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This paper constitutes a qualitative study and a presentation of the views of the Headmasters/Headmistresses of Secondary Education school units in the Prefecture of Thessaloniki on the importance of communication as a necessary skill and as a necessary condition for effective administration and leadership. The purpose of the study is to highlight the role of the emotional intelligence and of the communication skills of the Headmaster in shaping the climate, the culture and the reputation of the school unit he leads. Specifically, by examining the views of the Headmasters/Headmistresses of various types of school units, the study seeks to record a) the leadership characteristics and the knowledge required for their term as head of the school unit to be considered successful, b) the extent to which they perceive the importance of creating their vision, and of its adoption by other persons involved in the operation of the school unit c) the communication techniques they use in dealing with diversity, with conflicts, and overall with day-to-day problems arising in the context of the school unit’s internal or external environment, d) how they manage their responsibility in shaping the school climate, e) their views on the creation of a specific school culture, and its dissemination in the local community, and f) the ways that maintain or improve the school’s reputation. The qualitative research carried out showed that emotional intelligence, empathy, active listening, the respect of personality, and effective communication in general are basic factors for the improvement of the school climate, of cooperation, of the dissemination of a realistic and clear vision, and of the creation of a culture of quality that characterizes the school and enhances its reputation.