We all want to scale the benefits of Agile up from the team level to the wider organization. Our leaders pine for the holy grail of “enterprise agility.” Before beginning such a monumental endeavor, it is wise to take stock of the territory. Scaling a process may now be doable, but how do you scale leadership? Or culture? Leveraging learning from the field of Organization Development (OD), as well as Integral Theory, this session will walk you through the “how tos” of conducting a focused and comprehensive organization assessment. Using the Integral Agile Transformation Framework ™ from my book, *Coaching the Agile Enterprise*, we will cover topics ranging from why the concept of systems entry is critical to success, how different assessment modalities can be used effectively, what formal and informal methods exist, the importance of examining a full-range of topic areas, and the key qualities of the feedback meeting in engaging stakeholders and understanding the data.