In this chapter we explore the relationship between developing a descriptive understanding of human behavior and designing artifacts which ostensibly support the activities described. Although there is growing recognition that an understanding of users’ current work practices would be useful in the design of new technologies, the debate about what it would mean to acquire such understanding and to link it with design is only beginning. What are the implications of developing ways of representing the views and activities of communities of practice outside one’s own such that the knowledge would be useful in design?