Background: Leadership development is commonly named as an outcome for experiential learning (EL) programs. Some programs have shown success at inculcating individual leadership traits. However, it is not clear whether there is a relationship between certain kinds of experiential pedagogy and specific leadership concepts or styles, such as industrial and postindustrial leadership and other concepts. Purpose: The researchers identify course-design factors associated with leadership-learning outcomes in an interdisciplinary EL program called Vertically Integrated Projects. Method: From five courses across disciplines, faculty were interviewed and syllabi and student reflections were analyzed for concepts of leadership and course designs. Findings: Students showed the most evidence of leadership learning when at least two of the three factors were present: (i) flexible and cooperative course structures; (ii) conceptual instruction; and (iii) faculty coaching. Leadership practice is distinguished from leadership learning. Implications: Leadership educators recommend conceptual instruction prior to experiential learning; the findings support supplementing that instruction with a flexible, cooperative course design to encourage leadership learning. More research is needed on the relationship between “vertical” experiences, in which advanced students mentor junior students in courses of any size, and leadership development.