Across all kinds of organizations, including schools, a prevailing discourse values leadership that pursues new ideas, new knowledge, and new practices that promise to improve performance and service. Educational leadership is, accordingly, being pressed to reshape itself to become more entrepreneurial and to promote the idea of the “enterprising self.” Profound challenges to the purpose of educational leadership are bound up with this, however. They include questions of both meaning and values around the ideas and practice of entrepreneurial leadership. This chapter examines the discourse of enterprise and entrepreneurialism, and then considers the scope for responding to and shaping this discourse and the nature of entrepreneurial leadership through the ideas underpinning democratic entrepreneurialism and adaptive strategies. Implications for principal preparation and development are suggested, including the importance of problematizing entrepreneurial leadership and engaging leaders and aspiring leaders in dialogue around the diverse varieties and progressive possibilities of entrepreneurialism.

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