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The architecture, engineering, and construction (AEC) industry globally has a long history of prudently adopting novel technologies to improve products and services. Yet the rapid development of digital technology currently taking place is threatening to produce a more disruptive inflection, or substantial jolt. This paper explores the state of readiness of the AEC industry for such anticipated transformation. We illustrate our conceptual arguments with evidence from an explorative study across a sample of AEC organizations in Australia. At the core of this paper, we offer six provocations that highlight what we consider major challenges for the AEC industry-across multiple levels of analysis-related to the increasing role of digital technology. We then turn to lessons learned from other industries in order to propose a framework consisting of four leadership thinking schemas to enable digital transformation readiness: future thinking, strategic thinking, capability thinking, and experimental thinking. For these four schemas, we present practices and initiatives that may help AEC firms to better adapt-or to proactively create and shape a sustainable future.