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Leaders need to promote and to engage in divergent thinking if they are to be effective in a world of diverse cultures. One of the critical challenges that leaders face today is how to move beyond a merely theoretical agreement to accommodate diversity and instead use diversity as a strategic lever that propels innovative ideas and solutions. The American Red Cross learned, through its response to Hurricane Katrina, how ill prepared it was to provide a suitably diverse response to the crisis. "During the days and weeks after the storm, language and cultural barriers created serious miscommunication, misunderstanding, and mistrust between the largely white volunteer corps and the [diverse] residents of the gulf region" (Asirvatham, 2007). As a result, the American Red Cross was not able to provide support to all those who needed it. At that time, both the leadership and the organization appeared not to have the necessary cultural competence or the divergent thinking to respond to the diversity of the victims of Hurricane Katrina. Since then, the American Red Cross has been asked some difficult questions by members of the House of Representatives and has engaged in a process of reflection and change ("Red Cross Makes," 2006). In this chapter, we review the current portrait of diversity among the leadership of the not-for-profit sector in North America. Then, we describe some leadership practices that current and aspiring leaders in the sector need to develop. We discuss what we might do to enhance diversity of thought and practice in the sector. We focus, in particular, on integrative thinking, a recent and exciting approach to rigorous thinking (Martin, 2007). We conclude with a description of an interesting initiative developed by the Maytree Foundation, which is designed to increase diversity in the leadership of the greater Toronto area. We have also included some questions that aspiring leaders in the not-for-profit sector should consider as they think about working in this challenging sector.