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We challenge the belief that people resist change while embracing the idea that change is necessary to lead. Cultivating leaders to orchestrate conflict with deliberate intention is a skill leaders can learn. Yet, skill alone is insufficient to lead. Using three models, Communicative Intelligence, Adaptive Leadership, and Adaptive Schools, we tell the story of how we developed leaders to think adaptively and communicate authentically to collaborate across diverse communities to bring their visions to fruition. This chapter describes the models and their integration from three perspectives illustrating how we focused the cultivation of leaders. First, the personal development of their dispositions related to communication, collaboration, and systems thinking. Second we worked on developing the skills to build relationships and think politically. And third, we focused on identifying and implementing systems to address the critical issues facing their schools.