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The number of women holding elite-level positions in politics and business have significantly increased in recent years, but the lack of parity between the genders is still apparent. This article addresses the stereotypical thinking and the double-bind dilemma women face in obtaining promotions to top positions. It posits internal obstacles that stem from early socialization and may be worked through therapeutically. It proposes that individual psychoanalytic psychotherapy, in the context of object relations and attachment theories, combined with group therapy can facilitate intrapsychic growth towards leadership. Participation in a time-limited group for women may further their insight into the underlying barriers to top positions and facilitate the learning of how to move from fitting in to having a voice and becoming more independent and assertive. Women cracking the glass ceiling may contribute to external societal changes as the relational style of women will continue to gain momentum and redefine leadership in the workplace. Clinical examples will illustrate the therapeutic interventions.