In models of reflection in previous research, individual reflection processes have been considered, yet methods to support reflection and encourage learning among subordinates have not been examined. On the contrary, in manager coaching research, coaching behavior for reflection support has been examined, but the process of reflection support has not been clarified. To address these gaps, this paper aims to examine the research question, “What is the process by which a manager supports experiential learning centered on reflection to encourage the growth of his subordinates?”. Interviews of 17 managers who possessed advanced subordinate skills were conducted, and the process of experiential learning support centered on reflection was qualitatively analyzed using the grounded theory approach. The results show that experiential learning assistance consists of “preparing growth assistance,” “assigning work,” and “assisting with reflection.” In the “preparing growth assistance” , managers collaborate with mid-level employees and strive to build teams that encourage free dialogue and cooperation among members in order to psychologically reassure their subordinates. In addition, to prepare for assigning challenging works to subordinates, managers carefully observe their subordinates and gain an understanding of their career visions, characteristics, and strengths. In the “assigning work” , managers provide their subordinates with stretch experiences, which is necessary to encourage them to reflect. When doing so, they express the meaning of and expectations for the work and provide concrete guidance to improve their subordinates’ acceptance for working on the stretch assignments. In the “assisting with reflection” , managers check the facts about the experience of their subordinates strove towards and assist them in analyzing the operations. Then, they distill lessons from what they learned. This paper contributes to the existing literature by identifying the process of reflection-based experiential learning assistance, which has been insufficiently examined so far, from the viewpoint of preparing growth assistance, ensuring psychological safety, and assigning work.