In this chapter, the authors identify lessons about cross-disciplinary practice from their experience in the Toolbox Dialogue Initiative (TDI). These include the rich variety of ways failure can manifest in projects, the need to learn from failure, especially in the context of cross-disciplinary research and the need for project flexibility. The authors provide four case studies that mark important turning points in the development of the Toolbox dialogue method. These case studies focus on specific workshops that did not go as planned from the perspective of TDI. The first three workshops are from the Toolbox 1.0 period. The fourth is a more recent one that revealed inadequacies with the emerging Toolbox 2.0. The first three involved use of the Scientific Research Toolbox instrument, while the fourth involved use of an instrument designed for the partner group.