A primary to secondary school transition still exists for students in Queensland schools, despite a policy focus on the middle phase of learning since 2002. The Queensland State School Action Plan (2003) focuses on the unique characteristics of new millennial adolescent learners and the effects of (potentially) negative schooling experiences during years 4 to 9, and challenges teachers to plan for a greater degree of alignment between curriculum, pedagogy and assessment practices, particularly during the transition from year 7 to 8. This paper reports on case study data from a teacher exchange project designed to help primary and secondary teachers better understand issues in the opposite schooling sector. The teachers reflected on what they had expected to see in the other sector’s learning site and what they actually saw when they observed teaching on ‘the other side of the fence’. Their observations focused on teacher planning, curriculum, pedagogy, teacher/student relationships and student behaviour. The study reveals that teachers from each sector understood little about the ‘other’ educational sector, and in most instances, the realities did not match the expectations. The study confirms the value of teacher exchange and work-shadow approaches to cross-sectoral understandings of middle schooling issues.