The research reported in this article formed part of an internationally funded project about the empowerment of Information Technology (IT) teachers in economically deprived rural schools in the North-West and KwaZulu-Natal provinces in South Africa. The current paper focused on the use of self-directed metacognitive (SDM) questioning in a pair programming context. The study sample consisted of five IT teachers and 99 Grade 10 IT learners at five schools. The teachers were trained to implement pair programming and to guide learners in the application of metacognitive regulation while doing pair programming. The learners used SDM questions during their subsequent pair programming tasks. Data-gathering was done through interviews with the teachers regarding their views on the use of the SDM questions, and the learners' journals with their views on how they experienced the SDM questions to direct their thinking during execution of pair programming tasks. The results indicated that the teachers viewed the implementation of the SDM question difficult and time-consuming, and that they experienced the learners to be either reluctant or unwilling to engage in SDM questioning. However, the results of the learners' journals indicated that the learners experienced the SDM questions to be helpful in directing their thinking during pair programming tasks.