Indian Women today carry the legacy of a civilisation thousands of years old; this legacy is paradoxical, in that it can be both a burden and a source of inspiration. The challenge is to distill the best from the past, transform ancient wisdom into modern day paradigms and not be shackled by the bondage of age old dogmas and beliefs! Indian Women and Indian society as a whole has moved from well-entrenched gender-centric roles, (where Man was considered the leader and provider and Woman the idealised deity, but submissive and subservient in day to day matters), to today's revolutionary thinking that is emerging, partly due to education and western influences, where roles are not stereotyped by gender and allow men to recognise their feminity and women their masculanity. This transformation is far from complete; however important beginnings have been made particularly in large metropolitan cities in tomorrow's industries where enabling technologies have brought dramatic changes in terms of creating virtual work spaces. The objective of the four day workshop conducted at the Indian Institute of Management, Ahmedabad, for women managers/leaders in October 1999, was to explore the influence of the transformation of organisations on women's roles in the corporate world; to explore their leadership roles and also their life-spaces; to discover wholesome ways to actualise dreams and chart new career paths. The programme was divided into two modules, Conceptual and Experiential. The conceptual module explored the impact of transformation in organizations and on individual employees, particularly women. In the experiential module the exploration was around life-spaces and systems where processes of socialisation in both family and work setting were understood. How did women who are impacted by these diverse interfaces give shape to their roles? The paper discusses the experiences of the participants at home and at work place. The shift in mindsets of people and society have contributed to a lot of positivity in terms of women's acceptance as capable, hardworking and committed professionals and individuals. On the other hand they did feel that there was a constant pressure to perform and prove themselves at work place and simultaneously, a constant feeling of guilt and anger in coping up with expectations of children and in-laws respectively at the home-front. They were indeed successful in striking a balance between home and work and in doing so not many had managed to take leadership positions which was still very much considered a man's domain. An important and interesting issue which the paper further discusses is the exploration of women's life spaces, their identity and the roles they take, especially in terms of leadership. The life-space of women vis-à-vis home/family and also vis-à-vis work place is analysed and discussed by the participants. At the home from the dynamics of in-laws, especially the interface of the women with their mother-in-law, their experience of motherhood and the dynamics of relationships with the husband- all contribute to dilemmas of marriage. The women shared some of their personal experiences related to their entry into the workspace and their interfaces with the superiors, colleagues and subordinates of both genders. The dilemmas faced by women in terms of assuming leadership roles, climbing corporate ladder and contributing to decision making processes in the organisation are, anchored in the socio-cultural context as well as in the maps and definitions they carry from the past. A future scenario was painted by the participants. For the first time in recent history women have begun to assume leadership roles in the corporate world and are hopeful of blazing new trails for future generations, creating new role-models and cracking, if not, shattering the glass-ceiling. Women can look forward to the future with optimism. Women are experienced in managing one of the most complex organization imaginable – the household, and therefore can apply their skills and experiences in terms of hard-work and sensitivity in managing relationships, at the work place. The authors have discussed how women could be successful leaders if they achieved a congruity between their inner-instincts and their career goals! The Indian Woman today is at a threshold where she is confronting not only herself and her own inner feelings, historical conditioning and fears, but also managing interfaces in the outside world both at home and work place. As recent role-models demonstrate, women tentatively are crossing this threshold, challenging themselves and blazing a new path for future generations. The new Millennium may well usher in an era, where not only women but the entire human race can more easily achieve self-actualisation and total fulfillment both professionally and personally. The leaders of tomorrow would be such that they would not be identified by their gender, but by their capability and meritocracy.