We examine how leader optimism and leader-member exchange (LMX) influence follower career optimism, self-efficacy, and perceived leader effectiveness across military and civilian contexts. Drawing on relational leader theory, the Pygmalion effect, and positive organizational behavior, we contribute to the understanding of how leadership behaviors may differentially affect followers based on the environment in which they operate. An experimental vignette methodology (EVM) was used, manipulating leader optimism and LMX across eight conditions. The sample (n = 343) included both military personnel and civilian employees from 42 U.S. states to explore contextual differences. Results from independent samples t-tests revealed significant differences between groups in key follower outcomes. Perceived leader effectiveness (PLE) was significantly higher for followers with optimistic leaders and high-quality LMX relationships across both contexts. However, the most striking contextual difference emerged in self-efficacy (SE), as civilian employees’ self-efficacy was negatively impacted by pessimistic leadership, while military personnel showed resilience to such pessimism. These findings suggest that military personnel, potentially due to their training in high-stress environments, may maintain higher self-efficacy in the face of negative leadership behaviors, unlike their civilian counterparts. This study highlights the importance of considering follower experience and background in leadership research, offering practical implications for tailoring leadership approaches in civilian and military organizations. Theoretical contributions include insights into the role of leader-follower dynamics and the interaction effect of follower experience and background on follower outcomes. Keywords: Leadership, optimism, LMX, self-efficacy, leader effectiveness, military, civilian, experimental vignette methodology