In this paper, we discuss how taking a speculative feminist approach, as proposed by some members of the human-computer interaction (HCI) community, results in a radically different design of software for project management. As we interpret it, speculative feminist design in HCI demonstrates attention to the following six principles: challenging the status quo; designing for an actionable ideal; searching out the invisible; considering the micro, meso, and macro; privileging transparency; and welcoming critique. In the context of project management, our approach to software design has therefore included the following priorities: all stakeholders have goals, but not necessarily shared goals; the line between an internal deliverable and an external project outcome is blurred; impacts can occur immediately or decades later; impact assessment methods need to be explicit in the project planning system. In adopting the terms speculative feminism and critical feminism, we intend that our work be understood as situated within the territory of Critical Theory as applied particularly to the work of the Frankfurt School. We introduce our design, called It’s a Wicked World (IWW), as an example, although it is only the current iteration of one part of a larger, ongoing project.