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This thesis examines the nature of transition expertise which enables individuals to make repeated successful transitions over the course of their career. It addressed four areas that contribute to transition expertise: 1) cognitive flexibility that enables the generalisation of expert knowledge and processes; 2) inferential and inductive cognitive mechanisms that enable expertise to be generalised; 3) personal intelligences that are used to support transitions; and 4) practical intelligence as it supports performance contextually during transitions. The study used retrospective interviews to gather data from elite performers in three fields who had made successful career transitions: sports people who become national coaches or heads of national bodies; successful musicians who become heads of faculty or principals of a conservatoire; successful business people who become senior vice presidents or CEOs. Participants were able to generalise expert knowledge and processes beyond their primary domains, contrary to widely held views about the domain specificity of expertise. Cognitive flexibility enabled this generalisation and was developed through broad based training, early exposure to multiple domains and the early use of generative cognitive processes during the development of primary domain expertise. Inductive, inferential and analogical cognitive mechanisms were the main tools through which expertise was generalised during transitions. Personal intelligence contributed to transition expertise. Intrapersonal intelligence enabled individuals to understand how their abilities, values and motivations shaped their career progression. Interpersonal intelligence enabled individuals to respond effectively to the requirements of their peers, direct reports, stakeholders and organisational context. Contrary to expectations, self regulatory processes did not play a central role in the management of transitions. Practical intelligence enabled transition expertise. It involved more than applying subject-area and tacit knowledge. It encompassed the abilities to: identify and resolve problems; manipulate environmental objects in the form of administrative tasks, schedules and plans; utilise resources in terms of people and materials; and shape their environment, corporate structures and culture. Transition expertise develops and evolves over the course of a career as it uses convergent and divergent cognitive processes, inductive mechanisms, personal awareness and cognitive pragmatics to address issues of increasing scope and implication. While motivational factors, self belief and personality resiliency are important contributors to transition expertise they did not form part of this study.