Is it possible for principals/heads to be effective educational leaders? In this study, we compared the work of principals/heads in two policy contexts. In Policy Context 1, standards for student performance were common and well-established, and authority was devolved to the school level for reshaping the school to meet those standards. In contrast, Policy Context 2 involved attention to more locally defined standards, and authority was more rule-driven rather than directed by local self-management. Policy Context 1 provided several advantages for educational leaders. Principals/heads were able to use the formal leadership structure of the school and to be more focused on actually achieving student results as measured against standards. In contrast, principals in Policy Context 2 often had to spend considerable personal energy helping the school define its purpose/mission, and could not hold the collaborative focus tightly on a specific set of student standards or results. Implications for job structuring, principal development, and connections between policy and practice are discussed.