Personality approaches to politics are often criticized for not examining the effect that institutional role constraints have on individual beliefs and preferences. When leaders appear to change their stance when they change roles, it is assumed that roles have a determining influence. Modern personality theory and contemporary sociological role theory, however, view the effects of roles as interacting with agents’ personalities. In this article, we investigate this question by comparing personality profiles of three Turkish leaders (Özal, Demirel, and Gül) during their tenure as prime minister and during their subsequent time as president. For Gül, we perform an additional comparison during his time as foreign minister. The personality profiles are in the form of quantitative scores generated from machine‐coded content analysis of leaders’ words using the Leadership Trait Analysis method. We hypothesize that different leaders will be more susceptible to changing role contexts, depending on core personality traits, and that different traits are more likely to change with new roles. Overall, our results suggest that leaders’ traits are fairly resistant to changes across roles and that task orientation is the most likely trait to change as leaders adapt to different role demands and expectations. This study makes a contribution to our understanding of the interaction between personality and political contexts by offering specific theoretically derived hypotheses and by empirically and statistically examining a preliminary set of expectations that could be applied more broadly to other leaders.