Although multiple consensus statements have called for large-scale efforts to improve clinicians’ communication skills regarding a variety of difficult conversations in medicine, this goal will be difficult to attain because there are no readily scalable, validated communication skills training programs for clinicians. However, novel applications of existing technologies and approaches grounded in learning science can overcome the scalability barriers. Moreover, future advances in virtual reality and artificial intelligence are likely to greatly enhance the possibilities for communication skills training programs. The purpose of this paper is to propose a scalable, theoretically grounded method to train clinicians in advanced communication skills in medicine. First, we summarize four key principles of adult learning relevant to communication skills training in medicine. Second, we discuss recommended practices to design effective technology-enhanced educational interventions, with an emphasis on achieving high amounts of user engagement. Third, we synthesize these principles into a framework for a web- and videoconference-based platform for teaching advanced communication skills in medicine. Once developed, this low-cost, scalable training platform has the potential to allow thousands of clinicians to acquire the advanced communication skills needed for difficult conversations in medicine.