Since 1991, 10 women have served as chief executives at the provincial level in Canada. Of these, six were directly selected to the post by their parties. What accounts for the selection of these women directly to the premier’s office? This paper proposes four hypotheses that may explain why political parties would choose women as leader and/or chief executive: crisis through electoral defeat, crisis through scandal, party decline, and policy failure. Preliminary evidence is found for some women’s selection in times of crisis and decline, though this preliminary evidence is not very strong. Though women were selected party leader and premier after policy failure, these instances are not congruent with gender stereotypes about policy competence. Other women were selected premier when their parties were strong and stable. More research is required to fully understand these patterns before we can draw generalizations about when and why some women are selected directly to the premier’s office.