Women politicians face a paradox when acting in parliament: on the one hand, substantively representing women pushes women who are members of parliament (MPs) to have a more gendered style and to sometimes focus their activity on so-called “women’s issues”, such as education and healthcare. On the other hand, many voters have a gendered perception of politics, and have harsher evaluations of women politicians. We investigate how these contradictory incentives have influenced women’s parliamentary trajectories in nineteen democracies around the world between 1987 and 2020. We collect more than 11 million parliamentary speeches from those countries, and apply machine learning models to predict, whether each speech was given by a woman or a man. The predictive accuracy is taken to represent the degree of genderedness of the speech and respective legislator: when the classifier has a high certainty that a speech was given by a woman, it is an indication that the speech contains more feminine gendered language. Subsequently, we investigate the relationship between discourse genderedness and women’s progression in parliament over time, more specifically the relationship with tenure, and how they rise through party ranks. Preliminary findings suggest that women MPs have a less distinctively feminine voice the longer they stay in parliament, and that joining the cabinet erases much of the difference in speaking style between men and women MPs. This research helps us understand the individual incentives that shape how women represent women in parliament and the institutional structures that influence this relationship.