Individuals with an intellectual or developmental disability experience poorer postsecondary outcomes compared to same-age peers. Research identified barriers to employment include soft skills. This single case study examined the application of self-evaluation to employable soft skill behaviors for three individuals with an intellectual or developmental disability. Technology was integrated into the evaluation process to increase efficiency. All participants worked in a Project SEARCH site for the majority of their school day fully immersed in an authentic work experience program. This study explored the effect of self-evaluation on a self-selected target employable soft skill behavior, how closely student self-evaluation scores matched with job coach evaluation scores, and the potential relation to self-determination. Data collection were halted due to the COVID-19 pandemic; however, results demonstrated self-evaluation may be a promising practice applied to employable soft skills. As students participated in the self-evaluation intervention, their target behaviors increased, and scores began to trend similarly to the job coach evaluation scores. Social validity evaluation showed key stakeholders felt the intervention was useful, easy to implement, and an important skill to learn to improve self-determined behaviors. Findings from this study provide practitioners with a practical, easy to incorporate strategy within an authentic work experience program.