Do executive coaches have the skill sets necessary for effective partnership with Black leaders? Such inquiry remains unexamined, yet research from similar disciplines—such as education, medicine, and counseling—casts doubt. Drawing on these findings, a between-subjects experiment sampled 105 White coaches in the United States and examined their willingness to have “difficult conversations” with Black clients. The study investigated two questions in particular: (a) Do coaches provide less critical feedback to Black clients than they do White clients? and (b) Do coaches engage in fewer diversity-based conversations with Black clients than with White clients? The study found that, as hypothesized, coaches opted to sidestep cross-racial conversations that centered on diversity and development. More specifically, Black clients received more support but less challenge, less constructive feedback, and less time devoted to areas of development than did otherwise identical White clients. Coaches were also twice as likely to provide diversity-related feedback to White leaders than they were to Black leaders. Multiple implications hold for the coaching community and its clients of color. First, findings suggest Black organizational executives may be robbed of developmental opportunities offered to White executives. And, second, results indicate U.S. coaching-certification programs may not be adequately preparing their practitioners to navigate diversity dynamics with Black clients.