Our assessment research suggests that quantitative business courses that rely primarily on algorithmic problem solving may not produce the deep learning required for addressing real-world business problems. This article illustrates a strategy, supported by recent learning theory, for promoting deep learning by moving students gradually from “well-structured” algorithmic problems with single correct answers to “ill-structured” real-world business problems that may have multiple correct answers and require an argument addressed to a specific audience. We show how these scaffolded communication assignments promote deep learning, and suggest ways that interested faculty can adapt the assignments to their own courses.