Purpose: The purpose of this paper is to explore a broader understanding of the role of Cypriot school principals' personal identities, through a values system perspective, when exercising their leadership. Design/methodology/approach: A multicase study methodology was followed with five school principals, representing five different leadership styles. In each case, an in-depth investigation of the school principal's personal identity was undertaken. School principals' personal values were explored during interviews, staff meetings and daily activities observations, as well as through the use of the think-aloud protocol method. This study utilized the Schwartz Theory of Basic Human Values, as well as the Pashiardis--Brauckmann Holistic Leadership Framework, as the guiding theoretical framework. Findings: School principals' personal identities in Cyprus seem to influence, to some extent, their daily leadership practice. However, particular factors associated with the context in which they live (social identity) and work (professional identity), seemed to be affecting the personal values embedded throughout their personal identities. Research limitations/implications: Five school principals are not enough to make generalizations on the relationships between leadership styles and values. However, through this paper, the authors sought to provide examples on how school principals' personal identities influence their leadership practice. Practical implications: The findings highlight the important role and attention to school principals' personal identities, beyond the core management and leadership courses. The findings also shed light on the importance of looking more closely at contextual elements "outside" and "inside" the school and to what extent these could influence school principals' personal identities. Originality/value: This paper offers insights into school principals' personal identities, through a values system perspective, and how these personal identities influence their leadership practice.