Leaders in higher education are well aware the critical issues they face—relevance, value, and sustainability. They are working to navigate an educational landscape that is complex and changing, and seeking to craft responses to these issues. A major concern, however, is the extent to which leaders are both equipped for, and willing to address, some of the major critical challenges facing the academy. Recent survey data suggests no shortage of activity at colleges and universities. The question is whether “out of the box” solutions are even possible given the culture of higher education.