Purpose: The purpose of this paper is to provide an insight into successful secondary school principals in Cyprus, focusing on identifying their actions and behaviours through the adoption of a systemic view of the quality of leadership in school organizations from multiple stakeholders (i.e. self, parents, students and teachers). Design/methodology/approach: This article is the sequel to another paper on successful principalship which was written about successful primary school principals in Cyprus. A multi-case study methodology was followed where data were gathered from a wide range of school stakeholders such as the principal, teachers, students and parents employing a common, semi-structured interview protocol developed specifically for the International Successful School Principalship Project (ISSPP) which was translated into Greek and adopted to Cyprus' educational context. Findings: This paper argues that the principals exhibit behaviors and actions such as developing relationships, being committed, being visionary and promoting a collaborative learning environment which, in combination with their passion, devotion and commitment, lead to successful principalship. Originality/value: The paper offers insights into the implications for principals' training by informing policies for recruitment and retention leading to the designing of more effective leadership training programs. (Contains 1 figure.)