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Both in Canada and globally, medical schools are prioritizing diversity in medical education. The ensuing development of innovative approaches to augmenting the representation, comfort, and success of students from under-represented groups has been increasing. Curricula have also expanded to better prepare graduates for the realities of effectively meeting the needs of a diverse patient population. Leadership has however, not kept up with this progress. Evidence shows that diverse leadership teams develop innovative solutions to complex problems, recruit and retain the best talent, and remain relevant to the communities they serve. Our international conference workshop included a literature review on the current state of diversity in medical education and in leadership for medical educators, and case-based models of lived experiences to initiate conversations in three different facets of diversity to stimulate reflection, engagement and discussion. The oft-forgotten side of the conversation in conference offerings, the audience’s perspective, was purposefully included in planning the workshop and presenters adhered to this principle throughout the session. Participants recognized the importance of addressing diversity with leadership in medical education. Themes included the need for communication training, cultural education, sharing these data more broadly with faculty in medical education and continuing these conversations. A final theme “we will never represent all minorities”, led us to a conclusion that a culture of inclusivity and not diversity would be required to successfully meet this challenge.