The collaborative efforts of families, educators, and policy makers have merged vocational training with special education services for students with disabilities. The Individuals with Disabilities Education Act of 2004 introduced mandates for schools to provide transition services for students with disabilities based on three areas of need: a) education, b) employment, and independent living. This legislation has led to more work-based learning programs that meet the postsecondary needs for students with disabilities. Despite this increase in work-based learning programs many students with disabilities are still unable to make successful transitions into postsecondary outcomes. Using a mixed method design, this study examined the impact of a Job Experience Training (JET) program on the executive functioning skills of seven young men (15 to 18 years of age) over the course of seven weeks at an assisted living facility. Results of the teacher evaluations showed the students were capable of completing tasks, making individual goals, and increasing executive functioning skills while participating in the JET program. Conversely, the results from the parent and student assessments showed little to no change in executive functioning skills once the participants were outside the context of the assisted living facility. Future research is encouraged to examine a longitudinal study across multiple job sites that evaluates and measures the students’ ability to transfer executive functioning skills to other contexts and further investigate mentoring as the core teaching strategy of a JET program.