Planning, like all dimensions of education, is a political activity. As the space and process in which teachers make big decisions about curriculum, pedagogy and purpose, choosing what to teach, how to teach it and why requires teachers to engage with their knowledge of the children they teach, their knowledge of educational policies and theories, alongside geographical knowledge, ideas, values and methods. Put another way, planning is much more than just the technical act of writing a lesson plan or scheme of work. In this chapter, we write together as two university-based tutors who work in Initial Teacher Education and three school-based mentors who also work as full-time geography teachers, to examine the theory and practice of planning in geography education. Following hooks, writing in 1994, we then engage in a dialogic conversation to critically consider our experiences of, and perspectives on, planning with beginning teachers. Our examination highlights the complexities and challenges of the mentor’s role in supporting beginning teachers to think critically about their planning, and the value of partnership between schools and universities in developing well-informed and empowered beginning geography teachers.