This multi-site qualitative study examined the perspectives of K-12 superintendents and principals in four districts of a Southeastern state during the implementation of a new teacher evaluation system required by the Race to the Top federal grant. Specifically, these educators' viewpoints regarding this two-year implementation's impact are compared and the superintendents' collaborative leadership efforts with principals are described. Findings include four themes: increased instructional leadership, time and training tensions, supportive superintendent strategies, and unintended consequences. This study contributes to the literature regarding improvement initiatives in school districts by studying implementation of such initiatives in smaller rural districts.