This chapter explores the evolution of thinking about learning, resulting from the increasingly ubiquitous presence of instructional technology and communications technology in learning environments. It provides a short history of the pedagogical growth of technology usage. It further describes the impact of technology on the potential transformation of four-walled classrooms into global, online learning communities from a constructivist perspective, while looking at learner/teacher roles in the learning process. The Global Forum on School Leadership (GFSL) and the Global Forum on Educational Research (GFER) are introduced as applications of interactive educational technology, suitable for twenty-first century learners, teachers, and school leaders, that emphasize creation of new knowledge using exploration and collaboration through self directed, technology-enhanced learning controlled by the learner. The intent of this discussion is to explore the impact of technology on learning, and recognize the transformative power behind introducing this learning experience into school leader preparation programs.