Black and minority ethnic leaders (BMEL) are greatly under-represented in English schools. About nine percent of pupils are from minority backgrounds but only five percent of teachers are from BMEL backgrounds and the proportion of leaders is believed to be lower, although national statistics are not available. In post-Apartheid South Africa, the previous racially stratified allocation of teachers to schools in their own communities has been replaced by a nominally non-racial allocation process. However, only a small proportion of educators are engaged in ‘cross-boundary’ leadership. This paper will present findings from a comparative study of BME leaders in England, funded by the National College for School Leadership (NCSL), and a parallel study of cross-boundary leadership in the Gauteng province of South Africa. The data show that the reasons for under-representation of BME leaders in England, and the limited cross-boundary leadership in South Africa, are remarkably similar. While cultural factors are powerful in both countries, there is also evidence of racism and discrimination, leading to discomfort and alienation for black leaders. The paper concludes that these problems serve to inhibit integration in both countries and to prevent BME leaders in England, and black leaders in South Africa, from achieving their full potential and acting as powerful role models for black students in both countries.