The challenges inherent in developing a multifaceted problem and maintaining the teacher’s role as facilitator are exemplified in the authors’ case study of an Ontario sixth grade teacher who introduced a real-life premise for a follow-up unit on multiplication and percentages. Inviting her students to think of themselves as managers of a new hockey team, she asked them to solve a range of multifaceted problems, only to learn that they had almost no conception of either multiplication or percentages outside of the context of the traditional math unit.