In this post, I talk about how to use The Probability Prompt to get better AI search results. I wrapped it around my change story about caterpillars and butterflies. The answers AI gave were outstanding!

I was reading about how to best prompt AI engines to generate the optimal response and one article referenced Stanford research that suggested a format idea as the best structure for an inquiry:

“Generate 5 variations of this idea, each with their probability” before you frame up your question is the approach. Asking for a probability pushes the LLM to not give you a typical, safe response but to generate more creative responses. (You can find more details here.)

So, I tried it and it worked better than expected, so I will continue to ask Perplexity, my go-to AI engine, to give me alternatives and probabilities in some of my searches and suggest that you try this tactic.

How did it work? You be the judge…

Here is a link to one of my posts about my “Teaching The Caterpillar To Fly“ posts about resistance to change and other reactions to my joke and this image:

There are two caterpillars riding on the wagon and a beautiful butterfly floats by. The one caterpillar says to the other, “You’ll never get ME up in one of those things.”

Building on this prompt idea of, “Generate 5 variations of this idea, each with their probability,” I asked Perplexity:

Two caterpillars are sitting on the Square Wheels wagon and a beautiful butterfly floats by. The one caterpillar says to the other, “you’ll never get me up in one of those things.” Give me 5 responses to this situation and the probabilities of people suggesting them.

I thought Perplexity’s response was quite good, excellent actually, and you can compare these AI-generated responses with what I get in a session around managing and leading change with live participants, which I show in the blog previously mentioned. What AI did was give me some additional perspective about how people choose to process the story, and that there are real differences in thinking styles.

Perplexity:

That’s a great image—funny, layered, and metaphorically rich. People’s responses would likely depend on whether they interpret it literally (as humor), figuratively (as transformation resistance), or contextually (in a team or change discussion).

Here are five common types of responses—both what people might say and how common each type might be in a facilitated group or conversation setting.

1. The Humor Response

Example reaction: “That’s a good one! Classic fear of flying—or fear of change!”
Interpretation: They take it as a punchline first, appreciating the wit and irony in the caterpillar’s unwillingness to imagine transformation.
Estimated probability: 35% — Humor is an easy entry point and most people respond instinctively to the joke before reflection.

2. The Resistance-to-Change Insight

Example reaction: “That’s exactly what happens in organizations—people can’t imagine the benefits of change because they only see risk.”
Interpretation: The caterpillar represents employees resisting growth or transformation due to fear, lack of vision, or comfort with the familiar “wagon ride.”
Estimated probability: 30% — People familiar with organizational dynamics or coaching often default to this interpretation.

3. The Self-Reflection Response

Example reaction: “That reminds me of myself—sometimes I’m the one afraid to spread my wings.”
Interpretation: The person makes a personal connection, recognizing their own hesitation to evolve or leave the status quo.
Estimated probability: 15% — This happens when participants feel safe and reflective, especially in a facilitated session.

4. The Optimist’s Reframe

Example reaction: “Maybe one day he will—he just doesn’t know what he’s capable of yet.”
Interpretation: The caterpillar’s resistance is temporary; with support or vision, transformation is inevitable.
Estimated probability: 10% — This response blends hope with insight, typical of growth-mindset individuals or leaders.

5. The Analytical / Facilitator Response

Example reaction: “Interesting metaphor. The wagon represents old systems, the butterfly the future state, and the caterpillars are current employees—what’s blocking them?”
Interpretation: The person deconstructs the image, using it to prompt group discussion or capture themes like inertia, fear, and transformation.
Estimated probability: 10% — Most likely from facilitators, consultants, or participants used to visual metaphors like Square Wheels.

I will note that I have 21 different answers to this joke, which helps when I debrief.

The image, the lesson point, and some of the possibilities

And my Favorite Answer:

Overall, I am amazed at the level of detail and the AI’s seemingly incredible about the nuances of the story around metamorphosis and change.  Sure, I have written about this before and, sure, Perplexity can access many of my writings around this idea of there being many responses to a single story like this one.

But the QUALITY AND NUANCES OF THE RESPONSE are pretty amazing, as it relates to the story and the learning lessons themselves.

Change is a complicated thing, and there ARE so many different aspects about how perceptions and perspectives underpin an individual’s choices. It is neat to see what a good tool the AI engines can be for building some better facilitation practices and an understanding of human behavior.

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For organizations with multiple stuck teams, book a short conversation to design a program using Square Wheels across your organization, We can easily build some really great tools and courses and support systems,

For the FUN of It!

Dr. Scott Simmerman is a designer of team building games and organization improvement tools.
Managing Partner of Performance Management Company since 1984, he is an experienced presenter and consultant who is trying to retire!! He now lives in Cuenca, Ecuador.

You can reach Scott at scott@squarewheels.com
Learn more about Scott at his LinkedIn site.

Square Wheels® are a registered trademark of Simmulations, LLC
and images have been copyrighted since 1993,

© Simmulations, LLC 1993 – 2025

What I am about:

My Square Wheels blogs and website exist to equip leaders, trainers, and facilitators with practical process improvement tools along with effective organizational change tools. My purpose is to facilitate engagement and active involvement to help make work smoother and more human.

By blending change management facilitation with proven workshop facilitation techniques, team collaboration activities, and creative problem solving activities, my mission is to support organizations in designing employee engagement strategies that are both energizing and sustainable. Through accessible, sometimes free team building resources and virtual facilitation tools, my focus is on helping teams everywhere discover better ways to collaborate together, innovate continuously, and own their path to improvement.

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