This field-based case offers the experiences of a historic winery in Tuscany, Italy, to set the stage for how the leader's philosophy affects all aspects of the company, as well as how those practices create the culture of an all-female-staffed organization. The situation provides an opportunity to explore and connect the relationship among the leader's values, the actions she takes, and the impact of those values and actions on how the organization works. The case opens with the owner of Casato Prime Donne and Fattoria del Colle wineries, Donatella Cinelli Colombini, reflecting on strategic plans to increase production, build a warehouse, and grow the estates. In the long term, she would have to decide when a good time might be to step down from the business and pass it to her daughter. Had she built a self-managed team that could continue to grow the business and build future relationships between the wineries and tourism? Was her business sturdy enough to stand on its own when she left?