The principles articulated in the Agile Manifesto make a lot of sense to the software craftsman who dreams in code. They can, however, be quite puzzling to executives who consider Agile software in the context of their company’s established norms and patterns. Assumptions embedded in a business design with respect to customer relationship, competitive differentiation and value capture are not necessarily aligned with the principles advocated in the manifesto. Moreover, the core culture of a corporation might not be hospitable to Agile principles. Corporate culture basically specifies “how we do things around here in order to succeed.” Agile Principles challenge these norms. The path an Agile roll-out should follow depends on the core culture of the corporation: control, competence, collaboration or cultivation. Irrespective of the specific culture, the Agile roll-out invariably tests cultural integration, wholeness and balance. In particular, it exposes inconsistencies between approach with customers versus approach toward other constituents of the corporation such as partners and employees. Consequently, corporate reactions to Agile often express the disappointment of an organization when it is forced to take a good look in the mirror. Grass roots Agile initiatives can propel a company a long way. However, the creation and capture of long-term value is invariably linked to successful business design and coherent corporate culture. To succeed on a large scale, bottom-up Agile initiative must be complemented by top-down commitment to learn, change and keep a living company. It is the combination of the two, the willingness to apply Agile practices in an indivisible manner that will fulfill the premise of the manifesto.