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Research on the transition from school to work suggests that students entering the workplace struggle to adapt their writing and speaking to individual audiences. To address this problem, the article presents principles for using problem-based learning to design assignments that teach students to tailor communication to the needs of audiences. The approach focuses not on specific workplace documents but on the higher order workplace practice of effectively connecting documents and presentations to audience needs, and designing communication accordingly. A two-year study of capstone design courses suggests that the approach encourages students to explicitly consider audience needs when composing.