The last thirty years have seen significantly more women reaching senior professional positions and a corresponding increase in women returning to work after having children. However, studies reveal that employers often lose highly qualified women, who choose not to return. The economic costs and implications of this ‘brain drain’ are significant. This research involved interviewing ten women, three coaches, and one purchaser of coaching, in order to study at the specific issues facing women returning to work and whether coaching can affect retention. The emerging issues that affected retention are: career development paths, the need for flexible working, corporate culture, and the need for work/life balance. Seven stages of transitional perspectives of work are proposed which reflect altering attitudes to work and which offer a relevant starting point for coaching support and interventions. As an external framework, coaching can support women effectively, in the short and long term, to meet the challenge of realigning work expectations and priorities.