This chapter investigates several aspects related to women leaders’ career development in unstable economic environments. The study is conducted in Greece which has faced very hard austerity measures due to the recent economic crisis. The sample consisted of 303 women who currently hold a managerial position in the private sector. Leadership style was measured using two different psychometric tools: the MLQ and the LMX-7. Career self-efficacy was measured using the Perceived Self-Efficacy in Career Scale and job insecurity was assessed by the Job Insecurity Scale. The study confirms the anticipated correlations between the various psychological constructs. Job insecurity is negatively correlated with all factors of both career self-efficacy and transformational leadership. Nevertheless, correlation coefficients are rather low. Career self-efficacy is positively correlated to transformational leadership. Intellectual stimulation was highly correlated with all self-efficacy components and especially with creativity. Results are discussed in terms of their practical implications.