A transformational leader, juxtaposed against a transactional leader, “engages with others in such a way that the leader and the follower raise one another to a higher level of motivation and morality” (Burns, 1978, p. 20). Through various mechanisms, s/he is able to infuse a vision that encourages followers to transcend individual performance norms and act in the collective interest (e.g. Bass and Avolio, 1990; Yammarino and Bass, 1990). Transformational leadership theory has recently been criticized for its limitations (e.g. Van Knippenberg and Sitkin, 2013). The challenge of organizational transformation in complex contexts requires far greater depth of theoretical examination, such as exploring possible combinations of individual and plural perspectives of leadership at the top of the organization (e.g. Denis et al., 2012); yet the literature continues to focus mainly on the individual leading the transformation, rather than on the plurality of individuals and their interactions (Kempster et al., 2014; White et al., 2016). Denis et al. (2012) advocate further exploration of when and where forms of plural leadership are necessary and effective. Following Johns’s (2006) suggestions and, in particular, taking account of the role of context to develop frameworks that illustrate specific contingencies affecting the implementation of different forms of leadership, this study focuses on the “omnibus” context and the process of leadership in transformation, illustrating the findings in terms of key actors, activities, and behaviors. The research question guiding this study is: RQ1. How does the context of an organizational transformation and its different phases affect the characteristics of individual and plural leadership, and the adoption of different transformation drivers? This study analyzes the results of an action research project developed with an Italian, family-owned fashion design company. The research focuses on organizational change from a leadership perspective and captures the dynamics of a family hiring a CEO that is not a member of the family. Family-owned organizations share many features in common with other firms, but the coupling of business and family relationships leads to specific organizational characteristics and dynamics, for example with regard to family succession and relationships between family and non-family members (Cater and Schwab, 2008). This study contributes to the literature by showing the role of context in accelerating the effective implementation of different forms of leadership and their relationship with individual perspectives over time, and how specific leadership manifestations, in terms of individual and plural manifestations of leadership and transformation drivers, may be observed during different phases of transformation.