Now, more than ever, the baby-boomer administrators are retiring in massive waves. Some researchers have predicted as high as 75% turnover by 2011 for education alone. For many years, not much attention has been placed upon succession planning or developing new leaders in some colleges; others have tended to create stockpiles of leadership candidates with not enough internal leadership positions to go around. In turn, in many schools this has left the talent pool of qualified individuals to be very small, and it creates a problem, not only for educational administrators but also, especially, for those in the entrepreneurial departments of community colleges. There has been much research about "getting the right person on the bus" and "moving from good to great," yet no one, to the knowledge of the researchers, has extended industrial-organizational psychology research on "person-fit" into community college administration research. The purpose of this study was to examine the theoretical constructs of the educational hiring process. In turn, the application of the Lessig "Pathetic Dot" model is used to create a framework to examine hiring practices and possibly show some deficiencies. This is important, now more than ever, with community college administrations having to turn to external independent sources for validation of their practices and procedures. Finally, a brief discussion of how to strengthen the hiring process, in a time of heavy turnover and attrition, concludes the discussion. The authors also present practical applications, suggestions for future research, and implications for practitioners. (Contains 2 figures.)