Abstract: This paper presents research that aims to inform the development of computational tools that better support design exploration and idea transformation - key objectives in conceptual design. Analyses of experimental data from two fields - product design and architecture - suggest that the interactions of designers with their sketches can be formalised according to a finite number of generalised shape rules defined within a shape grammar. Such rules can provide a basis for the generation of alternative design concepts and they have informed the development of a prototype shape synthesis system that supports dynamic reinterpretation of shapes in design activity. The notion of 'sub-shapes' is introduced and the significance of these to perception, recognition and the development of emergent structures is discussed. The paper concludes with some speculation on how such a system might find application in a range of design fields.