Digital technologies permeate and transform organisational practices. As a society, we need means to explore the uncharted terrain that lies ahead and the desirability and consequences of possible courses of action to move forward. We investigate a design approach, called ‘future probing’, to envision and critically analyse possible futures around digital technologies. We first reconstruct our journey and describe related insights on the process, content and context level. Reflecting on the journey, we then extract a key insight revolving around the challenge for participants to link back from exploring the future to their present practice. In a first attempt at theorizing these difficulties, we see future probing as a practice that opens up adaptive space (Uhl-Bien & Arena, 2017) in which people from different backgrounds engage in dialogue about possible futures of digital technologies. We found that adaptive processes, like semi structuring, temporary decentralisation, and collaboration (Uhl-Bien & Arena, 2018) were supported by the future probing practices and seemed to create space for employees to engage in exploration. There was still a lack of compelling acts of brokering and network cohesion (Uhl-Bien & Arena, 2018). This may indicate why linking back to daily practice is challenging. We assume that organising for adaptability requires a deliberate act of connecting far future explorations with present action, and propose that besides explorative skills, ‘adaptive anticipating’ action is needed to make the connection and that linking back through near future experiments might be a way to achieve this.