Today’s leaders are racing to reconfigure their organi­zations to be more adaptive and competitive. However, when looking for guidance on how to do that, they will discover two competing schools of thought in the Agile community: “First fix the culture” and “First fix the org structure.” In reality, this debate between a culture-first or structure-first strategy is misguided. Leaders need to encourage a conversation that incorporates both perspectives. Through this two-sided conversation, they can guide an organizational transition that is both meaningful and sustainable.