This action research report follows the journey of four elementary school teachers as they learn to define and ask "deeper" or meaningful mathematical questions in their teachings. It chronicles the way that teaching through problem solving and developing criteria for questioning increased the percentage of "deeper" questions being asked and answered by their students. Study results highlight the importance of student involvement in sorting and defining questioning criteria. Finally, it outlines key teacher and student learnings related to questioning in mathematics and recommends next steps for implementation.