The world of engineering design finds itself at a crossroads. The technical and scientifically rooted tools that propelled humankind into the modern age are now insufficient as evidenced by a growing number of failures to meet design expectations and to deliver value for users and society in general. In the empirical world, a growing consensus among many design practitioners has emerged that engineering design efforts are becoming too unmanageable and too complex for existing design management systems and tools. One of the key difficulties of engineering design is the coordination and management of the underlying collaboration processes. Development efforts that focus on the design of complex artefacts, such as a satellite or information system, commonly require the interaction of hundreds to thousands of different disciplines. What makes these efforts and the related collaboration processes complex from the perspective of many practitioners is the strong degree of interdependency between design decision-making occurring, often concurrently, across multiple designers who commonly reside in different organizational settings. Not only must a design account for and satisfice these dependencies, but it must remain also acceptable to all design participants. Design in effect represents a coevolution between the problem definition and solution, with a finalized design approach arising not from a repeatable series of mathematical optimizations but rather through the collective socio-technical design activities of a large collaboration of designers. Despite the importance of understanding design as a socio-technical decision-making entity, many of the existing design approaches ignore socio-technical issues and often view them as either too imprecise or too difficult to consider. This research provides a performance measurement framework to explore these factors by investigating design as a socio-technical complex adaptive collaborative process between the designer, artefact, and user (DAU). The research implements this framework through an agent-based model, the Complex Adaptive Performance Evaluation Method for Collaboration Design (C2D). This approach allows a design management analyst to generate insights about potential design strategies and mechanisms as they relate to design complexity by examining the simulated performance of a design collaboration as it explores theoretical design fitness landscapes with various degrees of ruggedness. / Ph. D.