The Forest Service has declared its intention of becoming a learning organization. As a means to that end, the Forest Service has borrowed and adapted the staff ride concept from the military. This paper describes the staff ride product and compares it to what scientific research tells us about the nature of learning. Focus group sessions were conducted to ascertain the strengths and weaknesses of staff rides. This research is intended to provide a scientific and argument basis for the digitalization of the staff ride environment for a particular organization. As such this thesis is as much a design document as it is a piece of empirical research. Designing "into the future" especially for the Forest Service's requirement, requires designing for an organization whose learning and organizations needs are quite broad and sometimes contradictory. Further sorting out of real world teaching events like the staff ride that should be transferred to digital environment at this point in time rests more on intuition than science.