Abstract Background Experiential education is paramount to clinical instruction in medicine. During teaching rounds, faculty can assess medical knowledge and clinical reasoning while modeling evidence-based patient care and effective communication. This study aimed to describe observed traits common across faculty who contribute to favorable learning environments. Design Students completed an Internal Medicine (IM) Student Chief elective at a midwestern United States Academic Tertiary Care Center in which M4s aided Clerkship leadership in near-peer teaching and communicating with students. Chiefs participated in rounds for experiential learning in clinical teaching. For this qualitative, descriptive study, M4s were asked to provide at least three “pearls of wisdom,” on observations about teaching and learning in reflective essays during two consecutive academic years. Twenty-nine M4s participated in the elective and submitted 238 pearls. The research team undertook document review and qualitatively analyzed content of Chiefs’ reflective essays. Detailed codes were organized into primary and secondary themes by each author, and then re-evaluated until they reached consensus. Through thematic analysis, we identified faculty traits students found conducive to learning. Results Three primary themes emerged: Attributes, Autonomy, and Achieving Engagement. Conclusion Experiential educational encounters are transformative to developing new physicians. Chiefs highlighted positive aspects of teaching rounds described previously including providing clear expectations, promoting goal setting, engagement, and instilling confidence. They also valued humor, recognizing cognitive overload, displaying humility, listening skills, and mentorship. While one attending cannot replicate all described effective techniques simultaneously, faculty development that promotes refining these approaches may improve the clinical learning environment for all learners.