In the face of ongoing school budget cuts, increasing student numbers and national educational policy environments that demand more from schools, like it or not, school leaders are being forced to be much more market-oriented in their thinking and ways of being than at any other time before. A school is an important site for social development, and in some communities in some countries, there may be only one school in an entire community. Nevertheless, as countries continue to grapple with reduced government funding on education, many schools risk the threat of closure. And, as education consumers (parents) and users (students) demand more and better value and results from schools, competition between schools have simultaneously increased. Thus, the environment in which school leaders’ work is requiring and fostering entrepreneurial leadership. The findings reported in this paper, derive from a larger sixteen country, five continent study of 61 school leaders on the “Nature of School Leadership”. The main conclusions presented in this paper are that, male and female school leaders approach entrepreneurial in very different ways; “national culture” and “national context” significantly influences and shape the work, and thus the attitudes and behaviours of school leaders, who must embrace entrepreneurialism as an essential skill, and a response to changes in school funding arrangements, and the changing role of education in national educational policy agendas.