Few transition studies have involved training supervisors on interacting and relaying feedback to individuals with intellectual disability during vocational training. We used a multiple baseline across participants design to examine the efficacy of an adaptive check-in/check-out (CICO) intervention for increasing the rate of performance feedback statements given by a supervisor to an intern with an intellectual disability during vocational training. The CICO intervention was effective at increasing the rate of performance feedback statements given by each supervisor. We recommend research and practice focused on training supervisors to use the CICO intervention to assist in helping foster natural job supports.