This article will argue that diverse national, regional and local contexts leave different rooms for manoeuvre for school principals. The social technologies applied by the authorities (like accountability systems) can be 'tight' or 'loose' and so leave little or much room for principals' interpretations of what a good school is and what successful school principalship is. Thus it is important for their choice of forms of influence in exercising leadership. We will outline the relations between the state, local authorities and schools in each of eight countries participating in the International Successful School Principal Project (ISSPP): the USA, UK, Canada, Australia, China, Norway, Sweden and Denmark, based on previosly published case studies. We want to obtain a deeper and more nuanced understanding of the social technologies used and the room for interpretation of the purposes and objectives left to the schools. Principals choose the forms of influence they can exercise when setting directions for the school. The arguments on which principals base their decisions are also diverse, but heavily flavoured by the contexts in which the schools function. Comparing education and educational leadership and the values and practices of school principals is a contested enterprise because the contexts in which the values are constructed and practice developed is often forgotten. In posing the questions from above and below the level of principal, we try to take account of the findings from many leadership studies, which indicate that educational leadership and its successes are highly contextually dependent even within educational systems.