Role-Play With AI To Give More Strategic Advice To Your Executives

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Now with AI, you have a 24/7 role play partner to help you think through communications challenges.

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Communications professionals are being called upon to become more strategic. But what does that really mean in practice?

Beyond writing speeches, prepping talking points, and fine-tuning tone, strategic comms professionals help executives navigate the high-stakes terrain of persuasion, positioning, and power dynamics. It’s not just about what to say—it’s about how to win with words.

The tools of the trade are evolving. Standard prompting with generative AI tools may give you competent copy. But to become more strategic, communications professionals need more than templates or a series of content suggestions. They need to sharpen their instincts, build stronger intuition for narrative dynamics, and test ideas in simulated high-stakes environments.

This is where role-play with AI becomes a powerful—and largely untapped path to mastery.

Role-Play With AI: Strategic Insight Through Simulation

Imagine this: You’re an executive communications lead preparing your CEO for a critical investor roadshow. You’ve already gathered the data, prepped the narrative, and revised the deck. But something’s missing.

That’s when you boot up your equivalent of a custom GPT—a generative AI assistant you’ve trained with internal strategy decks, past earnings call transcripts, and communication preferences of your CEO.

You begin role-playing. First, you take on the role of the CEO. You ask the AI to play the analyst from the hedge fund with a reputation for aggressive questioning. Name the analyst by name when you prompt. You can then run through a simulated Q&A session, gauging where the narrative holds and where it wobbles.

Next, you reverse the roles. You become the sparring partner, using AI as the CEO, answering the curveballs you throw and holding ground with language modeled on the exec’s past statements and values.

Finally, you become the VP of Strategy, scheduled for a meeting with the CEO. You use AI to simulate that executive, employing techniques borrowed from the persuasion expert of your choice. I like Oren Klaff—author of Pitch Anything. You can ask the AI to model his approach and show how the CEO might push back, redirect, or challenge assumptions.

You’re no longer just preparing talking points. You’re rehearsing moves in a high-stakes chess game. And each iteration brings deeper insight into strategy, persuasion, and power.

Three Powerful Ways to Role-Play With AI For Strategic Comms

1. Turn The AI Into The Executive Him Or Herself

When you role-play as the executive, you practice owning the message. You simulate how the narrative sounds when delivered from a position of authority—and you see where it lands flat.

By feeding your custom GPT with the executive’s past public statements, writing style, and business priorities, you develop a richer model of how they communicate under pressure. You start to spot mismatches between message and messenger.

This version of role-playing helps you avoid the “over-polished” or “too safe” language that drains credibility. It also helps you identify which ideas will feel native to the executive—and which ones need to be reframed or dropped altogether.

Here’s a prompt to get started:
“You are [CEO NAME] preparing for a critical investor meeting where you want to achieve [FILL IN THE BLANK]. You are using the persuasion techniques of Oren Klaff. Take this argument I’ve written and respond as the CEO would—with critique, edits, or redirection.”

This kind of back-and-forth helps you pre-test resonance—and prepare for real-time improvisation.

2. Turn The AI Into The Sparring Partner

Now step into the ring. Assume the role of the hard-nosed journalist, skeptical investor, or cautious head of HR. Have your AI act as the executive under fire—and start testing your messaging.

In this configuration, the AI becomes a resilience builder. You ask it to stay in character, respond with emotional realism, and test how well the story holds up under interrogation.

The key here is training your AI to simulate specific expert personas—like a former negotiation consultant, a media strategist, or a leadership coach. Don’t let the model float into generality.

Be specific:

“You are an executive coach trained in negotiation techniques used by [YOUR FAVORITE EXPERT IN THIS AREA]. You are preparing your client [CEO NAME] to maintain composure and redirect a conversation during a hostile interview.”

Then simulate. Ask questions. Challenge ideas. Force contradiction. Push into tension.

As the sparring partner, you don’t just learn what the executive should say—you learn how and when to pivot, concede, or double down.

3. Turn The AI Into The Group At The Next Meeting

Perhaps the most strategic use of AI role-playing is simulating the next meeting. In this scenario, you play the person across the table from the executive: the CFO, the regional MD, the voice of the skeptical customer.

You use the AI to simulate the exec’s likely responses—grounded in real data—and practice pitching ideas, making asks, or raising objections. The goal is to anticipate moves, reactions, and power plays.

Here, you become the architect of influence. You’re not just “communicating up”—you’re designing how the exec’s message travels down and across the organization.

This is especially powerful when layered with storytelling and persuasion frameworks. If you’re channeling someone like Oren Klaff, you might prompt your AI with:

“You are [CEO NAME], influenced by the narrative structure of Oren Klaff’s ‘Pitch Anything.’ Respond to this idea I am pitching as if I’m a divisional leader with limited alignment on our strategy.”

These simulations help you rehearse the true dynamics of internal persuasion and become more strategic.

It’s Not About Prompts. It’s About Training and Framing.

Too many comms professionals are stuck in “prompt world.” They rely on generic inputs and accept mediocre outputs. The real unlock comes when you build a custom AI model that reflects the voice, tone, and strategic nuance of your company.

That means feeding it with:

• Internal decks, vision documents, strategy memos
• Transcripts of all-hands calls, media interviews, analyst briefings
• Notes on communication style, decision-making preferences, and leadership values

Once you’ve given it this rich internal fodder, you don’t stop there. You then tell it what it is—not just what you want. Assign it the role. Give it the mindset. Make it a negotiator, a strategist, or a master persuader.

This framing unlocks another level of utility. It’s not just a writing tool—it becomes your rehearsal partner, narrative critic, and political strategist.

The Persuasion Playbook You Didn’t Know You Needed

The genius of Oren Klaff’s work in Pitch Anything lies in how he dissects moments of persuasion. He doesn’t just tell you what to say—he dramatizes it. He shows how power flows in a room, how to create narrative tension, how to switch frames and keep control of a conversation.

Comms professionals would benefit enormously by not just reading Pitch Anything—but by building AI models that simulate Klaff’s techniques. Let your AI be the executive using Klaff’s methods. Then test what works and what fails.

The goal isn’t to manipulate—it’s to elevate the comms function into a strategic lever that shapes outcomes, not just messaging.

Better Strategy Through Simulation

The most strategic comms professionals I know aren’t just great writers. They’re great listeners, power-mappers, and story-framers. They can see two or three moves ahead in a conversation. They anticipate what will derail alignment—or cement it.

Generative AI, used as a role-playing partner, gives you a sandbox to train those muscles.

So don’t just ask your AI for headlines. Ask it to be your CEO. Ask it to be your adversary. Ask it to challenge you.

That’s how you stop being the person who “makes things sound nice” and start becoming the one who moves things forward.