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The deployment of social media inside and across enterprises, i.e. 'enterprise 2.0', has garnered significant attention, not least due to considerable levels of market push and hype from technology vendors, benchmarking institutions and consultancy firms. However, for some organizations, encouraging open and uninhibited knowledge exchanges may actually clash with past habits of relying on designed and structured strategies to manage communication. This paper has two objectives: first, to propose a set of management challenges inherent to the deployment of enterprise 2.0, and second, to incorporate these challenges into a collaborative management workshop process and group decision support system (GDSS) that encourages organizations' leadership teams to consider those challenges mindfully and collaboratively - before jumping on the enterprise 2.0 'bandwagon'. The paper follows Hevner's cycles of design science. For the system's design, we draw on theories of episodic change of general systems theorist, Luhmann and work by Churchman on inquiry systems.