This study serves to contribute to the growing literature on the effectiveness of diversity trainings. Previous studies on diversity training have produced inconclusive results for diversity training goals, evaluation techniques, and success. These studies rely largely on quantitative methods and large data sets looking at representation, biases, and economics. This study examines the impact of diversity trainings from a different lens. Specifically, in a society that increasingly adheres to a post-racial ideology, diversity trainings can serve as a tool to deconstruct the basis for racial power and privilege and expose the persistence of racism in the workplace. This qualitative, inductive study allows diversity trainers and managers to discuss in-depth their views on diversity and diversity training. Diversity trainers delineated five diversity training models, all of which discuss power and privilege in different ways or not at all. The presence and nature of this discussion becomes a product of a diversity trainer’s personal beliefs and the culture of the organization where training will occur. Manager interviews showed that individual differences in racial awareness entering the training can mediate how managers respond and react to diversity training material. The combination of the training model, organizational culture, and individual racial awareness combine to determine whether or not individual and institutional change around racial power and privilege will occur. Overall, power and privilege is not a common feature of diversity trainings, however diversity training can be used to further this discussion and fight against racism. A model is proposed that presents a way for diversity trainers to combine diversity training models to promote organizational goals, as well as counter post-racial ideology to create critically inclusive and egalitarian workplaces. Moreover, suggestions are made for researchers to better evaluate diversity trainings in the future, so as to truly determine the extent to which diversity training can be used to further organizational goals.