The field of evaluation has experienced greater professionalization in the areas of evaluator education and training. Growth in these areas included sensitivity to issues of diversity, with efforts to attract and retain evaluators of color. Currently, there is limited scholarship on navigating a world with more opportunity but still dealing with being Black. Motivated by our identities as Black evaluators, we explored the education, training and socialization concerns experienced by Black evaluators and the advice they would offer. Through content analysis of semi-structured interviews and the utilization of Critical Race Theory as a framework, we garnered advice to and from Black evaluators on how to (a) navigate the politics in evaluation; (b) engage in reflection and reflexivity; (c) network and collaborate; (d) mentor and bring others along the way; and (e) develop as a professional evaluator. We offer a synthesis of these findings in the discussion and articulate further implications.