The authors describe a journey of self-study during which one author shifted from traditional, teacher-driven approaches to a more problem-based inquiry approach to teaching mathematics. He videotaped a series of lessons taught to sixth-grade students over a semester and analyzed his teaching during discussions with his mentor at the university. The shared analysis helped him learn to involve his students more directly in their own learning. A major lesson learned was that understanding the potential value of a problem-solving approach to teaching mathematics does not guarantee corresponding changes in the classroom. Two vital elements of lesson development emerged as focal points for self-study. After first learning how to prepare worthwhile mathematical tasks, the teacher also learned the importance of implementing effective questioning strategies to help students think more deeply about the mathematics they were learning.