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Τhe aim of this paper is to study the pathogens of the bureaucratic organization of the modern Greek educational system as well as the resulting alienation and loss of identity which are relevant to teachers. At the same time, in the framework of this investigation, they were analyzed some literary works of the authors Nikolai Gogol and Franz Kafka, who, through their work, became timeless critics of bureaucracy. In the first chapter of the paper are made the clarifications of the concepts, that are necessary for the understanding of the phenomenon of school bureaucracy. Thus, it is presented the way of structuring the Greek education system and consolidating the bureaucratic organization into that. The second chapter analyzes some features of bureaucracy, such as how to create and consolidate it, as well as the pathogens it has created over time in its administration. Also, a more specific reference is made to the school units, focusing on the impact on teachers' work. The third chapter approaches three literary works by Gogol, "The Nose", "The Inspector", and "The Coat". This approach, focuses mainly on the way in which Gogol presents the bureaucracy in his works, using the literary techniques of satire and grotesque element. In the fourth chapter there is a similar approach to the literary work of Kafka, who also criticizes the bureaucracy of his time with the allegorical record of the myth. For the purposes of the survey, the projects "The Tower" and "The Trial" were selected. The next two chapters, fifth and sixth, analyze the qualitative research that has been followed to meet the needs of work. More specifically, the survey was conducted using the method of interviewing and collecting answers from teachers about how they are experiencing bureaucracy in their everyday lives. Finally, in the seventh chapter, the conclusions drawn from the elaboration of the present paper are mentioned