Out-of-School-Time (OST) programs are increasingly recognized as a venue to actively engage children and youth in character development activities, but little guidance exists as to how to assess individual children and youth in OST environments for the sake of evaluating their character development. This research brief uses an illustrative case study to reflect upon the experience of selecting and completing a strength-based, multi- modal social-emotional / character assessment that used a direct assessment and a multiple informant behavior rating scale in an OST setting. Insights derived from the case study reveal opportunities and challenges associated with each assessment modality. This paper shares lessons learned with those conducting individual assessments in OST environments and with those seeking to improve our capacity to complete screening, formative, and summative assessments of social-emotional and character constructs in OST youth development programs to help children.