The study examines the relation among personality and leadership styles of head teachers in primary education, and how these two factors affect their attitudes and beliefs about management of change. For conducting the specific study quantitative methods were used for collecting data. In specific, for the needs of the study, a representative sample of 160 Cypriot head teachers was selected. Head teachers were asked to complete three different data instruments: Each head teacher completed a) The Personality Inventory of “The Big Five Factors of Personality (Costa & MacCrae, 1997), b) The Leadership styles questionnaire “The Four Frames of Leadership” (structural, human resource, political, symbolic) (Bolman & Deal, 1992), c) The statements for a scenario for management of change, constructed by the researcher, in order to examine head teachers’ attitudes and beliefs about management of change. In addition, the teaching personnel of each head teacher of the sample (approximately 2000 teachers), also completed the leadership styles questionnaire “The Four Frames of Leadership”, concerning their head teacher. All data was elaborated by SEM (Structural Equation Modeling), for extensive examination of the relations of the examined factors.