In this study, we extend overqualification research to employees' social context of workgroup membership. Drawing upon social comparison theory and integrating with social exchange theory, we contend that employees' relative overqualification (ROQ, defined as individual overqualification relative to other group members' overqualification perceptions) is associated with their relative standing with their leader (measured as LMXSC, leader–member exchange social comparison), which in turn relates to employees' organizational citizenship behaviors (OCB). Furthermore, we assert that workgroup structural attributes and individual values (leader span of control and power distance orientation) influence the ROQ–LMXSC–OCB relationship. Multilevel modeling using data from 243 employees nested in 36 workgroups suggested patterns of moderated mediation where leader span of control and employee power distance orientation moderate the indirect link between ROQ and OCB through LMXSC. That is, the indirect relationship between ROQ and OCB is stronger in workgroups with a narrow leader span of control and for employees high in power distance orientation. Implications and directions for meso- and group-level research are discussed.