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New management approaches emerging in the discussion about work 4.0 are closely linked to the debates about VUCA and agility. Agile frameworks are quite successful and the call for an “agile organization” is meanwhile heard virtually everywhere. An important step on the way to agile organizations is on the one hand seen in “Agile Scaling”—the transfer of agile approaches from isolated teams to the organization as a whole. On the other hand, companies increasingly try to actively create their “business ecosystem”. Both agile ideas provide changes and risks for all stakeholders and are challenged by historically grown bureaucratic and hierarchical structures. This chapter argues that active management of contradictions is necessary and provides insights into core principles for agile management of contradictions.