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We propose a theory of interests, incentives, and capacity to predict when cabinet ministers could be expected to expand representation of historically marginalized groups. This theory merges work from feminist institutionalism and formal models of cabinet drift to generate new implications about when, why, and for whom cabinet members represent the interests of politically marginalized groups. This theory recognizes the diversity of representational interests within women and men, incentives or constraints imposed by the desire to build a political career, and differing capacity that can shape which groups a minister acts to represent. We test this theory with analysis of executive decrees issued in the cabinets of two presidents in Costa Rica that come from different parties, one woman and one man: Laura Chinchilla (PLN, 2010-14) and Luis Guillermo Solís (PAC, 2014-18). Costa Rica offers an ideal pilot case due to the country’s extensive history of incorporating women into cabinets. A challenge to studying representation by cabinet ministers is that policy deliberations occur “behind closed doors”. To circumvent this problem, we focus on executive decrees, one of the observable actions of cabinet ministers that, due to their bureaucratic nature, are less publicly visible than new legislative initiatives. We compile the relevant text using supervised machine learning algorithms, and this text-as-data allows us to compare initiatives drafted under female and male ministers during these two presidential administrations. Our paper analyzes more than 600 executive decrees from the ministries of Agriculture, Education, and Justice. These portfolios afford variation in the minister’s sex across or within administrations and allow us to study representation in a stereotyped masculine, feminine, and neutral policy area ministry. Preliminary findings indicate that the study of executive decrees is fruitful, as it has uncovered chapters within bureaucratic decrees that focus on women’s rights (e.g., protection against sexual harassment) and that specify the needs of women, young people, indigenous people, poor people, and people with disabilities in the agency’s programs.