The need for skilled senior leaders within community colleges has long been acknowledged. This study identified and explored preparation factors which may contribute to the development of outstanding community college leadership skills;Surveys designed to collect both demographic information and information on the respondent's leadership preparation were sent to all presidents of public, two year institutions located in the Upper Midwest. A return rate of 85% (125/147) was achieved. A peer rating method was used to divide the respondents into two groups; outstanding/leading and normative;Demographic data from the two groups were compared. The peer selected outstanding/leading group was 100% Caucasian, predominately male (94%) and without exception married;Nine preparation factors were identified during the literature review that may contribute to the development of leaderships skills appropriate for a community college setting. These factors are: (a) an earned terminal degree, (b) a major within the terminal degree focused on the study of Higher Education/community college leadership, (c) a research and publications agenda, (d) specific preparation as a change agent, (e) identification as a community college insider, (f) participation as a protege in a mentor-protege relationship, (g) involvement with a peer network, (h) leadership development activities outside of their graduate program, and (i) knowledge of technology;The outstanding/leading presidents displayed a higher rate of having earned a terminal degree (94% versus 80%), a higher rate of having majored in Higher Education/emphasis on community college leadership (53% versus 32%), a higher rate of both publishing and presenting scholarly work (published within the last 5 years, 59% versus 25%; presented within the last 5 years, 53% versus 35%), and more involvement with both peer networks and mentors. Additionally, outstanding/leading presidents displayed a higher rate of non-traditional paths to their presidencies;A statistical test for comparing two binomial proportions identified statistically significant differences between the two groups on 4 of the 9 identified factors (terminal degree attainment, majors which focused on community college leadership, production of scholarly work, and involvement with a peer network).