This paper examines the evolution of the core academic leader development course at the United States Air Force Academy. The course serves as a key part of student leadership development integrated into all four years of a student’s education and their roles within the organization. The curriculum focuses on skills, character, and critical thinking in leadership contexts. The desired effect is to engage students where they are in their development and to train them in the practice of effective, professional team leadership within their teams and the larger organization. Assessment strategies such as reflection, journaling, self-assessment, and practiced application of course material are designed to fit into students’ leadership experiences so students apply what they learn in an immediate, relevant context.