This qualitative, collaborative action research study explored preschoolers’ learning of mathematical concepts as their teacher used productive questions as a key pedagogical strategy. The teacher’s use of productive questions was also investigated. One early childhood supervisor, a preschool teacher and eight 4-year old students from her class participated in this research. Data were collected through observations of teacher and students’ question-answer interactions, and semi-structured interviews with the teacher. The findings indicated that the use of productive questions increased the number of student responses that demonstrated higher order thinking, and although challenging for the teacher, allowed students to be actively involved and responsible for their own learning. One implication of the findings is that teachers need to be supported and guided when exploring new pedagogies (such as the use of productive questioning) to ensure proper implementation and to assist in overcoming challenges that will invariably arise.