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Technical advancement is predicted to impact the workforce and will require the reskilling of many. This study sought to understand the preparations large enterprises are taking to prepare their workforce and their workplace for the impact of advanced technologies. Specifically, this paper explored the knowledge, motivation, and organizational influences that impact the Chief Learning Officer’s (CLOs) ability to prepare their workforce for the future. Clark and Estes’ (2008) gap analysis model influence the conceptual and methodological framework for the study along with the Burke-Litwin (1992) model for organizational change. Interviews were conducted with seven CLOs at large enterprises. The research explored the CLOs’ knowledge and motivation related to creating a leadership and development strategy to develop their workforce, considering their organizations’ adoption of advanced technologies. The data suggested CLOs are knowledgeable and motivated about preparing their workforce for the future of work. The research also explored how organizational culture and context supported or hindered CLO knowledge and motivation. The data suggested that indeed organizational cultural models and organizational cultural settings impact the CLOs’ ability to reach their goals. Recommendations for developing a transformational adult learning program for CLOs was proposed. The program design, metrics and critical behaviors needed to evaluate the effectiveness of the proposed program was influenced by Kirkpatrick model by also took an anagogical approach. The practices identified supported the continued development of knowledge, motivation and organizational cultures to help prepare large enterprises’ workforce and workplace for the impact of advanced technologies.