This document describes the transition of Winnipeg Transit from an adversarial, top-down management structure to a collaborative work system through partnership with the Amalgamated Transit Union. It details how a crisis over a contentious contract led management to commit to collaboration. A working committee was formed with representatives from management, the union, and bus operators. Through focus groups, trust- and morale-building initiatives, and developing new systems collaboratively, the relationship and culture improved. Key successes included cost savings, improved employee surveys, and reduced grievances. While a proposed new scheduling system was initially rejected, the experience reinforced lessons about maintaining trust in the collaborative process.