Faculties (i.e., schools) of medicine along with their sister health discipline faculties can be important organizational vehicles to promote, cultivate, and direct interprofessional education (IPE). The authors present information they gathered in 2007 about five Canadian IPE programs to identify key factors facilitating transformational change within institutional settings toward successful IPE, including (1) how successful programs start, (2) the ways successful programs influence academia to bias toward change, and (3) the ways academia supports and perpetuates the success of programs. Initially, they examine evidence regarding key factors that facilitate IPE implementation, which include (1) common vision, values, and goal sharing, (2) opportunities for collaborative work in practice and learning, (3) professional development of faculty members, (4) individuals who are champions of IPE in practice and in organizational leadership, and (5) attention to sustainability. Subsequently, they review literature-based insights regarding barriers and challenges in IPE that must be addressed for success, including barriers and challenges (1) between professional practices, (2) between academia and the professions, and (3) between individuals and faculty members; they also discuss the social context of the participants and institutions. The authors conclude by recommending what is needed for institutions to entrench IPE into core education at three levels: micro (what individuals in the faculty can do); meso (what a faculty can promote); and macro (how academic institutions can exert its influence in the health education and practice system).