Agile transformations are complicated endeavors, especially for large enterprises trying to keep pace with today’s fluid digital marketplace. For change to be sustainable, it cannot be led in a vacuum. Both the right and left hand sides of delivery much adapt accordingly. Most practitioners have only led agile transformations from one side of the house: IT or Business. But a house divided cannot stand. This talk offers revelations from one person who has led transformations as both a product owner and scrum master. Each side faces different challenges, but one commonality remains: by shifting to a generative mindset, they can succeed together.