Transition-age students with extensive support needs often participate in community-based work experiences (CBWEs) in preparation for competitive, integrated employment. CBWEs help students gain exposure to different careers, acquire employment skills, and generalize skills learned at school to community settings. Despite their benefits, CBWEs have been known to create scheduling conflicts and decrease school-based instructional time for special educators who must address student goals in academic and functional skill areas. Identifying authentic opportunities to address Individualized Education Program (IEP) goals during students’ CBWEs is one solution that can assist special educators who are faced with such challenges. An existing tool, commonly known as an IEP Matrix, may be particularly useful in helping teachers navigate this process. In this article, we describe how to develop an IEP matrix and assess the feasibility of instruction on IEP goals within CBWEs. We also provide recommendations to consider when identifying and evaluating instructional opportunities.