The way in which environmental designers design neighborhood spaces has a role to play in the quality of outdoor spaces that shapes and directs daily outdoor social activities as well as creates a bridge between individuals and the local community. The high quality design of outdoor spaces is fundamental in fostering social cohesion among users/residents in order to produce a healthy social atmosphere, whereas a decline in the quality of outdoor spaces can contribute to antisocial behavior. Today, In Jeddah City, Saudi Arabia, in many cases of new neighborhoods, the outdoor space has become abandoned, and empty, or is avoided. Within this setting, these spaces do not provide opportunities for families with their children to gather and play, to sit and socialize with neighbors, to gather in outdoor activities, to walk to the mosque or school, or to do their daily grocery shopping without being threatened by dangerous car traffic. Moreover, even if users and residents experience problems in their neighborhood, and have their own needs and visions to solve the problem, they do not have the experience to mentally visualize and resolve these problems. Through this qualitative research, the researcher proposes a new approach in incorporating users' imagination in the ideation process of design in order to examine to extend the current normative theory through the development of a more "collaborative ideation process."In this new collaborative process, the representation of ideas becomes more iterative and knowledge exchange between researcher and users becomes more seamless. Through incorporating the researcher's sketching skills as a process of "collaborative-sketching," possible ideas and solutions are explored that are responsive to the needs and desires of users. Using a number of photographs of an outdoor residential space as an example, the objective of this study is to examine the use of collaborative sketching as a way of taping into users' imagination as a rich source of their needs and desires to empower the design process. The findings showed that applying a collaborative sketching process in the early ideation stage of design can result in a rich exchange between designers and user, enabling the designer to have a better and more realistic understanding of needs and desires from the perspective of the user. Through this collaborative-sketching process, the users were continuously, iteratively, and instantly stimulated to not only to narrate their needs and desires, but to visually provide realistic and specific details about the social activities and physical elements including their affordance, rationale of using, value of use, and how social interactions might occur within the different settings. / Ph. D.