What strategies and support are effective for shifting the mindset of expert teachers to become expert e-learning teachers? This chapter outlines the process followed in a large polytechnic institution to introduce online and other technologies to begin to replace the traditional with more flexible, blended alternatives, delivered through a commercial course management system (CMS). Integral to the process was a matrix, devised to assist the academic development unit when working with faculty to make decisions about the degree of e-learning appropriate for their purposes. The matrix has guided the incorporation of technologies for teaching across the whole institute. The chapter outlines the institutional support that was provided for the different levels on the matrix, which enabled expert teachers to retain control over a quality learning experience for their students, and briefly explores some of the issues that arose and lessons that were learned.