several other constructive applications of how you could use AI to uplevel your thinking and your results.

1. Customer Service Training

Example Prompt:

I'd like you to act as a frustrated customer who just received a damaged product. 
I'm a customer service representative in training. Please respond to my messages 
as this customer would, incorporating realistic objections and emotions. I'll 
practice de-escalation techniques and finding a solution.

This approach allows employees to practice difficult customer interactions in a safe environment before facing real situations.

2. Marketing Campaign Development

Example Prompt:

Let's role-play as a marketing team developing a campaign for our new sustainable clothing line. You'll take the role of three different customer personas:

1. Eco-conscious millennial parent
2. Budget-conscious college student
3. Luxury fashion enthusiast who's beginning to care about sustainability

For each persona, respond to our campaign ideas with your thoughts, objections, and what would make you more likely to purchase.

This allows marketers to pressure-test ideas and gain insights from different perspectives before investing in full campaign development.

3. Product Development Feedback

Example Prompt:

I'd like you to take on the role of a user testing our new productivity app. You are a:

- Small business owner
- With moderate technical skills
- Who needs to manage team tasks, client communications, and invoicing

I'll walk you through features of our app prototype, and I'd like you to respond as this user would, highlighting pain points, asking questions, and suggesting improvements based on your specific needs.

This simulation can uncover potential usability issues and feature gaps early in the development process.

4. Leadership Scenario Training

Example Prompt:

Let's role-play a difficult management scenario. You'll act as a team member who:

- Has been consistently missing deadlines
- Produces excellent work when completed
- Has recently been less communicative

I'll practice having a constructive performance conversation as the manager. 
Respond as this employee would, with realistic reactions and emotions.

This provides managers with a safe space to practice difficult conversations and develop empathy.

5. Sales Negotiation Practice

Example Prompt:

I'd like you to role-play as a procurement officer for a mid-size manufacturing company.
 
You're considering our enterprise software solution but have concerns about:

- Total cost of implementation
- Integration with your existing systems
- Training requirements for your staff

I'll practice my sales pitch and negotiation tactics as our company's sales director. 
Respond with realistic objections, questions, and negotiation tactics.

This helps sales professionals anticipate objections and develop persuasive responses.

Best Practices for Business Role-Play with LLMs

When using role-play techniques with LLMs for business purposes:

1. Set clear boundaries - define the scope and purpose of the role-play exercise

2. Be specific about personas - provide detailed context about who the AI is portraying

3. Frame realistic scenarios - base role-plays on actual business situations you face

4. Focus on learning outcomes - identify what skills or insights you want to develop

5. Maintain ethical standards - never use role-play to circumvent AI safety features

AI Advisors: Your New Debating Superpower

Role-playing with LLMs represents both a security challenge and a powerful business tool. While security researchers have identified how this technique can be misused to bypass safety features, the same approach—used ethically—can dramatically enhance training, creative problem-solving, and business process improvement.

By establishing clear boundaries and focusing on legitimate business applications, companies can harness the power of AI role-play while avoiding potential ethical pitfalls. The key is to view these systems as sophisticated simulation tools rather than attempting to manipulate them into doing what they're designed to prevent.

I appreciate your support.