Why do armies led by carefully selected, expensively trained officers keep marching into disasters everyone saw coming? Norman F. Dixon’s answer in this 1976 classic: it is not stupidity, it is personality. After case studies of 120 years of military and naval fiascos (mostly British), he draws the profile of the leader who fails: authoritarian, allergic to bad news, in love with the plan.
The best part: the book is about the military, the conclusions are not. Swap the uniforms for suits and the analysis holds for any organization.
https://en.wikipedia.org/wiki/On_the_Psychology_of_Military_Incompetence