Supervisor Hellscape and Strategy, an image evolving from Square Wheels® Images to spark thinking about workplace issues and opportunities.
And you can say what you want about AI but it surely grabs the reality of how things are really working in this image I developed called, Supervisor Hellscape.
(This is based on my Square Wheels One image, a useful graphic you can get with a Creative Commons BY-ND license so that you can use it in your own trainings and facilitations. Click on the image below:)
Download the FREE Square Wheels One image under Creative Commons license by clicking on the image
Here is what Perplexity generated, with some of my edits to the output of course. But it certainly seems to capture the reality of what is happening based on the clues it has about how organizations really work. I asked the AI what was happening and I put the image below into the request.
The image shows a supervisor trapped in a muddy ditch, desperately calling “Help!” while senior managers ride happily on piles of unused tires, watching a beautiful butterfly they call “strategy” instead of helping him get the wagon back on the road and moving forward.
What is happening:
-
The frontline supervisor is literally stuck in the ditch, wrestling with ropes, mud, and alligators; this represents being overwhelmed by operational problems and risk while still being expected to “pull” the wagon forward
-
Behind him, teams sit on mountains of round tires—symbolizing unused ideas, resources, and local knowledge, while leadership attention is captured by the Butterfly of Strategy, that elegant little thing floating above the chaos and disconnected from the struggle.
-
A worker in the crowd has a “?” thought bubble, suggesting confusion and lack of clarity about priorities, while others seem disengaged or entertained, not mobilized to help and maybe not even seeing the issues. And note the Spectator Sheep in the background along with all the silos, representing the organizational culture.
Note that there are two kilometers of ditch
for every kilometer of road.
What supervisors and managers might say:
-
“This is what it feels like when corporate rolls out a new strategy, but I’m buried in today’s emergencies and have no support to execute.”
-
“We’ve got the talent and tools (all those tires), but the processes and priorities keep people sitting on resources instead of using them to move the wagon.”
-
“My performance is judged on getting the wagon out of the ditch, but all the attention and budget are chasing butterflies that don’t solve my immediate problems.”
What facilitators might say:
-
“This picture is a gap map between strategy and execution: the butterfly is aspiration, the ditch is reality, and the mud is all the friction in your system.”
-
“Notice how nobody is organized to help the stuck supervisor; what structures, metrics, or cultural norms in your organization keep people spectating instead of collaborating across levels?”
-
“The unused tires are latent engagement—ideas, discretionary effort, and process improvements—so what conversations or mechanisms would turn that pile of potential into traction on the road?”
Overall, I am amazed that Perplexity can “see” all this workplace reality by “observing” this image and framing this around how things are really working. Fully 90% of the above is the AI analysis, with me adding maybe 10% to highlight some of my key thinking about how things really work.
The Truth is Out There!
And I wonder what the reactions of a senior management group might be if I shared the image with them in a discussion about ideas for performance improvement.
The above IS a reality based on the research of so many different organizations over the decades, and I feel that it is finally time to make some improvements to make the work of the supervisor tolerable. At this time, it is not, with fully 70% of them being disengaged (Gallup, 2025 and others).
It is highly PROFITABLE to improve the effectiveness of organizational teams by enabling the supervisors, but that is meat for some other blogging I have done and will do, digging into the numbers.
—
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’m About:
My Square Wheels blog and website exist to help leaders, trainers, and facilitators make work smoother, more engaging, and more human. I focus on practical tools for process improvement, organizational change, and workplace collaboration that spark insight and deliver measurable results.
And I am convinced, after 30+ years of using Square Wheels®, that it is the best facilitation toolset in the world. One can use it to involve and engage people in designing workplace improvements and building engagement and collaboration. It is a unique metaphorical approach to performance improvement and we can easily license your organization to use these images and approaches.
By blending proven facilitation methods, creative problem-solving, and engaging team activities, my mission is to support organizations in building energized, sustainable cultures of involvement and innovation.
Through accessible — and often free — resources and virtual facilitation tools, I aim to help teams everywhere collaborate more effectively, innovate continuously, and take ownership of their improvement journey.
#SquareWheels #InnovationAtWork #TeamEngagement #FacilitationTools #WorkplaceImprovement #EmployeeEngagement #CreativeProblemSolving #OrganizationalDevelopment #LeadershipTools #collaboration #leadership #motivation #communications #enablement #leadership #CreativeCommons #enablingperformance #teamwork
0 Comments