A body of scholarship on the history of the lives of Catholic teaching sisters has thrown up various challenges to educational historians. One challenge can be posed by asking how teaching sisters were able to go on to take up leadership positions. This is prompted by the observation that a particular body of literature for the period 1940-1965 indicating that they underwent a strict "formation" regimen intended to prepare them for total obedience to their superiors, inculcate in them a non-questioning attitude and deprive them of opportunities to take initiative, how then were they able to go on to take up leadership positions? The paper outlines the results of an oral history project which addressed this apparent paradox in the case of a group of women who worked as sister principals in Ireland. The results suggest they had a significant amount of freedom and room for questioning and initiative, and that this stood them in good stead when they went on to become sister principals.