The paper will present findings from an international study of the deliberative challenges, transformation of roles and relationships, and innovative responses of senior educational leaders in the context of new economy, funded by the Social Sciences and Humanities Research Council of Canada. The goal of this study was to bring to description the philosophy-in-action, the reflection-on-action, the entrepreneurial dispositions, the strategic competencies and the pragmatic insight expressed by senior educational leaders in the post-secondary sector as they effectively encounter, make sense of, and engage new environmental realities. What and how do key educational leaders think about the challenges in the context of the new economy, and what strategic orientations and practices they engage in to adapt their work and sustain their core mandate effectiveness? This paper will give particular attention to the background leadership journeys of these leaders and how they conceive of their shifting roles in the academy and larger community. The insights from interviews with 30 Vice Chancellors (Presidents) from universities in the United Kingdom, Canada and the United States will be presented.