Teacher evaluation is a major reform initiative in public education's high accountability policy environment. Principals' effective implementation of this high-stakes reform is challenged by time management, policy coherence, communication with teachers, district support, and staff development imperatives. Effective implementation requires moving beyond time and management concerns towards collaborative leadership with supervisors. Although teacher evaluation policies are often state initiated, local level superintendents and district leaders must understand principals' challenges to provide useful guidance and support. Based on a three-year study of a southeastern state's Race to the Top driven implementation of redesigned teacher evaluation policies, this article examines principals' concerns and need for support plus superintendent strategies for addressing gaps that state and federal policymakers may leave during such mandated reform. The Stages of Concern framework from the Concerns-Based Adoption Model (CBAM) was used to examine principals' concerns and superintendents' support. Lessons learned and implications for superintendents are described.