Distinctive school contexts pose a challenge for professional learning for school leaders but this distinctiveness does not mean professional learning has to become entirely individualised. Schools with clusters of common contextual characteristics can provide a middle ground for professional learning between wholly generic versions of ‘good practice’ and wholly individualised ones. Yet because professional learning for school leadership has often been generic in its approach, these contextualised examples are generally not to the fore. It is often hard to work out which practices would be most appropriate for schools in particular social settings. This article describes the ‘School leadership in context’ courses, a New Zealand initiative that approached this problem by providing relatively targeted professional learning. The courses collected together the principals of small rural schools in particular geographic areas with the intention to provide a forum for discussion centred on the needs of ‘like’ schools facing a number of similar issues and problems, getting away from the one-size-fits-all approach that so often dominates professional learning offerings in New Zealand and elsewhere. The article discusses the political background to this professional learning and goes into considerations in providing the courses such as which groupings of school leaders to invite, and what the courses covered. The article also discusses some enduring challenges in providing professional learning centred on school context highlighted by the courses.