This conceptual paper aims to annotate the existing practices and actions of entrepreneurial education in Cyprus and Greece educational organizations taking into account the centralized school contexts. At the same time, it presents the literature background regarding the new principal's role in the 21st century in order to provide adequate school practices and actions in recent years. Specifically, it seeks to report the entrepreneurship theory and aspects concerning current practical applications in educational organizations. Consequently, the study indicates that according to the entrepreneurial education via the educational systems has the opportunity to adapt relevant programs for leading the schools in the effectiveness and improvement.