Most observers who have written about holacracy and other forms of self-management take extreme positions, either celebrating these “bossless,” “flat” work environments for fostering flexibility and engagement or denouncing them as naive experiments that ignore how things really get done. To gain a more accurate, balanced perspective, the authors—drawing on examples from Zappos, Morning Star, and other companies—examine why these structures have evolved and how they operate, both in the trenches and at the level of enterprise strategy and policy. Self-organization models typically share three characteristics: Teams are the structure. Within them, individual “roles” are collectively defined and assigned to accomplish the work. Teams design and govern themselves, while nested within a larger structure. Leadership is contextual. It’s distributed among roles, not individuals, and responsibilities shift according to fit and as the work changes. Adopting self-management wholesale—using it to determine what should be done, who should do it, and how people will be rewarded across an entire enterprise—is hard, uncertain work, and the authors argue that in many environments it won’t pay off. But their research and experience also suggest that elements of self-organization can be valuable tools for companies of all kinds, and they look at circumstances where it makes more sense to blend the new approaches with traditional models.