Amid the enthusiasm generated by the success of agile approaches to software development in recent years, we have begun to extrapolate the principles of agile methodologies to propose innovative new ways of managing entire businesses, such as “self-reflective fractal organizations.” However, it is important to resist the tendency toward an attitude that managers have more to learn from us than we do from them. Such an attitude is based on the assumption of a direct and automatic link between agile development and business value creation that is often more imaginary than real, and certainly harder for them to recognize than us. Even a perfectly organized, successful agile project may fail to deliver any business value at all; even more often, we are unable even to judge whether any business value has been created. The potential of agile approaches to contribute to value creation is large, but only if we recognize that we must reach beyond them to study and learn from the best managers. This starts with an appreciation of how difficult (and rare) it is to create a sustainable competitive advantage with IT investment. Some lessons from top management can help us understand the sources of competitive advantage and how we can help our customers in their search for that elusive business value. In so doing, we enable ourselves to create better business cases for managers to invest in software development and we sharpen our own focus on what software development will create the most value for the business.