Abstract
Technological obsolescence creates a growing strategic leadership challenge that research has largely overlooked. Leaders must manage technologies that remain operationally essential yet steadily decline, creating long periods of strategic ambiguity, capability erosion, and investment tension. This study examines how leaders design and execute responses to obsolescence while sustaining operational continuity and organisational coherence. Drawing on theories of capability development, technical debt, replacement optimisation, and socio‑technical discontinuity, it uses a mixed‑methods approach that combines quantitative analysis of decision patterns with qualitative insights into leadership sensemaking during decline. Anticipated findings highlight the role of timing mechanisms, governance alignment, capability renewal, and strategic communication in navigating long‑tail decline. The study contributes to leadership and strategy scholarship by shifting attention from innovation acceleration to managed disengagement and renewal, offering a Technological Obsolescence Strategy framework to guide leaders facing inevitable system decline.