The definition of leadership changes over time, and the language used to describe leaders is key to understanding what is acceptable and desired in those who lead community colleges at the highest level: the presidency. Language is inherently political, so the discourse around the qualifications of and expectations for presidents has the power to shape who sees themselves in those roles and whose image is forefront in the minds of search committees and campus members. We engaged in feminist critical discourse analysis of job postings for community college presidents at two points in a 20-year span, 1996 and 2016, to better understand how leadership is defined at the presidential level in the community college environment and, more importantly, who fits the profile of a leader. We found that although a counterdiscourse exists, the predominant discourse remains couched in outdated ideals of hero leadership that favors men.