The purpose of this grounded theory study was to understand and explain how training and work setting experiences influence readiness of professional school counselors for serving gang members in schools. A purposeful sample consisted of secondary school counselors (n = 5) and school leaders (n = 7) in a southeastern metropolitan school district. Blended themes from the counselors and leaders were: (a) professional development attitudes, (b) actual and potential roles when working with students in gangs, and (c) counselors’ collaborative role in discipline process. The Collaborative C.A.R.E. theory that emerged from the thematic analysis highlighted the absence of collaboration between school counselors and leaders. Specific findings identified reasons for the lack of collaboration and led to recommendations for practice and further research.