Abstract
While companies are introducing or considering digital transformation (hereinafter referred to as DX) as a management strategy to strengthen their competitiveness, there are scattered cases where companies cite issues related to the field, such as ”lack of understanding in the field” or ”a gap between management and the field” from the initial stage of activities. This suggests that when the project progresses to the operational phase, it may not be utilised or function in the field and may be a temporary fix. The aim of DX is to optimise the business structure itself by utilising digital technology in order to achieve sustainable development and improve competitiveness in an uncertain business environment. And it is not only through optimisation, but also through the mindset of the frontline that proactively generates ideas and the so-called frontline capabilities that enable the frontline to flexibly create new value, that the introduced mechanisms can continually evolve. Based on our case study, this study examines the critical thinking of the driving leader who leads DX activities, using double-loop learning (C. Argysis /D.schon[1]), and then considers the elements for proactively transforming the field with its complexity.