In this paper I present a general outline of those parts of Gregory Bateson's work which appear relevant to building a questioning framework for appropriate analysis of interface design. A grounding in his fundamental philosophy is given first as a means to set the stage and become familiar with his approach to perceiving the environments in which we find ourselves. This is followed by a review of his theory of types of learning which shows how individuals gain knowledge through various levels of corrective strategies. From this body of Bateson's theory I draw forth a set of heuristics appropriate for critical analysis of interface design. Finally I use these heuristics on a particular case study to illicit both the strengths and weaknesses of the interface involved and those of the heuristics themselves.