Researchers suggest contextual and personal factors may interact to predict career adaptability and that antecedents of career adaptability have received less research attention. Consequently, we examined the relationship between developmental leadership, career optimism, and career adaptability, and the potential moderating role of career optimism. Data were collected from workers pursuing an MBA program in leadership and other business courses in a Ghanaian University. Results showed that developmental leadership and career optimism relates positively to career adaptability. Finally, we observed developmental leadership relates positively to career adaptability for employees low on optimism but was unrelated to career adaptability for employees high on optimism. Together, the results suggest that although both developmental leadership and career optimism are beneficial for career adaptability, developmental leadership is particularly important, for less optimistic employees. We have discussed implications and limitations of our findings.