Despite the potential of problem posing to improve student mathematical performance, the integration of problem posing in the mathematics classroom has been hampered by insufficient problem-posing activities in school textbooks. In this paper, I illustrate how teachers can naturally build a repertoire in problem posing by designing questions that relate to a textbook problem and address teaching, learning, and developmental goals of the lesson. At the focus of the paper is a strategy for posing five categories of questions that are easier, same, similar, more difficult, or different, relevant to a given textbook problem. The five categories can be easily interpreted by both teachers and students as they can align them to their own level of understanding. Teachers can use some or all of these problem-posing categories to enrich their usual classroom practices.