Collingwood’s logic of question and answer directly challenges the traditional logic’s assumption that there exist autonomous units of thought. What his new logic proposes is to reconfigure this notion of autonomy within the purview of a question. This means that statements or propositions are to be comprehended as answers to postulated questions. As an effect, a statement only fills up one side of the coin. The question, being intimately connected with the answer, forms and constitutes the other side. If the logic of question and answer is used in education, our hope is to introduce students and teachers to a new habit of thinking: a heightened sensibility of the role of questions in thinking, education and comprehension. When this brand of logic is understood and applied to teaching, students and teachers will look at statements and questions in a different way. On the one hand, statements shall be seen and analysed together with the questions. Questions, on the other hand, shall be carefully looked into and comprehended within the contexts of answers. With this new logic, we may assert that Collingwood’s logic of question and answer can make a two-fold contribution to (a philosophy of) education: (1) Questions can be reckoned as answers in themselves, (2) Answers are to be comprehended within the compass or ambit of a question.