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 applicabiltiy 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. The researcher provided three in-person trainings over one month addressing basic motivational interviewing concepts to nine caregivers working at a permanent supportive housing site in Oakland, CA. While caregiver knowledge of motivational interviewing did not increase after the training when measured with pre- and post-training true/false questions, there was an increase in knowledge demonstrated by answers to an open-ended post-training question with all caregivers having low literacy levels. Implementing future motivational interviewing training programs with more valid outcome measures could inform future studies and employers of this population.