As faculty members in an instructional design and technology (IDT) program, we wanted to help our graduate students better understand and experience how designers design in the real world. We aimed to design a reflective and collaborative learning environment where we sparked students to engage in reflection, ideation, and the iterative process of problem-solving. For an assignment in a graduate IDT class, we piloted using Cacoo, an online diagramming and mapping tool, to provide and simulate an authentic learning environment to create external representations. For a distance education time machine design assignment, our pilot focused on the ways in which an external representation environment was used to stimulate students' reflective conversations with design drafts. We share our pilot story by presenting the literature that grounded our pilot, a description of the participants and design assignment, our choice to use Cacoo, the design process, the design assessments, and the pilot's significance and next steps.