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As teachers of leadership, we have noticed that our students often get “stuck” thinking about leadership in overly simplistic ways that dichotomize task and relationship-orientations, often resulting in overly simplistic understandings of leadership processes. In this reflective essay, we draw upon two approaches to leadership theory—leadership psychology and discursive leadership—to consider why the leadership dichotomy occurs and provide ideas for how leadership instructors might restructure and refocus their courses to help students transcend it to develop more reflexive, contextualized understandings of leadership. We suggest four ideas for innovating leadership pedagogy: 1) rethink the typical chronological organization, 2) challenge students to identify leadership myths, 3) engage students in applied leadership contexts, and 4) emphasize leadership as a communicative practice.