Steven Wright is a funny guy so I thought to adapt the thinking of Steven Wright on Square Wheels® — How would he view this reality?
I’m playing with AI like many of us. And our AI Tinkerers Club started a thread asking about AI and humor — it is complicated because so much humor is based on human experience. Interesting.
SO, I started asking Perplexity, my preferred AI engine, about how comedians might view various things and then asked a few questions about their probable views on “Square Wheels,” the name of the series of images I created over 35 years ago to use as metaphors in organizational development facilitations. Ricky Gervais may not have liked them. But Stephen Wright and Robin Williams would have… so, here is what Perplexity did to generate Wright’s probable reactions to the Square Wheels training materials:
Steven Wright, known for his deadpan delivery and surreal one-liners, would likely approach the concept of Square Wheels with his signature blend of absurdist humor and clever wordplay. Here are some potential one-liners he might say about using Square Wheels to generate a humorous perspective on how things really work in most organizations:

- “Our team uses Square Wheels for problem-solving. We make a lot of progress, but only downhill.”
- “I tried to reinvent the wheel. It turned out square. Now my car only rolls smoothly when the road is bumpy.” (This is pretty abstract but accurate!)
- “My company uses Square Wheels for brainstorming. We roll around in circles, but it’s never smooth and stopping is really easy.”
- “I put Square Wheels on my unicycle. It makes balancing easier and, now, I can fall in four different directions.”
- “They say Square Wheels help you think outside the box. I’m still trying to figure out how to get things out of the garage.”
- “I installed Square Wheels on my office chair. Now I’m really cornering the market.”
- “My car with Square Wheels gets great gas mileage. It barely moves.”
- “I tried Square Wheels on my bicycle. Now I’m always two steps ahead of myself.”
- “I put Square Wheels on my treadmill. Now I’m going nowhere even faster.”
- “They say Square Wheels generate new ideas. So far, I’ve only come up with better suspension systems.”
These one-liners capture Wright’s style of taking a concept such as Square Wheels and exploring its absurd implications, often with a twist of logic or unexpected perspective. Funny stuff, because if you are not actually involved in the chaos, organizations sure can be funny to watch.
Wright’s approach blends the idea of literal square wheels with the metaphorical use of the concept in problem-solving and creativity, resulting in the kind of surreal humor Wright is known for.
- A playful comment on the irony of inefficient processes: “Are we enjoying ourselves yet?”
- A remark on the contrast between effort and results: “Who needs efficiency when we have determination?”
- A quip about postponing solutions: “I suppose those round wheels are earmarked for next quarter’s budget.”
- An observation on resistance to change: “Why fix what’s broken when we can just push harder?”
- A comment on misaligned priorities: “Looks like our Monday strategy meeting in action!”
- A humorous take on tradition versus progress: “Who needs advancement when we have tradition?”
- A remark on missed opportunities for improvement: “I think they overlooked the ‘work smarter, not harder’ memo.”
- A light-hearted comment on physical effort due to inefficiency: “At least they’re getting their daily exercise!”
- Your personal favorite, highlighting a common workplace attitude: “We’re different. We push our wagon uphill!”
But my personal favorite would be:

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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.
Here is a link to a press release about The Search for The Lost Dutchman’s Gold Mine teambuilding exercise and its 30 years of positively impacting people and performance.
Square Wheels® is a registered trademark of Performance Management Company
The Search for The Lost Dutchman’s Gold Mine is a trademark of Performance Management Company
Square Wheels and Lost Dutchman images © Performance Management Company, 1993 – 2024. All rights reserved.







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