Military operations are, arguably, especially mistake-prone, because militaries aren’t like other organizations. A normal bureaucracy has a job, and it does that job all the time. Militaries, on the other hand, tend to spend most of their time not really engaged in their main purpose: fighting wars.
Teles noted James Q. Wilson’s observation about the fundamental difference between a peacetime army and a wartime army. In peacetime, it’s easy to observe inputs but impossible to observe the output -- which is to say, how ready your troops are to go out and kick some enemy butt on the battlefield. When you get into a war, this completely reverses. In the chaos of battle, it’s very difficult to know exactly what your people are doing. On the other hand, it’s relatively easy to observe whether they killed the people they were supposed to kill and took the territory they were supposed to take.
That means that the people who advance in a peacetime army are, unfortunately, not necessarily the same people you want around when the shooting breaks out.
Megan McArdle on why armies mess up so often. I liked this quote from Steven Teles, “In wartime, you want people who would rather ask for forgiveness than permission. In the peacetime army, it’s the opposite.”
The same applies to companies. Being in wartime is very different from being in peacetime, from the CEO level on down. Ben Horowitz writes nicely about the difference for CEO's in his great book The Hard Thing About Hard Things.