The present research examines personality and resilience of primary school principals. In particular, we investigate the personality traits and resilience school principals display and the differentiation of sex, age and years of service in the current leader position of principals. To investigate the above concepts we used the «Τhe Big Five Inventory» by John, Donahue & Kentle (1991) and the «Leader Resilience Profile» created by Patterson, Goens & Reed (2009). A quantitative survey was used and questionnaires were sent to all school principals in the prefecture of Magnesia and 105 were returned. Methods of descriptive statistics for the presentation and description of numerical data as well as methods of statistical inference were used for the analysis. The results showed that school principals largely declare openness to experience as a key dimension of their personality, as well as they state high scores of responsibility as a dimension of their resilience. Through the study of literature, it appears that it haven’t been carried out in the past similar research, to study the relationship between personality and resilience, especially in the field of the education community and school principals. Thus, this factor makes the proposed study novel and unique in Greece, enhancing the scientific knowledge in this field.