Effective community school leaders build strong, reciprocal, and sustainable partnerships to support student growth, as well as to strengthen families and communities. Developing authentic alliances among teachers, parents, and community stakeholders creates a climate of trust and positive relationships that strengthens democratic schools. Community schools are an effective way to support families and students, as well as to mobilize the support needed to engage the community in developing effective partnerships. Yet in particular, it is community school leaders who cross traditional role boundaries and build cross-cultural fluency while balancing managerial concerns, navigating politics, dealing with external accountability pressures, and fostering shared accountability. They are the people who make community schools successful, and in turn, their leadership promotes positive growth in areas not traditionally perceived as falling in the domains of education. When school leaders engage in community-organizing strategies to enhance the quality of life in neighborhoods, as well as to empower parents to take active roles in the education of their children, they inspire positive holistic changes within their schools and communities. Successful leaders make this look easy, yet the interplay of a leader’s knowledge base, skill set, and disposition is complex. A developmental model based on knowledge, skills, and dispositions that cultivate reciprocal sustainable partnerships is presented within the context of national leadership and community school standards.