There are probably a million different ways for it to go bad.
There is a theory that gets posted here from time to time that As hire As and a few Bs that get through the filter, Bs hire Bs and a few Cs get through the filter, and so on down the line until you have hired people you really shouldn't have.
The other theory is promote until incompetent.
My guess is much more mundane, when you hire middle management they act like middle management. Which works as long as Their sphere of responsibility and control is well defined. When you need to cross cut concerns middle management actively fights against it. All most like using inheritance for code reuse and having deep inheritance hierarchies.