In this chapter we look at how some unique aspects of gender in family-owned businesses (Casperz and Thomas, 2015) set them apart from other types of organizations. We give a brief overview of the mainstream theories of leadership and gender. Some of these, including the ‘great man’ theory, lie at the heart of leadership and management theory and represent different schools of thought (Bolden et al., 2003). The great man theory, which conjures up an image of a western male military hero, has strongly influenced leadership thinking (Collinson, 2011). This influence was demonstrated by research at Colombia Business School in New York, the Howard/Heidi research study. Students were asked to evaluate a non-existing person, ‘Howard’s’ résumé’. They considered it impressive and pronounced Howard a leader they would like to work for. A peer group was given the same résumé with a slight change in name – the non-existent Howard became Heidi. Students evaluated her as equally effective but rather selfish and someone they would be less eager to work for (Muir, 2012). The stereotypes demonstrated in this study are that we align our perception of certain characteristics, competences and associations with male and female leaders (Collinson, 2011), regardless of their effectiveness.