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Abstract Background: The murder of George Floyd created national outcry that echoed down to national institutions, including universities and academic systems to take a hard look at systematic and systemic racism in higher education. This motivated the creation of a fear and tension-minimizing, curricular offering, “Courageous Conversations,” collaboratively engaging students, staff, and faculty in matters of diversity, equity, and inclusion (DEI) in the Department of Health Outcomes and Biomedical Informatics at the University of Florida. Methods: A qualitative design was employed assessing narrative feedback from participants during the Fall semester of 2020. Additionally, the ten-factor model implementation framework was applied and assessed. Data collection included two focus groups and document analysis with member-checking. Thematic analysis (i.e., organizing, coding, synthesizing) was used to analyze a priori themes based on the four agreements of the courageous conversations framework, stay engaged, expect to experience discomfort, speak your truth, and expect and accept non-closure. Results: A total of 41 participants of which 20 (48.78%) were department staff members, 11 (26.83%) were department faculty members, and 10 (24.30%) were graduate students. The thematic analysis revealed 1) that many participants credited their learning experiences to what their peers had said about their own personal lived experiences during group sessions, and 2) several participants said they would either retake the course or recommend it to a colleague. Conclusion: With structured implementation, courageous conversations can be an effective approach to create more diverse, equitable, and inclusive spaces in training programs with similar DEI ecosystems.