Abstract. In practice, digital transformation and ESG principles are being implemented in parallel, but their integration is hampered by the lack of tools capable of accounting for the dynamics of technology and knowledge obsolescence. Existing approaches are fragmented and static: they capture the "here and now" state, ignoring the growing cognitive-temporal gap – the discrepancy between the rate at which new solutions emerge and the organization's ability to absorb them. The goal of this paper is to fill this gap by proposing a diagnostic tool for assessing the integration of these two processes at the organizational level. The methodological basis is a critical analysis of existing approaches and a theoretical synthesis of the concepts of temporality and organizational learning. As a result, two interconnected tools were proposed. A dual-axis diagnostic and prognostic matrix, built at the intersection of structural-functional and temporal dimensions, enables the positioning of initiatives by primary focus (technological, process-managerial, socially-oriented) and forecasting their resilience to obsolescence based on their classification as conservative, adaptive, or proactive. The "Methodological Gap Map" operationalizes the concept of a cognitive-temporal gap, establishing cause-and-effect relationships between operational symptoms (strategic, communication, and competence gaps), their underlying causes, the risks they generate, and decision vectors. The scientific novelty lies in the operationalization of the principle of anticipatory adaptability and the conceptualization of the cognitive-temporal gap as a systemic organizational barrier. The practical significance lies in providing managers with structured tools for auditing current projects, making informed strategic choices, and proactively managing integration processes, thereby reducing the risk of ineffective investments and increasing the organization's adaptability over the long term.