In technically challenging and safety critical work, the primary objective in software design should be supporting execution of that work. Here, experienced usefulness may be the primary contributor to a good “user experience”. We report two successful case studies assessing work-needs and designing software; both support planning and scheduling. Case 1 addresses software for planning the movement of the International Space Station (ISS). Case 2 addresses software for planning airlift operations. We compare the processes and representations in the two projects and offer a few suggestions about their benefits.