Drama-based practices have been increasingly adopted in design as it adds adimension to one’s understanding of the subject matter by featuring sensory, cognitive, spatial-physical experience and interaction, which goes beyond the static methods we are already familiar with in design. Although past studies have already argued for drama’s role in design, most discuss the value of the staged performance and its elements, rather than the process in its entirety. However, we seethe value in the dialogic, explorative and convergent qualities of drama that could bring much potential for enabling changes in understanding, especially pertaining to complex and ambiguous issues. As design evolves to deal with increasingly open and interconnected societal problems that often come with an open-ended brief involving complex stakeholder networks, designers need to be equipped with the right skillsets to navigate complexity and ambiguity. In our attempt to teach an introduction to system-level thinking in design education, we developed ‘Stakeholder Improv-Play’— a method that enables design students to approach the networked complexities of project briefs in diverse operating contexts, through a combination of improvisation and role-play. In this paper, we discuss how this method has been developed and applied, with borrowed elements from existing drama-based techniques that have been employed in design practices. We describe how the method can be adopted in a design education setting, and the changes in students’ levels of understanding that we have observed through our case stud