The research reported here investigated the personality traits and resilience that a sample of Greek school principals displayed. It probed also for differences associated with sex, age and years of service in the current leadership position, as well as relationships between personality characteristics and resilience strengths. To investigate these matters we used the "The Big Five Inventory" and the "Leader Resilience Profile". The survey involved almost all school principals in the Magnesia regional government unit in central Greece. Only some of the findings echoed information found in the extant literature; indeed, our results suggest that understandings about school principals that have been developed elsewhere should not be generalized to Greece without considerable caution.