Animal personality refers to individual differences in behavior that are consistent across time and across contexts. As it plays an ecological and evolutionary role for many animals by affecting fitness, it is likely to play a role in how both species and individuals fare in captivity. Assessment of animal personality by caretaker ratings has been validated using behavioral coding methods in a number of species and has thus become the most common method for assessing personality of captive animals. Whereas the reliability of rating methodology is arguable, the reality of working in a captive setting makes assessment of animal personality by caretaker ratings an easy and practical way to investigate questions related to personality. We used a case study in African lions to investigate the use of rating methodology to uncover personality traits. We then related dimensionality of those traits to fecal glucocorticoid metabolite values taken before, during, and after habitat renovation. The end goal was to devise a method by which individual welfare can be considered and improved by considering personality traits. Interobserver reliability scores revealed that only 11 out of 18 traits and four out of six lions were reliably rated. From those traits, we uncovered a sociability-neuroticism axis, whereby lions that were more social and less neurotic had lower glucocorticoid metabolite levels (GCM). In addition, we found that more vocal animals had higher GCM levels and more active animals had lower GCM levels, findings that suggest that vocalizing and activity level may be part of the way these individuals cope with stressors. These results suggest that a better understanding of a lion’s sociability and neuroticism may inform management decisions during stressful times. Further investigation into the two lions who did not pass reliability testing, revealed that they had the lowest number of extreme trait ratings which suggests that they may have been the most behaviorally plastic, a characteristic that was not expressly measured by the surveys. The inability of rating methodology to measure plasticity and the role of the human-animal relationship in contributing to low reliability scores are discussed. We suggest that the most widely used personality surveys may work well for animals who exhibit low levels of plasticity and whose behavior falls closer to the extremes of a continuum, but may be less helpful for more plastic animals whose personality traits fall in the mid-range.