Performance Management Blog

Teaching the Caterpillar to Fly

Teaching The Caterpillar to fly is a flexible and impactful framework for discussing change and personal growth. Here, we share some ideas.

(Updated, September 2022)

For almost 40 years, I have been playing with my Square Wheels cartoons and using this metaphor in many of training programs for managing and leading change, involving and engaging individuals and teams in performance improvement, and focusing on individual and team intrinsic motivation among other topics.

Square Wheels One images since 1993 including 2022

The evolution of Square Wheels One into its current 2022 format.

One of my most fun as well as powerful tools is around the metaphor of “the change from caterpillar to butterfly” and the paradox of how one might support and mentor change and personal growth.

I start a session with the basic Square Wheels illustration as shown below:

Square Wheels One - How might this illustration represent how things really work in most organizations

And after I get those key themes and ideas around the initial metaphor anchored down, I add in the storyline:

There are two caterpillars sitting on the wagon. A beautiful butterfly floats by and the one caterpillar says to the other caterpillar,

“You’ll never get ME up into one of those Butterfly things!”

Understand that not everyone gets the joke / story. But the KEY learning point is that people will get many different themes from that single joke. THIS is the key learning point: there IS no single answer to the joke.

From here, it just gets crazy as I identify a whole series of punchlines to the joke, not the one that most people get and simply stop thinking about.

And I discuss how this process of “stopping the thought process” which happens when one “gets” the meaning of some story. This is what often gets in the way of continuous continuous improvement at work and in personal development initiatives. People KNOW THE ANSWER and stop thinking about possibilities.

Here is a poem about the transformation of caterpillars into butterflies

Teaching Caterpillar poem

This is a solid metaphor, and one where our Square Wheels tools work beautifully.

For the FUN of It!

Dr. Scott Simmerman, Surprised 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.

Square Wheels® are a registered trademark of Performance Management Company
LEGO® is a trademark of the The LEGO Group

Dr. Scott Simmerman

Dr. Scott Simmerman is a designer of the amazing Lost Dutchman's Gold Mine team building game and the Square Wheels facilitation and engagement tools. Managing Partner of Performance Management Company since 1984, he is an experienced global presenter. -- You can reach Scott at and a detailed profile is here: -- Scott is the original designer of The Search for The Lost Dutchman's Gold Mine teambuilding game and the Square Wheels® images for organizational development.

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