Post-school employment outcomes for individuals with disabilities continue to be inadequate when compared to their peers without disabilities (Newman et al., 2011). One barrier to employment for individuals with disabilities is a lack of employment "soft skills" (Riesen, Morgan, Schutlz, & Kupferman, 2014), such as punctuality and work completion. This study investigated the effects of UPGRADE Your Performance on soft skills of secondary students with disabilities at both in-school and community-based job sites. UPGRADE Your Performance instruction included self-monitoring, goal setting, self-graphing, and technology-aided instruction. Results demonstrated all students improved in a self-selected soft skill area, made gains in their overall performance, were able to self-monitor their own performance using a handheld device, and generalized their skills to a second setting. Implications for practice and suggestions for future research are included.