A natural consequence of the maturation of emergency medicine (EM) as a discipline has been the aging of the emergency physician (EP) workforce and a growing gap between its most senior educators and the newest generation of medical school graduates entering residency training programs. Awareness of this phenomenon has led to considerable discussion about the perceived dissonance in values and expectations between generations of educators and learners. At the March 2009 Council of Emergency Medicine Residency Directors (CORD) Academic Assembly, the principal author led a workshop on the challenges faced by EM educators in training residents and medical students from the demographic groups commonly known as late Generation X (Gen X) and Generation Y (Gen Y). A diverse group of nearly 100 EM residency program directors (PDs), associate PDs, and EM faculty members attended the workshop, one of four similar breakout sessions exploring best practices in EM residency training. After a didactic presentation and review of the literature on the definition and characteristics of the four generations present in the EM workforce today, participants engaged in a discussion of issues encountered by cross-generational teachers and learners, shared their insights and experiences with various educational interventions, and formed a consensus of recommendations for successfully addressing this phenomenon. The working group reconvened with the general CORD membership at the conclusion of the Academic Assembly to report on and further discuss the findings.