In an effort to humanize the issues surrounding mass incarceration, and to foster empathy in historic site visitors, Eastern State Penitentiary Historic Site launched a pilot tour program that hired formerly incarcerated people to give tours of the building. These 15-minute tours allowed visitors to hear personal stories of incarceration alongside the history of a unique space at the prison. Preparation for the project began a year before it launched, and focused on ethical, legal, and marketing issues. Would this job re-traumatize the tour guides? How would visitors react? Planning resulted in a program that provided tours to approximately 2000 visitors led by four formerly incarcerated people in the spring of 2016. The results of this project demonstrate that museums can hire trauma-impacted educators to promote empathy, humanize difficult content topics, encourage social change in museum and historic site visitors, and transform the museum itself. A bibliography is included.