New Zealand forestry has the highest number of accidents and fatalities than any other NZ industry. Worker fatigue, work environment, and worker demographics all contribute to these high numbers. We have been investigating ways of tackling these problems using wearable and sensor-based technology. Two of the challenges faced by this project are: the personal nature of data collected by wearable technology and the lack of regular access to workers to take part in user-centered design activities. In this paper, we describe the use of Lean UX methods with proxy participants and proxy technology to explore key aspects of a proposed technical solution. We show that from these experimental studies, we were able to draw appropriate conclusions on which to base the development of a prototype designed to support forestry worker safety.