Leaders pressured to “innovate or die” and “fail fast” in this new always-agile, everything-digital business environment have constantly been asked “Why not?” Sometimes, the question is a challenge to set ways of working; other times, it is a result of practiced work-arounds for existing technology. But with new risks from new business models and digital services shifting how companies innovate, business leaders are rightly asking “Why?” before mapping compelling arguments against the risk policies associated with a proposed investment. This shift to asking “Why?”, after a decade of being worked around or brought into business discussions after the fact, suggests rising influence for experts in business continuity, public policy regulations, and consumer sentiment around data, data protection and the proper use of data in the digital era. This shift has been particularly acute for digital native firms whose risk of exposure was not as great when launching as compared to transforming companies that have more experience with and exposure to the regulatory landscape, as well as experience managing and securing data. As transforming companies increasingly view data as an asset, not just a storage headache or a risk, leaders will find themselves asking the next question: How fast? — How fast can we transform within our risk parameters, within the bounds better understood now that the innovative and compliance mindsets are in sync?