This chapter explores three broad principles of user-centered design methodologies, including participatory design, iteration, and usability considerations. We discuss characteristics of teachers as an important type of ITS end user, including barriers teachers face as users and their role in educational technology design. To exemplify key points, we draw upon our own experiences in developing an ITS for writing strategies (i.e., the Writing Pal). We conclude by offering a tentative design approach—the Design Implementation Framework (DIF)—that builds upon existing cyclical design methods but with some tailoring to ITS and educational technology contexts.