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Leaders manage their schools in a context of conflicting racial and political sentiments. As they engage stakeholders, leaders employ strategies and selective messaging to garner support from varied audiences who maintain disparate values and interests. At the same time, they do so amid an increasingly marketized environment, forcing leaders to grapple with competing priorities. This empirical paper examines how race operates in leadership and stakeholder engagement as leaders navigate competitive and tumultuous educational and sociopolitical landscapes. Through a qualitative case study of leaders in charter management organizations (CMOs), I investigate how national and local politics interact with CMO efforts, how CMOs leaders engage stakeholders, and how leaders invoke race in that process.