The field of critical theory within organizational theory discusses different specific situations in a middle manager´s work life. The focus often lies within the private sector and a gap can be found in research in the public sector. Universities are among the most complex environments in the public sector, and the middle manager position, the prefect, becomes even more complex than in other organizations. The purpose of this paper is to look at the dilemmas and paradoxes that middle managers in higher education, handle as prefects. We aim to uncover the conflict between interests, values and ideas that creates organizational hypocrisy. The research has an emancipatory philosophy with an inductive approach, which has led to ten interviews with prefects in the south of Sweden. The findings indicate that there are dilemmas in working as a collegial leader and that a paradoxical situation arises between what people see as valuable attributes in a prefect and what they want and need. There is also a paradoxical relationship between the feelings about a decoupled organization depending on who in the hierarchy is exploiting it. There are also findings that support the fact that the extensive amount of administrative duties for prefects generates hypocrisy. The research also found dilemmas concerning individualistic employees. Since the combination of organizational hypocrisy, paradoxes, dilemmas and prefects has not been researched before, this can be an interesting insight in how these may coexist.