The architect and designer Charles Eames is quoted as saying, “The role of the designer is that of a very good thoughtful host anticipating the needs of his guests.” The challenge for designers today is to base that anticipation on nuances, and to look beyond the surface of behavior to better understand the root causes. And as the relationship between designer and user becomes more integrated and interactive, we have better and more sophisticated and more creative methods by which to engage in this relationship. Throughout this section, the argument about usability is to attempt to look beyond the surface behaviors of people to and seek out a deeper understanding of the motivations that drive these behaviors and to critically reflect on the impact that design has on how users interact with it, and might adapt and change, for better AND for worse. For designers, this means expanding the methods by which we are gathering information and interacting with existing and future users of our projects. It also means remaining nimble throughout the research and design process–not using research only as a means by which to confirm our assumptions, but being open to the discovery of new ideas that might contradict what we thought we knew about people, their beliefs, desires, and wants and needs. The two case studies in this chapter seek to unpack how comparative design research gain garners new insights into design outcomes. The students at Maine College of Art, under the leadership of Brooke Chornyak, raised critical questions about who was being designed for, and how the collective wisdom of users could be used to create a system of checks and balances for others. A series of examples from the Project for Public Spaces and Google showcases how users are pivotal parts of the design research process through more incremental approaches.