Metaphors are devices that help us connect new information and experiences to that which is already known to us (Lakoff and Johnson 1980). Research suggests that metaphors are an important aspect of processing new concepts (Boxenbaum and Rouleau 2011) and that metaphors are used more widely in education than one might initially realise (Guilherme and Souza de Freitas 2018). We connect new experiences to those that help us make sense of the unknown and we often absorb metaphors for knowledge, experience, and practices unconsciously (Lakoff and Johnson 1980). Metaphors abound in education, and in educational leadership. Metaphors can be seen as neutral descriptors but, in reality, are anything but neutral. Paetcher (2004, 460) describes the ideological force behind metaphors and notes that metaphors steer us into ways of thinking about, and going about, the process of education. While metaphors condense complex ideas into familiar ones (Paranosic and Riveros 2017) and can thereby help to make meaning, the nature of metaphors needs to be critically interrogated to better understand the underlying assumptions and beliefs behind them. For example, dominant leadership metaphors are drawn from military and sporting contexts (Edmonstone 2016; Ashcraft and Muhr 2018) and such metaphors invoke 'unflinching strength, toughness, and even brutality' (Ashcraft and Muhr 2018, 208). Dominant metaphors draw heavily on the notion of the great hero leader (Woods and Roberts 2018) and on masculinist constructions of leadership; an ongoing issue in educational leadership (Wilkinson 2008) that is addressed by some of the papers within this Special Issue. Alvesson and Spicer (2010) suggest that critical scrutiny of metaphors can push us to examine the assumptions behind how we conceptualise leadership. We want to ask: Does this metaphor of leadership present the vision of leadership that we want to see enacted in educational settings? Does this metaphor move conceptions of educational leadership forward or unquestioningly perpetuate tired or harmful leadership paradigms? Moving beyond dominant and traditional metaphors of leadership can provide more interesting, inclusive, and productive ways for us to understand leadership. Fairhurst (2010) suggests that leaders who can draw upon a wider variety of metaphors to enact their work will be better able to meet the varied demands of their jobs. Similarly, Guilherme and Souza de Freitas (2018) indicate that metaphors act as an enabler to bring forth a diversity of perspectives and possibilities. Hoyle and Wallace (2007) reason that the most productive starting point for metaphors is to find and develop the metaphors that leaders actually live by. The papers in this Special Issue draw upon metaphors articulated by research participants, as well as metaphors that appealed to the contributors when considering their work within the field of educational leadership.