This phenomenological study explores six principals' and assistant principals' military experience and leadership development. The participants were purposefully selected based on being a principal or assistant principal and having a minimum of 4 years of military service as a Non-Commissioned Officer or Officer in any United States military branch. The participants, from two counties in North Carolina, were interviewed using a semi-structured interview protocol. The resulting themes were (a) accountability to family, superiors, subordinates; (b) the need for special programs aiding with transitions; and (c) Military Occupational Specialties (MOS) versus Military Training. The findings revealed that specific MOS did not influence the participants' leadership development. However, military training influenced the leadership development from their military career to education leadership. This research extends previous investigations about military experience and principalship in the United States and Israel. The results are discussed, and recommendations for superintendents and local educational agencies are provided.