This chapter focuses on the causes and consequences of enhanced complexity of design activities by the social context. The eight design projects, which were used as stimulating material, were analysed towards the variables which contributed to the social context. All interviewees discussed collaboration between different stakeholders as one of the main ambiguous issues in the design process. In the paper the challenges of the three problems prevalent in most projects are analysed in further detail: unshared or contradictory goals between different stakeholders involved in the process, the need for crocc-disciplinary communication and the uniqueness of the projects. Finally, two concepts are presented and further detailed in how they may provide opportunities of influencing these complex social processes in a desired direction.