In this paper we analyse critically early design stages software in its capacity of coping with contextual data at large (i.e. representing cultural, aesthetical context, etc.). We identified 5 categories of early stages software: geometry based graphic editors, evaluation architectural software, generative and shape-grammar based systems, evolutionary systems and other systems. Calling the object under creation during of the early stages a CAD conceptual model, we will investigate to what extend this software allows the architect to experience and represent the context in which a design is situated. Especially we will focus on its capacity to allow interaction, playful interaction on our way to the design. Designers, and particularly architects, interact with the local context similarly to interacting in a game: the context influences the usersi decisions, surprises them and causes permanent changes to their ways of thinking. On the other hand, architects permanently shape and reshape the context, and reduce the context to a protean point of reference. Such behaviour characterises creative thinking that is crucial for the early stage of design. The investigation led us to the conclusions that the effective interactivity with the context needs simple rules, a plain interface and data reduced as simple as possible, especially when interaction with the context is performed during the early stages of a design process. The findings can be used in organising computer environments for early-stage design.