Predictions indicate that a large majority of the heads of independent schools in the United States will retire within the next decade. Although there is a push for a greater representation of people of color in this position, in order for people of color to be considered, it seems that they are held to a higher standard than their white counterparts. The data from this study show that there is a significant statistical difference in the percentage of recently appointed heads of color who are alumni of independent schools, as well as those who have held a senior-level position. Furthermore, a greater percentage of heads of school of color than of heads of school who are white are alumni of selective graduate schools or hold a terminal degree. Last, heads of color reported that they found it important, yet difficult, to develop relationships with the educational search firms who often serve as the gatekeepers to these highly coveted positions. The results of this study, although they call for changes which will be daunting to make, give independent schools the necessary framework to move beyond the criteria and approaches currently used to identify viable head-of-school candidates.