In July 2005, the Little Rock, Arkansas, school district implemented a new policy to reorganize its management structure in order to create a more efficient bureaucracy. Using Richard Matland’s ambiguity-conflict model of policy implementation, the authors examine the implementation of this school reorganization policy. Interviews and surveys were conducted with the superintendent and his executive assistants, school principals, teachers, and staff. In line with Matland’s model, the findings suggest that successful implementation is directly related to the policy characteristics of ambiguity and conflict. However, the authors point to the importance of recognizing particular characteristics for different groups of stakeholders within the policy implementation process. Discrepancies among groups of policy actors in the degree of policy ambiguity and policy conflict lead to strikingly different implementation strategies.