Agility prepares us for our turbulent future. But how do we achieve enterprise agility in light of the magnitude of that turbulence and the overwhelming number of failed transformation initiatives? In this Amplify Update, we suggest that growing agile-adaptive leaders who are adventurous, inspiring, and, of course, adaptive is critical to success. We then seek to validate that assumption by listening to the voice of a former CEO of IBM. By understanding this brand of leadership, digital and Agile transformations can be more successful. However, lurking in the shadows of even the best agile-adaptive leaders are the formidable obstacles of rigid cultures, financial myopia, and performance hacking.