I got some shock and amazement with Perplexity AI this morning to generate ideas as to how to use an image as a organization improvement tool.

I use Perplexity a lot, maybe 100 searches and researches every day and I use it as a writing aid and sometimes to create images, noting that I play professionally with my library of Square Wheels® images to generate discussions and engagement about organizational improvement.

The development of the image

Over the past few days, I asked Perplexity to develop an image to be called, “Supervisor Hellscape,” to build out my Square Wheels® metaphors as a tool for conversation, innovation and engagement about what choices we make and what we might do differently to improve supervisory worklife balance. The reality is that supervisors go through hell (this is another article I am developing) and that most feel stuck in a chaotic, unfair performance system with everyday realities of constant firefighting, unclear expectations, and conflicting metrics. Things could be better.

The image is about, “Why supervisors feel trapped,” “How to escape the performance-management hellscape,” and “One small step this week.”​ among other improvement themes.

The image below is a compendium of different metaphors around change and workplace reality. I will not expand here but note that there are a lot of things happening here that represent the many issues and problems for the average supervisor.

(My guess is that you will only identify a few of the possible metaphors.)

The reality: Not a pretty picture. (I mean, for the reality of being a supervisor.)

What is amazing is that I asked Perplexity to recommend an approach to get started making some organizational progress based on the image. Note that the image above is a Rorschach Test with there being no actual reality. But it does seems that there IS some truth here and it can generate some ideas about getting out of the ditch and up on the road. And you could do the same thing anchored to your workplace issues…

Perplexity suggested an approach to improvement:

Start by getting people talking together about “what is really going on here” and then quickly move them to define one small, shared improvement they can implement this week.

Name the mud and the alligators.

Use the picture as a safe way to surface reality: the stuck wagons, square wheels, overloaded wagons, silos, “spectator sheep,” confused supervisors, distractions, and threats in the mud and alligators below.​

Ask groups: “Where is this happening in our work?” and collect specific examples of wasted effort, friction between teams, unclear priorities, and conflicting pulls on people’s time and energy.​

Focus on one wagon, not the whole swamp.

Have each team pick one “wagon” they actually control (a process, project, or meeting) instead of trying to fix the entire system at once.​

Clarify: Who is pushing, who is pulling, who is just riding, and what “Square Wheels” (policies, tools, habits) are making that wagon hard to move.​

Turn complaints into a small, testable fix.

For that one wagon, ask: “What is one Square Wheel we can round off in 30 days or less?”

What can we stop, start, or simplify that would make tomorrow noticeably easier?​

Define a tiny experiment with a clear owner, a start date, and a simple success measure (for example, fewer rework cycles, shorter response time, less firefighting).​

Break the silence and the silos.

Use cross‑wagon conversations: bring a few people from each wagon together for 60–90 minutes to share their square wheels and small experiments.​

Explicitly invite voices that are usually in the mud or on the edges—frontline staff, “spectators,” support roles—so progress is not designed only by those riding on top.​

Celebrate progress, not perfection!

When the first experiment works even a little, make it visible and celebrate it as proof that the mud can move.​

Repeat the cycle: surface reality, choose one wagon, run one experiment, share learning—letting small, visible wins build the confidence and trust needed to tackle deeper, systemic changes.​

(note that I made some tiny changes in formatting for readability.)

The Conclusion

It seems that even AI recognizes the need for more communications within organizations to generate active involvement and group problem solving. My Square Wheels images serve that purpose elegantly and you can download the MAIN image, Square Wheels One, for free under a Creative Commons license. This means that you can use it for free!!! Check it out!

And I wonder what would happen if that challenge were run through actual program design software like SessionLab!!! 🤔 And I note that the analysis completely missed the metaphor around the two caterpillars and the butterfly and resistance to change along with Hope!

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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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