One of the things I find most attractive about this conference is the intentional link or connection of Digital Transformation to Whole System Change Leadership. Digital Transformation is more than one strategic priority or a special C-Suite project. Successful Digital Transformation requires fundamental changes not just in employee behaviour, but in the surrounding workplace climate and culture. Leading such system-wide transformations has not been particularly successful over the past few decades. This presentation will introduce a relatively new approach to leading positive change at the whole-system level, called Appreciative Inquiry. This type of “AI” was invented here at the Weatherhead School. It is a strength-based approach to organization transformation that has proven to pull or attract stakeholders to engage in designing and owning positive changes, vs. being pushed or forced into change. This session will highlight several myths that dominate our most popular, legacy theories of change management and illustrate how AI, as a strength-based theory and method, overcomes the limitations of past approaches to leading successful organizational change and offers promise for more successful digital transformation of whole systems.