This qualitative, phenomenological study investigated the lived experience of military leaders who led the repeal of the Don’t Ask, Don’t Tell (DADT) Policy in the United States military. With a traditionally, conservative, male-dominated leadership culture in the United States military, little is known about the lived experience of those assuming the position of change leaders in institutionalizing the repeal of DADT. To gain insight into the lived experience, ten military leaders were interviewed using an in-depth, semi-structured, open-ended format. Eligible participants, who were either military retirees or veterans at the time of the study, had served in different branches of the Armed Forces and were involved in leading the repeal of DADT. An analysis of the interview transcripts revealed the following themes which emerged out of the experiences shared by the military leaders: (1) extension of the workday while shifting priorities, leading to stress; (2) creation and fostering of a change ready environment while reviewing and assessing the organization’s culture; (3) thorough comprehension of the change vision; (4) troops’ education and training while being engaging and respectful; (5) a commitment to change; (6) collaboration and consultation with leadership; and (7) authenticity as a change leader. As the military continues to implement successive rounds of controversial change in an effort to promote diversity and inclusion, these findings will benefit future military change leaders faced with leading upcoming change initiatives. Future research is recommended to explore how resultant affected emotions of both military change leaders and service members, involved in future controversial change, influence their decision of making the military a career.