The overwhelming rise of leadership learning programs and experiences within higher education merits the exploration and identification of best practices, reduction of limiting educational methodologies, and strategies for promoting efficient and effective leadership education has never been greater. This study explores the barriers inherent to leadership learning environments from the learner, environmental, and instructor perspectives. Qualitative interviews of leadership faculty members allowed for naturalistic themes to emerge. The transferable findings suggest that best teaching practices, including positive student-instructor relationships, critical reflection, adaptive leadership application within real-world settings, will have profound implications on the ever-growing field of leadership education and the development of the leadership learner.