n this study we investigate how teams analyze tradespace early on in the life cycle of projects. Specifically we observe how levels of engagement – based on active involvement in project tradespace exploration – influences the quality of project plans and readiness of teams for performance. We hypothesize that shared awareness of project dynamics among project stakeholders increases through simulation-based training during the planning process. To test the hypothesis and the conditions of such increase, we conducted a comparative study comprising controlled experiments at Technion and MIT, using two Project Management planning approaches: (1) The traditional Gantt chart development supported by critical path analysis and (2) role-based project simulation. This study of a small test population shows a difference in the increase of shared understanding among project stakeholders based on the planning method followed. These initial results suggest that a team's method for tradespace exploration matters, influencing shared awareness early on in the project life cycle. In future experiments we hope to further test this finding and continue to investigate correlation with readiness for improved decision making throughout the project life cycle.