This study used qualitative research procedures to evaluate the learning impact of a long term (3.5 years) leadership education program on participants' cognitive models of leadership. Situated learning theory (Lave & Wenger, 1991) and communities of practice principles (Wenger, McDermott, & Snyder, 2002) were used to develop research questions, frame the analysis, and interpret the findings. Participants were drawn from a long established collegiate student organization that has as its objective the development of the leadership capabilities of its members. As members, these students have experienced a military academy type life style while also pursuing their undergraduate studies within a large university setting. Researchers content analyzed 200 to 300 word leadership essays written by 50 student-cadets to determine their cognitive models of leadership. Three models were identified. Leading through relationships was the most frequently discussed in participants' essays (80%), followed by leading by example (70%), and finally leading by influence (5%). Implications for findings for both practice and research are discussed.