Heavy reliance of teachers on questions that are aimed to recall the information memorized tends to suppress students' thinking and frame it within a textbook content. To break this practice there is a need to develop teachers' understanding of questions that will help students think beyond the content of textbook. This study was aimed to understand the practice of myself, as a teacher educator, in facilitating the development of teachers' knowledge, skills and dispositions to ask High Order Questions (HOQs) questions that can help students to not only comprehend information, but also to analyze, synthesize and evaluate it. It is believed that sustained practice of Higher Order Questioning (HOQ) could scaffold the development of students' critical thinking, which is necessary in preparation of informed, cognizant and critical citizens for open, free and democratic society. The findings of the study reveal that if sufficient time is invested in development of teachers' understanding of HOQ, the practice of HOQ will be more effective and sustainable. Since the approach used in conducting this study was action research and the time allocated for the study was not sufficient, it was not possible to see the practice of the developed understanding of HOQ in classes.