This article is a retrospective analysis of successful planning processes implemented in an urban school district in the Northeast United States to improve student behavior by incorporating positive behavior activities and strategies as well as infusing more specific character education into the curriculum. The results after three years of planning, implementing, and evaluating the program funded via a federal grant have been impressive. The planning and implementation approaches employed by the district for this program are consistent with those key "high-touch" approaches advocated by contemporary educational researchers and categorized in the planning literature as "managing in the effective change zone". Thus, this paper provides a case study of managing change in the "effective change zone" to promote meaningful and sustaining results.