The fundamental problem in management is that the world is uncertain, and people hate dealing with uncertainty.
The result of this that they go to great lengths to provide themselves with the illusion of certainty. The Bed of Procrustres by Taleb, which I discussed previously, is primarily concerned with the problems caused by false certainty.
The problem with requiring certainty is that when you do, you fail to act. If you have to know in advance whether or not your innovation will succeed, you won’t innovate. If you have to know in advance whether or not your co-workers will perform, you won’t delegate. If you have to know in advance whether or not your idea will be accepted, you won’t put it forward.
All of the bad aspects of bureaucracy come from trying to build systems that provide certainty in a world that is by its very nature uncertain.
The more businesses I work in and talk with, the more convinced I become that the single most important management skill to develop is a tolerance for ambiguity.