It is ironic, but perhaps not unexpected, that many organizations who want the benefits of using an Agile approach to deliver software use a waterfall approach to adopting Agile practices: they form plans, they set milestones, and they measure progress by how many teams they have engaged. Old habits die hard, but like most waterfall software projects, most waterfall-style Agile adoption efforts fail to produce the results desired. The problem is that to get the results they want, they have to change their culture and cultures are very hard to change. To paraphrase Peter Drucker, “culture eats Agile for breakfast.” Successful approaches are opportunistic and leverage the power of self-organization to achieve lasting change. This talk will share stories of success and failure and will talk about why different approaches succeed and fail.