This paper explores the connection between mental structures shaped by past events and managerial action targeted to manifest an uncertain future and does so in the light of artificial intelligence (AI). By drawing on predictive brain theory, the paper conceptualizes that prospective sensemaking is increasingly required for managers. To shed light on prospective sensemaking in uncertain times, we draw on the concept of network pictures to conceptualize managers’ sensemaking and consequent actions based on the notion of companies being embedded in a context (network) affecting strategies and their outcome. The network pictures managers form through sensemaking reflect the presence or the past, but what happens when we take the notion of a future that is inherently different from the past as the guiding light for present actions seriously? The paper contributes to research by extending the network picture concept and interlinking it with neuroscience and specifically AI as a motor of change, and as challenging the human thought with machine learning