For generations, parents of black boys across the U.S. have rehearsed, dreaded and postponed “The Conversation,” but as their children become increasingly independent, parents must decide how to tell their black sons that they may be targets of racial profiling by the police. To keep the child they love safe, they may have to tell him that he risks being targeted by the police, simply because of the color of his skin. Is it possible for parents to frame this discussion in a way that both informs and empowers their boys? Can black boys and men rely on the police to “protect and serve” them while also recognizing that the institutional bias of our justice system presents a direct risk to their safety? How has the history of policing in the United States contributed to this need for “The Conversation” today? What lessons can we learn from our past that can inform our actions in the future?