In this paper, we explore the idea of managerial struggle and pedagogy as modes of manoeuvring in our examination of prolonged organizational transition and change inertia in the wake of privatisation of a Scandinavian telecommunications company (Telco). There is a lack of studies that, from the perspective of (middle) managers, attempt to understand seemingly inefficient leadership and how managers manoeuvre the complexities of change inertia, including how managers seek to gain control when they face difficult and complex and paradoxical conditions of leadership (Denis et al., 2010; Lüscher and Lewis, 2008; Filstad et al., 2020; Gatenby et al., 2015; McCabe, 2014; Alvesson and Sveningsson, 2003). We suggest a Bourdieusian conceptualisation of manoeuvring using Bourdieu’s (1990) concepts of field, habitus, symbolic violence and pedagogy, where we see pedagogy as an overlooked part of managers manoeuvring practices that emphasises the use of power and relations of power in managerial practice (Kamoche and Pinnington, 2012; Tomlinson et al., 2013). We develop our arguments through empirical studies of seemingly inefficient leadership by a team of frontline managers in the operations department of Telco. Comprising 185 hours of participant observation studies and 25 interviews with the regional director, frontline managers, and technicians, our study examines how the frontline managers struggle to manage during prolonged attempts at organisational transition from state-owned monopoly to shareholder-owned corporation. The capitalist visions and ideas of the American owners contrast sharply with the socalled Nordic Model of work and welfare according to which the company had been run and whose central features are a high rate of unionization among employees, a national hierarchical system of collective bargaining, and the powerful presence of trade unions at workplace and national policy making levels (Ervasti et al., 2008; Kettunen, 2012). The shift to a more active and intervening role has placed the frontline managers in the eye of a storm. We show how the frontline managers perceive themselves as tasked with supplying the technicians with the understandings, beliefs and dispositions for action that will enable them to meet demands associated with corporate neoliberal capitalism (Visser, 2020; Arturo, 1994) and how they must respond to outspoken yet subtle contradictions in their manoeuvring space (Filstad et al., 2020) or their possibilities for ‘playing the game’(Bourdieu, 1990). The idea of managerial pedagogy as practices of inculcation of beliefs and dispositions, in particular, and its connection to relations of power and symbolic violence (Lakomski, 1984; Tomlinson et al., 2013; Kerr and Robinson, 2009; Kamoche and Pinnington, 2012), allows us to extend the use of Bourdieu in studies of management and organization when we provide new insights into prolonged organizational change inertia and managerial struggle. We argue that pedagogy, as part of middle managerial manoeuvring, enables a vision of the multitude of power relations at play in organizational change, and beyond, including the fastening of these power relations in structural and historical conditions of the field in which the organization is embedded.