Leader derailment of middle managers in higher education is most often attributable to self-defeating behaviors (SDBs) and problems with interpersonal relationships (PIRs). This study attempted to determine whether training provided for middle managers in Academe sufficiently addresses these issues. Our findings suggest that while little more than half the responding institutions provided some sort of training to first-time administrators; it was focused mostly on administrative issues. Less than half of the surveyed institutions offered any kind of training relating to PIRs or SDBs. We end the paper with recommendations and suggestions for improvements in training programs aimed at decreasing the incidence of leader derailment in Academe.