But it's supposed to, on closer scrutiny (books later anyway.. in TGH you're supposed to believe in the apparent machiavellian complexity).
The "devious complexity" turns out to hide gross inefficiency.
Jordan compared it once to the Nazi leadership: a maze of chaos, duplicate responsibilities, fierce rivalries etc. One hand does one thing unknowing the other pulled in the other direction.
It was often a miracle they achieved anything (and that "miracle" was often the civil servants). It's mostly the same with the Shadow.
It's mostly chaos and despair the DO wanted. In the end it all comes down to placing Rand in the right extreme mindset of desperation to stand a chance to sway him to His side.