In this paper we explore challenges facing leadership in a culture of “all consuming images” from a perspective which claims that images have a moral or normative dimension. The cumulative effect of contemporary image saturation is increased resistance to the normative power of an image. We also suggest that in a culturally diverse global economy, it is necessary to expand the moral aspects of good business leadership beyond providing a basis for productive, coherent group identity within a firm at the expense of seeing outsiders as “others.” We also explore what imagining leadership in business might be like in a world in which visual images shape our understandings of individual and group identity. While our focus is on leadership in business, we also use examples from the political arena. We also suggest that imagining business leadership in the ways we propose may be helpful to women, providing them with an image of business leadership more closely reflective of their experience of corporate culture, its limits, and possibilities.