A typical company’s corporate planning department in Japan, is under the direct control of management, and the majority of its work is to deploy management’s instructions within the company rather than to think and act on its own. As a result, members of the corporate planning department, which is supposed to function as the core of the company, have a strong sense of being told to do what they are told, resulting in a sense of stagnation. As a result, the motivation of the members of the Corporate Planning Department declines, and there are concerns about the health hazards associated with this. To solve these problems, we introduced on-on-one meeting, education and training, and behavior change initiatives to increase the motivation of the members of the Corporate Planning Department. We measured members’ motivation by conducting a pulse survey after each initiative, calculated the effectiveness of each initiative, and used a Monte Carlo simulation to determine the most effective way to order the initiatives. According to the results of the pulse survey, when corporate planning team members are forced by their supervisors to follow a one-on-one meeting policy, their performance generally worsens; however, they may be easily influenced by their management philosophy, and other indicators may increase. And from the results of the simulation, a one-on-one meeting does not appear to have an effect if started early in the organization’s formation. By contrast, conducting a one-on-one meeting after an ice breaker, such as behavior change or education, in which members collaborate with each other, is considered effective. However, it was found that the effect gradually became the same as the number of simulations increased.