This chapter attempts to gather and synthesize the thinking on the convergence of gender and leadership in rural areas across the developed world, with how leadership is generally conceptualized, defined and enacted. Despite the European Union's legislative reforms regarding gender-neutral leadership selection criteria for organizations, the hoped-for increase in women in organizational leadership in the EU has not taken place. The European Union, women are less likely to attain leadership positions in for-profit organizations than in non-profit organizations. The gender shapes ideas of leadership are powerful, and rural women have operated within a social system that prioritizes tasks associated with males over tasks associated with females. For people of all genders, self-identification as leader is complicated by prevailing theories of leadership, which conflict in their assertions regarding whether masculine, feminine or androgynous leadership is most effective. Stereotypes around masculine and feminine behaviors have varying influence on perceptions of leadership effectiveness, dependent upon social context and the success of the organization.