The recent global COVID-19 pandemic has forced many institutions of higher education to place added consideration and focus on their virtual instruction, causing instructors to rethink their pedagogical approaches (Murphy, et al., 2020). While new pedagogical technologies are being introduced in higher education (Baker, et al. 2008), not all approaches have produced beneficial results (Heilesen, 2010). Could this new learning medium serve as an effective tool for student learning outcomes and comprehension of course concepts? The current study presents attempts to answer these questions through its exploration of student perceptions and impact of podcasting as an instructional tool within four undergraduate leadership courses. Through the use of podcasting as a means of supplemental content and assessment, these cases provide educators with foundational guidance and recommendations on how to most effectively implement different ways of podcasting into the classroom to achieve student learning outcomes. As we celebrate the 20th anniversary of JOLE and look ahead to the next twenty years, the authors suggest that one of the most important tasks for leadership educators will not only be to recognize opportunities presented by technological advances in teaching and learning (Gigliotti & Ruben, 2017), but also the use of these new technologies to meet the needs of a changed student population in a post-global pandemic world.