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Project management in a matrix organization is complex because project managers share the organization resources (budget and human), and cooperation between managers is critical for effective resource sharing. Therefore, training project managers in the matrix structure to work as a team is required. A simulator-based method to train managers to work as a team is presented. A project team builder (PTB) simulating a dynamic, stochastic multiproject environment was designed and implemented in a project management course for graduate students in systems engineering. Recording the learning history and having a debriefing mechanism were implemented as mechanisms to facilitate team learning. A total of 132 participants composed of graduate students, representing experienced managers, and undergraduate students as inexperienced managers, assigned into teams of three participants each, used the simulator in a multiuser multi-project mode. The findings indicate that for the initial learning phase and transfer to a different scenario, the three factors, history, debriefing, and experience, affected the performances. Furthermore, the interactions between the debriefing and history factors, between the experience and debriefing factors, and between the history and experience factors were all significant. Based on these findings, a new paradigm for a simulation-based team learning is presented.