This paper reports findings from a formative design experiment during which the practical problem of how to support 31 preservice teachers as they approximated planning for ambitious literacy instruction was examined. Collaborative planning conversations between the PSTs and a teacher educator were analyzed. Discourse analysis revealed a macrostructure of anticipatory reflection that included (1) describing the literacy practices of the child (2) determining the learning goal for the child (3) planning for interaction with the child and (4) planning for lesson closure and transfer. Specific language interactions that supported anticipatory reflection are detailed and A Framework for Facilitating Collaborative Planning Conversations along with a Decision-Making Tool for Planning is offered.