Based on our experiences at a military service academy and the study of leadership informing administrators in overseas branch campuses, we propose a link between conceptual leadership development in these learning environments and the relevance of the four types of knowledge--declarative, procedural, contextual, and somatic for educational administrators and leadership educators. Demonstrating an appropriate and experiential frame of reference through application of the knowledge types can help inform students and educational leaders about contextual applications of leadership and affect leadership development in diverse educational settings. Our paper also discusses application challenges and impact on future learning environments. Through examination of the chosen environments we maintain that effective leader development requires a balance between institution-centered experiential exercises and learner-centered pedagogy based on the contextual learning environments explored.