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Define: "Square the circle" in Business
Fiscal Threat Level
HIGH
Multi-headcount capital waste
CWO Pro-Tip
"Demand the impossible request in writing. Print it out and frame it above your desk."
What HR thinks it means:
Attempting to resolve a problem that is seemingly impossible or involves fundamentally contradictory requirements.
What does "Square the circle" actually mean?
"Management asking you to violate the laws of physics and network latency on a zero-dollar hardware budget."
How HR uses it:
"We are asking the engineering team to square the circle by delivering the update ahead of schedule without increasing costs."
How you actually use it:
"The client wants military-grade encryption with zero performance overhead, so I guess I'll just try to square the circle."
By The Chief Waste Officer
18 years in the corporate trenches quantifying waste so you don't have to.
Published: 2026-06-12