Successful project management requires continuous communication aligning the expectations between project stakeholders and the project team. Expectations include both product expectations (how the product will look, feel, and perform) and programmatic expectations (timelines, deliverables, expenditure of project resources). In order to make the most effective use of project resources throughout the life of the project, a process or tool for quickly aligning expectations as closely as possible should be employed early on in the project. Project management literature is lacking in tools for aligning expectations, and solutions and best practices need to be determined since the current best option is hiring experienced project managers and hoping they can communicate successfully. This paper lays out the quantitative statistical methods that are needed to evaluate the effectiveness of potential expectations alignment tools in order to determine best practices. Engineering capstone students lack the industry experience aligning programmatic expectations that a good project manager would have. Curriculum may not be addressing the alignment of programmatic expectations, leaving students with blind spots that can lead even the brightest of student teams to fail. Failure to properly align expectations and achieve project goals can then lead to ruined relationships and damage a program's reputation. Using the methodology we propose, we determined that students at Brigham Young University and the United States Air Force Academy have a statistically significant misalignment regarding two major programmatic expectations: design deliverables to be created as part of the project, and the desired technology readiness level the project needed to achieve. It was also determined that these students have a statistically significant bias towards overestimating the importance their sponsors put on creating prototypes. The alignment tool we tested and the alignment measurement methodology we propose provide a groundwork for future development and testing of tools and best practices for quickly aligning design teams' expectations with their stakeholders.