In this opening article, the author describes the background of this special issue. Our modern society has two different kinds of aspects; an advanced technology society aspect and a future co-creation oriented society one. Under the circumstances, there is a need for considering how organizations manage their members’ trial and error behaviors to achieve innovation. Based on literature survey in management studies including learning theory, creativity theory, and organizational management, this article defines the trial and error behavior as a process of knowledge exploration by randomly taking action, getting results, creating insights, learning, and making change of inertia. The aims of this article to consider how the trial and error behavior can be affected by two aspects of modern society. After considering reality and potential of artificial intelligence technology as one of the advanced technologies, the author suggested the importance of thinking about collaborative relationship with its technology in doing trial and error. This article also mentions about how we should have an attitude to trial and error in collaborative innovation under multi-stakeholder context.