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Enterprise systems are complex and expensive and create dramatic organizational change. Implementing an enterprise system can be the "corporate equivalent of a root canal," a meaningful analogy given that an ES with its single database replaces myriad special-purpose legacy systems that once operated in isolation. An ES, or enterprise resource planning system, has the Herculean task of seamlessly supporting and integrating a full range of business processes, uniting functional islands and making their data visible across the organization in real time. The authors offer guidelines based on five years of observing ES implementations that can help managers circumvent obstacles and control the tensions during and after the project.