The challenges with which college and university boards must grapple promise to become only more complex in the coming years, placing ever-greater demands on the leaders of those boards. This article presents a conversation between Association of Governing Boards of Universities and Colleges (AGB) President Richard D. Legon and two AGB leaders who were formerly board chairs at very different higher-education institutions--James M. Weaver and Cynthia A. Baldwin--for their insights on a variety of issues related to the governance of higher education.