Predict the pushback: Simulate your boss to pressure test your pitch

Welcome to Prompt, Tinker, Innovate—my AI playground. Each edition gives you a hands-on experiment that shows how AI can sharpen your thinking, streamline your process, and power up your creative work.

This week’s playground: Simulate the stakeholder that could make or break your pitch

You walk into the meeting thinking your pitch is airtight. Ten minutes later, it’s dead. Not because it’s bad—but because you hit the wrong nerve.

Maybe you leaned into innovation when your boss is in risk-aversion mode. Maybe you skipped over the one metric they always ask about. Maybe you used a word that sounds like “extra headcount” and that set off alarms. The point is: even great ideas get shot down when they don’t speak to the emotional calculus of the decision-maker.

This week, you’re going to use AI to simulate that stakeholder—before you face them. Think of it as running “the meeting before the meeting.”

Why this matters

Most of the time, when we prepare for a presentation, we prepare in a vacuum—or we practice with a colleague who is too polite to give harsh feedback.

The reality is that your boss (or client) has a specific set of priorities, communication quirks, and even anxieties that need to be addressed by your pitch to successfully move forward. By pressure-testing your pitch against a hyper-specific persona, you can:

• Spot blind spots your audience will instantly notice.

• Preempt objections that normally catch you off guard.

• Reframe your message around what they actually care about, not just what you want to say.

Example: The skeptical CFO vs. the visionary CEO

The same pitch will fail with one person and succeed with another depending entirely on framing.

• The scenario: You want to pitch a new software tool for your team.

• The CFO persona: If you pitch "efficiency" and "cool features," the CFO simulation might reject it. They care about ROI, implementation costs, and contract length.

• The CEO persona: They might get bored with the cost breakdown but light up at the phrase "competitive advantage" or "market speed."

Use AI to roleplay the reception of that pitch. It’s essentially a low-stakes dress rehearsal that helps you switch from "What do I want to say?" to "What do they need to hear?"

Your AI experiment: Try this prompt

👉 Time to tinker: Build the persona. Think about your stakeholder’s top 3 priorities, biggest pet peeves, and communication quirks.

📝 Prompt: Copy and paste the prompt below into ChatGPT, Claude, or Gemini and paste your idea or pitch at the bottom.

“You are going to act as my [Job function or title: e.g., VP of marketing / skeptical CFO].

Your persona:

• Priorities: You care deeply about [insert priority 1: e.g., ROI], [insert priority 2: e.g., brand consistency], and [insert priority 3].

• Pet peeves: You hate [e.g., buzzwords, vague timelines, ideas that require hiring new staff].

• Communication style: You are [e.g., short, direct, and impatient / thoughtful and risk-averse].

Your task: I’m going to pitch an idea with the objective of [insert objective / desired outcome]. Critique it strictly from your persona’s perspective. Be harsh. No fluff.

1. What’s your gut reaction—Yes, No, or Maybe?

2. What are 3 objections or questions you’d raise in a meeting?

3. What’s missing that would make you say Yes?

Here is my pitch: [PASTE YOUR IDEA/EMAIL DRAFT/STRATEGY HERE]”

💡 Pro tip: Don't just accept the feedback—interrogate it.

1. Argue back: Reply to the AI with your counter-arguments to see if they hold up. Try: "Okay, if I responded to your objection about [X] by saying [Y], would that satisfy you? Or would you still have concerns?"

2. Ask for the cheat sheet: Don't guess what success looks like to them. Ask. Follow up with: "If you had to justify this project to your boss, exactly which success metrics or KPIs would you need to see in my pitch?"

This turns passive prep into an active strategy session.

What did you discover?

Did your “digital boss” surface something you’d missed? Did it give you a better way to frame your idea? Did it ask that one annoying question you were hoping to avoid?

Drop your experience in the comments. I’d love to hear what hit, what didn’t, and how you adapted.

Until next time...

Keep tinkering. Keep prompting. Keep pushing past obvious.

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