What if AI could challenge your thinking—before your audience does?

Welcome to Prompt, Tinker, Innovate—your weekly AI playground. Welcome to Prompt, Tinker, Innovate—your weekly AI playground. Each week, we don’t just explore prompts. We use them to rethink how you work.

This edition isn’t about polishing your message—it’s about pressure-testing it. Before you pitch, publish, or present, ask yourself: Is this really the strongest version of the idea?

Most people don’t.

That’s where your Challenger Persona comes in—an AI that pushes your thinking, pokes holes, questions assumptions, and flags what’s missing. Today isn’t about doing more with AI. It’s about thinking better with it.

This week’s playground: Build an AI that pushes back

Why this matters

Most of us spend our time building, writing, or pitching—rarely stopping to ask: Am I thinking big enough? Is this actually good—or just done?

Without a challenger, it’s easy to settle. You launch something decent when you could have launched something brilliant.

With a challenger, you get the feedback you wish you’d gotten sooner—from a sharp investor, a skeptical customer, or a trusted teammate. This isn’t about fixing grammar. It’s about sharpening your thinking before the stakes are too high.

Use case spotlight: AI for strategic review

What’s happening?

Early adopters are using AI for more than writing support—they’re using it as a thought partner. With a clear persona prompt, AI can act as a tough critic, thoughtful collaborator, or visionary mentor.

And it’s not just for marketing copy (though it works great there). Try it on:

• A high-stakes pitch

• A strategic plan or product roadmap

• Your new pricing model

• An email to a client or exec

• Your company messaging or positioning

Example in the real world

Some of the sharpest product teams I work with use this technique to challenge feature decisions. Founders I’ve advised run investor pitches through a “skeptical VC” prompt to refine their story. And I train marketers to simulate audience pushback—so they hear objections before they go live.

I even used this prompt on this newsletter. It pointed out that I’d buried the core idea. (It was right.)

Your AI experiment: Try this prompt

👉 Time to tinker: Copy and paste the following prompt into ChatGPT, Gemini, Claude, or your favorite AI tool.

📝 Prompt: "You are a challenger persona with a sharp eye for strategy, logic, and clarity. Your job is to review my [presentation/email/article/pitch] and challenge it with thoughtful questions, alternative perspectives, and areas where I may be thinking too small or missing the mark. Be clear, direct, and constructive—push me to improve. Here’s the content: [Insert your content]."

💡 Pro tip: Refine the output with a twist:

• “Challenge it from a customer’s point of view.”

• “Assume you’re a VC who isn’t convinced yet.”

• “Push me to make it 10x more impactful.”

Then follow up with: “Now help me rewrite it with those improvements.”

What did you discover?

Did it shift your perspective? Catch something you missed? Help you reframe a core idea? Reply and share your biggest insight—I might feature your tip in a future newsletter!