Our ability to improve decision making in software development hinges on understanding how decisions are made, and which approaches to decision making are better than others. However, as of yet there are few studies examining how software developers make decisions in software design, especially studies that place agile approaches in the context of decision making. In this paper, we present results of a multi-case study of design decision making in three software organizations of varying levels of agility. We show an agile organization produced a culture that supported communication and debate about alternatives to design decision more than 2 organizations of lesser agility.