Abstract: In this article, we analyze the work of the Teaching Supervisor in the public network of the State of São Paulo (Brazil). In their mediating activity between the State Department of Education and the School Directors, such workers experience contradictions inherent to their functional attributions and the incongruities of educational policies. The analysis was performed based on the speeches collected through focus groups, and the theoretical framework used was that of Psychosociology and Psychodynamics at Work. The role of the supervisor could then be related to the tension between supervising or supporting, as well as to meanings that oppose autonomy and heteronomy, recognition and non-recognition. Conflicts, suffering, and defensive strategies were considered overriding for the analysis of the work, which takes place in a context of reconfigurations of educational policies and models of management and organization of the educational system, under the molds of managerialism and State Reform. Paradoxical injunctions, present in managerialism and the prescribed tasks of the teaching supervisor, produce effects on work, subjectivity, and health. Identity conflicts and impediments to the meanings of activities are forged, thus understood as predominant factors for psychological suffering, stress, illness, and/or defensive processes of the division of the self Ver menos