Entrepreneurship in education, as discussed by Hisrich and Drnovsek (2002), is a central theme, interpreted as an initiative by school leaders to establish additional support networks (Pashiardis, 2014). In fact, in school organizations, the involvement of external stakeholders, especially parents, is emphasized as crucial in enhancing educational achievements, as supported by existing research (Balasi et al., 2023; Castro et al., 2015; Fox & Olsen, 2014; Van Voorhis et al., 2013). Despite the fact that recent changes worldwide are aiming to improve the quality of teaching and learning by strengthening the independence of individual schools, it remains to be seen whether, how, and to what extent the successful exercise of more entrepreneurially motivated leadership can succeed in the social reality of school organizations. Therefore, to better understand how successful school leaders promote entrepreneurship within their school organizations, this paper maps out the external leadership dimension and entrepreneurialism exhibited by successful school leaders in Cyprus, using case studies from a decade-long research study. The study intends to provide prospective pathways for successful external school leadership, considering the contextual perspective within which school leaders operate. The centralized education system in Cyprus, governed by the Ministry of Education, imposes directives, policies, and oversight on school organizations, limiting autonomy and disregarding unique characteristics. This paper argues that the contextually dependent nature of centralization influences the external practices of school leaders, urging them to navigate challenges related to resource acquisition and external support. In fact, the lack of decentralization hinders critical inquiry, emphasizing the pivotal role of school leaders in fostering improvement despite the prevailing conditions. Therefore, inspired school leaders in Cyprus promote external strategies for engaging external stakeholders beyond parents to address challenges and improve school organizations. Having said that, this paper contends that school leaders should explore diverse approaches for engaging external stakeholders, and that their capacity to regulate interactions depends, also, on personal values and circumstances.

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