This is a great time for individuals aspiring to the community college presidency. According to the 2012 American College President Study by the American Council on Education, in 2006, 47 percent of community college presidents were 51 to 60 years old and only 37 percent were between the ages of 61 and 70. More than five years later, 51 percent are 61 to 70 years old. This means more than half of all current community college presidents are either ready or will be ready within a couple of years to exit the presidency and retire or transition into another career. How best should the rising tide of presidential candidates prepare for their first experience negotiating a presidential contract? This article is based on numerous years of experience working with aspiring presidents and representing the interests of college governing boards in the negotiation process. The intention is to offer some general guidelines on how to prepare for the negotiation process.