Existing literature on expatriate managers tends to focus on their adjustment from the point of view of individual well-being. This article, in pointing out that international assignments are an opportunity to internationalize the company through a learning process, has a different emphasis. Japanese companies tend to employ many Japanese expatriate managers in overseas locations. The development of cross-cultural adaptation among expatriate Japanese managers in two retail subsidiary companies in Hong Kong was studied. In both companies, the expatriates learned reactively rather than proactively, so that either zero or single-loop organizational learning ensued for the parent company. The reactive learning approach stemmed from expatriates perceiving that their career prospects related more to events back at the parent company than to the success or failure of the local subsidiary, and that it might be harmful to their career if they internationalized themselves during the overseas assignment.