Successful reintegration into society after incarceration through employment can reduce recidivism and increase desistance. Post-incarceration employment opportunities typically require employers to provide training and support to ensure success, especially if the work entails supporting a potentially challenging population. In the Bay Area of California, one initiative enables individuals with a history of incarceration to contribute to the support of people previously experiencing homelessness. This necessitates alternative approaches to training. While motivational interviewing has been utilized successfully in many settings, little is known about its applicability to caregiver training at a permanent supportive housing site. In the Second Chances, Empathetic Care Program, motivational interviewing was explored as a supplemental caregiver training for previously incarcerated individuals with low literacy levels working with previously homeless residents.