Workplace flexibility has attracted much hope as a way to improve the effectiveness of the organization as well as to help the work-family balance. In the field, however, it is difficult to spread. We conducted a study focusing on work of smart work center as the space flexibility program. We interviewed 20 workers who had experience using the teleworking in 4 organizations and analyzed the process of using the smart work center and the conditions of successful settlement through the procedural framework of grounded theory. This analysis led to a consistent pattern, from the casual conditions in which the program is introduced until the work practices change leading to personal, organizational positive results. As a result, we found that a systematic organizational change effort in the early stage of the utilization of the smart work center program lead to positive results and to expand utilization. In other words, to establish successful workplace flexibility, 1) smart work center program users and the surrounding organizations have to proactively change the boundary management strategy between work and home, 2) strive to maintain the relationship within the workplace, and 3) redesign the way of work with work unit. If the only adaptation effort to the program is at the individual level, the positive effect of the program is experienced only at the individual level and does not spread to the organization level. If the trial and error that occurred early in the utilization of the program are not systematically managed, it was confirmed that the level of the workplace flexibility could be worse than before. The systematic adaptation effort at the organizational level causes the positive effects of the workplace flexibility to be experienced, which results in a virtuous cycle structure that leads to a gradual change in organizational culture, organizational effectiveness, and further utilization of the program.