Urban brownfield regeneration projects are complex operations that are not automatically sustainable. To facilitate the integration of sustainability issues in these projects, a recent research project led to the creation of an operational monitoring tool tested on case studies. Following this, we undertook interactions with the stakeholders of the case studies to confront the potential of the tool with the future end user’s point of view and the reality of the practice. This paper presents the method and results of these interactions. Essentially, it has been recognized that the tool could provide a valuable decision-making support throughout the transformation of urban brownfields into new sustainable neighborhoods. The inclusion of a monitoring tool into the management of these projects appears not only feasible, but realistic and desired.