" Is my enterprise secure ? " has always been difficult to answer through Red Team Assessment, as organizations often only address short-term issues without integrating them into long-term cybersecurity strategies. In this presentation, we will examine the challenges faced by enterprises based on observations from nearly a hundred red team experiences and reflect on past issues. To address this, we will introduce a new approach to structuring red team outcomes, like placing axes on the battlefield, to help enterprises overcome the dilemma of solving short-term problems separately and effectively leverage the full benefits of Red Team Assessment.