The ability to flourish during a crisis requires a unique skill set focused on emotional, psychological, and social well-being. As COVID-19 swept the nation, academic administrators faced many difficult decisions surrounding emergency remote learning as well as the health and safety of students and faculty. While some leaders found themselves able to guide their teams and lead them to success despite the pandemic that surrounded them, others stumbled. This quantitative study surveyed traditional full-time faculty (FTF) (n = 29) and online full-time faculty (OFTF) (n = 51) at a Southwestern university to examine the relationship between faculty self-empowerment, faculty flourishing, and faculty chair servant leadership during the COVID-19 pandemic. An analysis of all faculty found a significant correlation between all variables. An examination of just the FTF respondents found a significant correlation between chair servant leadership and faculty flourishing as well as between faculty self-empowerment and flourishing, but it did not find a correlation between chair servant leadership and faculty self-empowerment. An analysis of the OFTF respondents found a significant correlation between all variables. These results indicate that higher levels of faculty chair servant leadership are linked with faculty self-empowerment and faculty flourishing. As such, promoting a servant leadership mindset in faculty chairs may be pivotal in promoting faculty effectiveness via increased self-efficacy (which may be of increased importance during times of educational turmoil such during the pandemic). Notably this relationship may be even more important in the online context, while outside sources may play a greater role in empowering faculty on campus.