A primary to secondary school transition still exists for students in Queensland schools. Since 2002, the Queensland State government has implemented a raft of education and training reforms, including a Middle Phase of Learning State School Action Plan. The Action Plan recognizes the particular characteristics of new millennial adolescent learners and the effects of 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 during these transition years. This paper reports on case study data from twenty-six teachers (from five primary and two secondary schools) as they 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. It also confirms the value of teacher exchange and work-shadow approaches to cross-sectoral understandings of Middle Schooling issues.