This paper presents the results of a case study carried out under the ISSPP in the Algarve, the most southerly region in Portugal, which is very diverse geographically and culturally, comprising areas that are quite distinct from each other in terms of development indicators: such as the more economically developed coast, compared with the underdeveloped rural areas. Each area has its unique set of problems. In this varied region, schools and their leaders have to find solutions to help pupils achieve success, and, through practices of creative, assertive leadership, face up to the problems created by circumstances. They do this in a number of ways, such as strengthening the role of intermediate leaders, sharing decision-making processes, encouraging the circulation of information and the creative, effective and innovative use of resources. The data were collected through interviews held with the head teachers of different schools, located in different contexts, which enable us to analyse methods and processes used by school leaders to respond to the challenges they face, in an exercise of leadership which is seen as a solution to the problems confronting schools and which, in this way, makes a clear contribution to pupils’ success at school.