Today, women comprise nearly half the U.S. workforce and outnumber men in many previously male-dominated fields. This seismic cultural and demographic shift has dramatically impacted organizations. The most obvious impact is the presence of, and dependence on, increased numbers of women employees throughout organizations. Retention of talented working women is increasingly critical to business success. Yet, following maternity leave, the retention rate of working women drops significantly when compared to the average (non-maternity related) retention rate of working women. To compound the problem, when women return to work from voluntary time away (for any reason), they often return to lesser roles or in a diminished capacity with decreased chance of advancement. This significant reduction of female talent comes at great cost to organizations, women themselves, and society at large. This dissertation aims to address this problematic talent loss by offering RETAIN CoachingRTM, a new model and practice of executive coaching focused on supporting both women and their work organizations throughout an identified 3-Phase maternity leave transition process. These phases are: 1) Preparing for Leave; 2) Moving Through Leave; and 3) Returning from Leave. The proposed RETAIN Maternity Leave Transition Coaching Model and its custom tools, assessments, and resources, are academically-grounded in seven literature streams, including Nancy Schlossberg's Transition Theory; Adult Learning Theory; and Executive Coaching. To date, this dissertation offers the only known evidence-based theoretical framework for the emergent field of Executive Maternity Coaching. Proposed in this dissertation is: "a theoretical framework, a definition", and a "description" of maternity coaching; a "3-Phase transition process"; a "coaching practice schedule" for organizations and individuals; a "Maternity Leave Transition Questionnaire; a Maternity Leave Transition Sabotages Assessment"; and multiple tools and resources. RETAIN Coaching outlines a recursive coaching practice that guides coaches and clients through each of the R-E-T-A-I-N components: Relate; Explore; Tailor; Assess; Instruct; and Next Steps (action planning). It is hoped that this model will help women, their managers, and their organizations, navigate the complex maternity leave transition time period in more effective, engaged, supported, and sustainable ways, that ultimately lead to the increased retention of valuable employees. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]