As a faculty dean, I was constantly surprised over the years by the number of female academics who expressed reluctance to do my job. Why were they so reluctant? Why did they cite intense argument and personal criticism as significant deterrents? Focusing specifically on academic argument, and the crucial role of autonomy in academe, this paper will identify and explore two discursive orientations often found in university culture today that have the potential to limit autonomy. It is argued that their presence creates a peculiarly challenging environment for female academic leaders. Drawing on relevant philosophical literature and my own personal experience as a member of senior academic administration, the paper will examine the nature of the challenges entailed and the insights it may provide into females' reluctance to become academic leaders. Challenges notwithstanding, it is hoped that the personal perspective brought to bear on the discussion will encourage female academics to see beyond potential barriers and to pursue leadership as a realistic, worthy option in their professional lives.