We analyze the Milgram experiment from original perspectives offered by the theoretical work of Moberg, Werhane, Chugh, and Bazerman on social construction, mental models, and bounded awareness. Our thesis is that there are important synergies for the next generation of ethical leaders based on the alignment of modified or adjusted mental models. This entails a synergistic application of moral imagination through collaborative input and critique, rather than “me too” obedience. We argue that the ways in which the experiments are framed, the presence of an authority figure, the appeal to the authority of science, and the situation in which the naïve participant finds herself or himself, all create a bounded awareness, a narrow blind spot that encourages a climate for obedience, brackets out the opportunity to ask the moral question: “Am I hurting another fellow human being?” and may preclude the subject from utilizing moral imagination to opt out of the experiment. Similarly, in commerce, many moral failures can be traced to narrow or blinded mental models that preclude taking into account the moral dimensions of a decision or action. In turn, some of these moral failures are caused by a failure to question managerial decisions and commands from a moral point of view because of mental models that construct a perceived authority (translated – faultily – as truth or wisdom) of managerial team or leadership. We conclude that these forms of almost blind obedience to authority are correctable, but with difficulty.