Perhaps the greatest challenge facing educators of today is to create and sustain high-quality educational environments for low-income students and students of color. The Boston Pilot Schools Network, a network of eleven small, innovative schools within the Boston Public Schools, can be a model for other schools and districts as to how to create schools in which students of color can achieve at the highest levels. There are several factors that contribute to the success of Pilot Schools. Pilot Schools operate within the Boston Public Schools, but have autonomy from the district over budget, staffing, governance, curriculum and assessment, and the school calendar. Pilot Schools use their autonomies and increased flexibility to organize their schools to meet two conditions known to support high student achievement--creating environments where students are well known to their teachers and providing teachers with adequate time to collaborate. Pilot Schools also use their autonomies to engage parents in the school, and parent engagement is linked to high student achievement, especially among students of color. Another proposed reason for the success of Pilot School students is that most Pilot Schools actively talk about diversity, and these conversations influence the structures, staffing, professional development, pedagogy, and curriculum of the school. The goal of this paper is to show the broad range of how and why Pilot Schools engage in these conversations. After presenting information on the history of the Pilot Schools, this paper describes research that examines the impact of diversity conversations in schools and the negative consequences for students when those conversations are silenced. Next, the results of a study examining how Pilot Schools think about and engage in diversity discussions is described. The paper concludes with a discussion of implications for schools to develop the ability to engage in diversity conversations. (Contains 3 footnotes.)