Research into digital design environments has explored modelling, generating and testing design propositions. When considering the broader design literature, however, we notice that a significant contribution to design is absent, that of diagramming. In the realm of architectural theory discourse in the past few years, diagramming has been much discussed with many interpretations of the activity. This paper will demonstrate that the development of digital techniques can change dramatically our ability to conceptualise and produce generative diagrams as previously not possible. The paper will follow the work done at the in the Melbourne School of Design. We will demonstrate how students are introduced to diagramming techniques and shown how to formulate a concept, then a program generator and to test a final proposal. The paper will also demonstrate how digital techniques can dramatically change the way we conceptualise and approach design problems. In this repeated teaching technique, we illustrate how digital systems contribute to conceptual diagrams and this contributes to the larger theoretical debate on diagramming techniques by introducing digital perspectives. The paper will therefore contribute to discussion on the ways in which digital systems can be engaged in substantive architectural teaching beyond the rote application of proprietary software and representative approaches.