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Interest in leadership research began in early 20th century; yet the definition of leadership has been blurred, and contested. This is evident in countless leadership theoretical perspectives, models and frameworks that have been emerging and which make it challenging for aspiring leaders to learn and develop especially in this volatile age. Higher institutions, to future proof their undergraduates, have responded to this critical need, by offering either specialized leadership content or leadership communication courses, or focusing more on one discipline than the other. However, a more holistic approach, underpinned by behaviorist and constructivist theories of teaching and learning, that prepares leaders for these turbulent times is urgently needed. This teaching experience discusses the evolution, process and impact of a collaborative effort between two disciplines, Information Systems (IS) leadership content and IS leadership communication skills. University administered anonymous qualitative and quantitative post module evaluation reports show that while some students see the relevance and transference of leadership knowledge and skills to other domains, other do not see the need to learn about these skills before they begin their professional career. These findings offer valuable potholes to avoid and insights for future leadership training efforts.