This study investigated key principal leadership skills associated with socially proactive school environments and examined the relationship between School-Wide Positive Behavior Support (SWPBS) implementation and increased evidence of those skills. Findings indicated the following: (a) certified staff members and principals from all schools rated the importance of each of the 31 skills as high; (b) principals in SWPBS schools received significantly higher ratings associated with behavior management effectiveness; and (c) principals from SWPBS and non-PBS schools received relatively equivalent ratings in regard to transformational and managerial skills. SWPBS-certified staff respondents indicated statistically significantly greater rates of job satisfaction than did those in non-PBS schools. Implications for future research are discussed. (Contains 3 tables.)