Social skills are of key importance in everyday and work life. However, the way in which they are typically assessed via self-report questionnaires has one potential downside; self-reports assess individuals’ global self-concepts, which do not necessarily reflect individuals’ actual social behaviors. In this research, we aimed to investigate how self-concepts assessed via questionnaires relate to skill expression assessed via behavioral observations after short interpersonal simulations. For this, we used an alternative behavior-based skill assessment approach designed to capture expressions of predefined social skills. Self- and observer ratings were collected to assess three different social skills: agency (i.e., getting ahead in social situations), communion (i.e., getting along in social situations), and interpersonal resilience (i.e., staying calm in social situations). We explored how these skills were related to self-concepts by differentiating between a classic personality measure (i.e., Big Five Inventory 2; BFI-2) and a novel skill questionnaire (i.e., Behavioral, Emotional, and Social Skills Inventory; BESSI). The results (N = 137) showed that both personality and skill self-concepts predicted self-rated skill expression, with the BESSI showing incremental validity. For both personality and skills self-concepts, the relationships with observer-rated skill expression were significant for agency but not for communion or interpersonal resilience. We discuss these results and highlight the theoretical and practical importance of differentiating between skill self-concepts and actual skill expression.