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This chapter describes the change efforts and action research projects at a Dutch multinational which, over a period of 25 years, produced in one of its businesses a zigzag path toward collaborative leadership dynamics at the horizontal and vertical interfaces. The chapter also identifies the learning mechanisms that helped achieve this transformation. Changing the patterns at the vertical interfaces proved to be a most tricky, complex, and confusing operation. The data show that organizations need hierarchical interfaces between levels, but are hindered by the hierarchical leadership dynamics at these interfaces. The data furthermore show that competitive performance requires more than redesigning horizontal interfaces. A business can only respond with speed and flexibility to threats and opportunities in the external environment when the leadership dynamics at agility-critical vertical interfaces are also changed.