to navigate the significant gendered barriers to women operating in executive institutions. A close comparison reveals the two leaders adopted a similar approach, styling themselves as 'heroic' and radical outsiders to govern within the masculine office of Prime Minister. In office, the two leaders adopted a comparable style, pursued a strong vision, and sought to closely control their inner courts. However, their performance and governing context made for very different outcomes. In their performance, Thatcher proved an adept communicator and operator, while May showed poor skills and communicative abilities. Moreover, while Thatcher navigated entrenched gender norms in an increasingly favourable context, May governed during the brittle politics of Brexit, over a far more deeply divided Cabinet and party.Although decades apart, as women, these two leaders were novelties and outsiders in executive office, a rare phenomenon in British politics (Fry, 2015). They governed through what were broadly the same set of executive institutions at the centre, led the same political party, and dealt with the same blend of personal and structural opportunities and constrains the self-same institutions created (Helms, 2012). Even the media coverage and gendered frames remained similar between 1979 and 2016 (Williams, 2020b).Both leaders faced the challenge of office by using their outsider status -styling themselves as heroic and radical outsiders. Furthermore, although May rejected any comparisons between herself and Thatcher, she consciously borrowed from her predecessor, famously doing an impression of her in her first Prime Minister's Questions (PMQs).Political leadership must blend 'skills in context', from individual skills such as vision and communication, to more relational attributes such as political support from powerful colleagues (see Heffernan, 2005;Seldon, 2021;Theakston, 2007). These skills can be seen as uniting leadership 'performance' with context and 'the interplay between personal, institutional and contextual factors' (Hargrove and Owens, 2003; Strangio et al, 2013, 1). Taking this as a starting point, we argue that successful leaders often blend three features: a particular (and, we argue, gendered) 'heroic' style; a strong vision; and clear control of their inner court. We compare thatcher and May's leadership against each of these elements in turn.Thatcher's longevity can be attributed, at least in part, to the fact that her leadership involved a 'heroic' role as a change agent, which was associated with a particular style, strong vision and -for much of her premiership -an ability to control her inner court. Meanwhile, we argue, May's heroic style came apart after the 'failed' snap election of 2017. May tied herself to more rigid aims with less care or caution than Thatcher and failed to communicate or narrate her approach, hence her attempts to control her Cabinet came rapidly unstuck.