Ground-breaking technologies are developed for use across a broad range of domains such as manufacturing, military, homeland security and automotive industries. These advanced technologies often include intelligent systems or robotic elements. Evaluations are a critical step in the development of these advanced systems. Evaluation events inform the technology developers of specific needs for enhancement, capture end-user feedback, and verify the extent of the technology's functions. Test exercises are an opportunity to showcase the technology's current abilities and limitations and provide data for future test efforts. The objective of this research is to develop the Multi-Relationship Evaluation Design (MRED) methodology, an interactive test plan blueprint generator. MRED collects multiple inputs, processes them interactively with a test designer and outputs evaluation blueprints, specifying key test-plan characteristics. Drawing from the Systems Engineering Paradigm, MRED models a process that had not been modeled before. The MRED model is consistent with the experience of evaluation designers. This method also captures and handles stakeholder preferences so that they can be accommodated in a meaningful way. The result is the MRED methodology that combines practical evaluation design experience with mathematical methods proven in the literature.