This paper examines the relationship between leadership roles and skills in secondary schools in Greece. Drawing upon a sample of 124 secondary public school principals, a structured questionnaire was developed to measure leadership roles and skills. The Competing Values Framework (CVF) was adopted to operationalize the eight leadership roles. The threefold classification of skills by Katz (1974) was enriched by a fourth categorization in order to identify principals’ skills. The results indicate that Greek principals are inclined to perform the roles of innovator, director, monitor and facilitator more intensely, giving less attention to the broker, producer, coordinator and mentor roles. The importance of the innovator role in explaining the variance of two of four skill categories was confirmed; while the monitor role was strongly associated with human skills. The administrative skills were negatively associated with the facilitator role while the conceptual skills were not found to be correlated to any role. It is argued that understanding the nature of the associations could enable education policy makers and principals to pursue these roles and behaviors, thereby contributing to improvement of the school.