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The purpose of this chapter is to examine how leaders furthered the development of a social enterprise in response to paradoxes. Data on leadership practices were collected through interviews and observations in an Italian Healthcare network over the organization’s first two years. The data indicate that leaders addressed paradoxes in developing several critical resources by using both top-down influence and bottom-up participation. Leaders used top-down practices to further organizational development along a known path when they could leverage technical expertise or a vision to address a source of tension. Bottom-up practices, on the other hand, permitted the discovery of new paths that had not been previously identified. Leaders leveraged such responses where tensions appeared intractable. Implications for managers and organizational development and change practitioners are discussed.

This chapter focuses on an innovative effort in the Italian context in which a complex web of partnerships was created as the foundation of an alternative model of health care. More specifically, the start-up of a health-care organization – Welfare Italia Servizi (WIS) – is analyzed and discussed with respect to its sustainability.

The process of organizing a sustainable health care is analyzed through the theoretical lenses of multi-stakeholders management and partnership perspectives.

The possibility of developing dense knowledge about the WIS’s case has stemmed from our collaboration with the organization board with regard to a research process intended to monitor the organizational start-up and its sustainability challenges.

The case provides new insights into the dynamic nature of building multi-stakeholder partnership in a complex environment; the developmental life-cycle challenge of multi-stakeholder partnership, and the meaning of sustainability. The case suggests a tapestry of issues such as how sustainability may be “paradoxical,” dynamic, led by different and sometimes conflicting logics, and changeable over time like a growing tree in an intricate forest.

The case can stimulate learning and discussions both within the community of practitioners and the community of academics with respect to which promising conditions could help address the challenge of starting-up a sustainable organization in the health-care field.