As the information profession addresses ways to un-silo assets and operations within our organizations, information managers are realizing the critical need to engage collaboratively to solve problems and make more strategic decisions. The authors will discuss a case study that addresses this need and exemplifies a new model of collaboration. Through examining a library digital asset system migration implemented via a team approach, the presenters will share several empowering possibilities that are created when information technologists, metadata experts, and managerial professionals learn to work together as decision-makers. The team experienced challenges; and these challenges will be described as scenarios with multiple perspectives, challenges and approaches. Using visualizations, the presenters will illustrate the spectrum of organizational perspectives and associated assumptions and delve into common fears and perceived threats when negotiating resource commitments. With these themes exposed, the presenters will offer recommendations for navigating each scenario with a focus on improved and inclusive communication. Recommendations will focus on techniques to encourage healthy debate; particularly in regard to respectful assertion of preferences, effective translation of complex concepts, and streamlined decision-making in flat hierarchies like committee and team structures.