This paper examines aspects of leadership in four Canadian and U.S. organizations that provide justice-related services to Indigenous people, focusing on the influences of culture and colonial legacy on Indigenous leadership. Located in western Canada and the Southwest United States, the agencies provide culturally sensitive and knowledgeable services to Indigenous offenders and those at risk of offending and are key initiatives in Indigenous peoples' efforts to regain sovereignty. Services include youth crime-prevention programs, legal assistance, alternative sentencing advice, prisoner education, probation and parole programs, and after-care services such as substance abuse counseling. Following descriptions of their histories and services, the four organizations are analyzed with regard to four dimensions of leadership: (1) administrative structure and the leader's position within the organization; (2) organizational environment (demographic, economic, legal, political, technological, ecological, and cultural); (3) individual characteristics reflecting Indigenous leadership qualities; and (4) leader-subordinate relationship and leadership style. In these organizations, the leader's ability to "define the reality of others" was critical to organizational survival. Indigenous leaders must have the skills and knowledge to overcome colonial attitudes and redefine Indigenous organizations as competent and worthy of receiving resources while simultaneously meeting the sometimes conflicting expectations of Indigenous communities and mainstream justice organizations. (Contains 35 references.) (SV)