As technical management skills in expressway projects are changing depending on the site conditions and social conditions, we examined the definitions and methods for developing skills based on the Successive Approximation Model, in which evaluations are repeated at each phase, including preparation, design, and development stages. First, the essence and points required to strengthen skills were determined using interviews and questionnaires. Next, we developed a curriculum map by implementing actual tasks with strengthening of these points. The curriculum map was then improved by a case study. Finally, we developed evaluation criteria and instructional tools in a trial experiment. The evaluation yielded novel findings at each stage. For example, the core competence of technical management was similar to symbolic interactions between stakeholders, and the method for skill development allowed leaders to gain a “multiplier” leadership style that encourages the growth and creativity of employees. In addition, educational benefits were obtained by participants' independence, which was fostered by the high degree of freedom in the trial experiment.
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