This study explores the relative value of Stafford Beer’s Team Syntegrity approach in determining the possible futures for the retail industry. The foresighter’s toolkit expands as multiple disciplines contribute to an evolving set of methodologies and practices. To date, scenario planning is most commonly associated with a standard matrix, based on two critical uncertainties, that is also used to evaluate strategic directions for organizations. This process, however, is sometimes criticized for its lack of complexity and integration of stakeholder knowledge. Fast moving or distressed economic sectors, such as retail, may learn more from foresight processes that are more participatory and agile, while maintaining complexity. Team Syntegrity, largely a strategic planning tool, may prove to be a beneficial alternative, as it integrates scenario and strategic planning purposes in its very design. This study compares Team Syntegrity and scenario building (the 2x2 matrix), sheds light on the turbulence within retail today, and explores possibilities for greater resilience tomorrow.