This chapter examines an initiative to create educational technology (ET) Champions and leaders within a higher education institution in Singapore. It examines how the concept of communities of practice was applied to an initiative for transforming teaching and learning through educational technology. Instructional designers coached ET Champions in the principles of creating learning objects who later returned to their respective colleges to work with other lecturers. ET Champions progressed through five stages, which included peripheral, legitimate, core, strategic and transformational membership. Each stage required support and guidance within the community.