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Although theoretical and applied work has emphasized the critical role of coachee personality in the coaching process, little empirical research has identified specific personality traits as moderating variables. Drawing from social-psychological theories, we examined coachees’ ability to modify self-presentation, a major facet of the self-monitoring construct, as a moderator of the relationships between executive coaching and coachees’ satisfaction with the coaching relationship, career-related self-reflection, and self-esteem. Using a sample of managerial coachees who were either unemployed or at risk of becoming unemployed and who participated in a series of executive-coaching sessions, we found support for most of our hypotheses. Overall coaching as well as specific coaching factors were significantly and positively associated with relationship satisfaction and self-reflection. Overall coaching and transformative-learning dimensions of coaching (goal development and past reappraisal) related more strongly and positively to self-reflection among coachees high in self-presentation ability, whereas overall coaching and psychosocial dimensions of coaching (confidence enhancement and relationship building) related more strongly and positively to relationship satisfaction among coachees low in self-presentation ability. Therefore, our theoretical considerations and empirical results suggest that coachees differing in self-presentation ability respond differently to coaching in general and to specific coach behaviors in particular.