One of the major obstacles that I have encountered in my experience is that organizations develop rules and policies to govern certain actions and establish guidelines for operations; however, at times, these rules cause harm to the organization.
An example: A policy on straight budget cuts, for instance, 3% cut in all time/pay. At the same time, the organization wants to accomplish some key/priority projects and initiatives. The amount of work required in a short timeframe to achieve the objectives requires that staff work overtime, hence violating the "rule-based" budget savings. However, the project or initiative may result in savings or revenue that surpasses the original 3% "savings". When the decision is made to either push the work forward or adhere to the rule, the decision many times is..."The rule says...you can't do this...you can't go over 40 hours; that's the rule! Etc."
Good, effective management will make decisions in the best interest of the organization and on a case by case basis, which at times may violate the rules because it makes business sense. A manager that only adheres to rules is not an effective problem solver, decision maker or necessarily useful in a dynamic environment.
Absurd example: One organization's rule was that staff should not have "Personal Identifiable Information" laying around that someone could misuse in some form, for instance, Social Security Numbers. This rule does make sense in protecting peoples identify from theft, so it's a good rule. However, on one occasion, an IT systems tester had created a fictitious person, "Mickey Mouse" with a SS# of "333-44-1234" and was running this "person" through the system to verify the results. One IT manager noticed a printout on the printer laying around with the Mickey Mouse and SS# and became very concerned. So, he approached the staff member to say, "You can't have this type of information laying around, it needs to be secured!" The staff member, replied that, "... it's fake, made up data to test the system!" The reply was, "We can't tell so it could be misused!" What value did this manager provide taking up two people's time and harassing an employee trying to do his/her job? This manager is VERY risk averse and his only purpose is to find things wrong, not necessarily help solve problems. Anyone can create a series of fake numbers from their head, which might even turn out to be a real social security number, but how is that useful if it can't be tied to a real name a real date of birth or other information about a real person so it could be misused?