The purpose of this paper is to define and explore the immediate and long term effects and the resulting organizational dynamics of advancing technology on maintenance workplace expertise in transportation. In the past ten years the face of maintenance in the transportation workplace has completely changed as computerization has taken over the control of transmissions, engines, and bus/truck environmental systems and transformed them from "closed" stand alone components to an interdependent "open system" in a state of constant communication. The immediate future brings with it the advanced technology of the Intelligent Transportation System with its Geographic Information System, in-vehicle logic system, automated annunciation, signal prioritization, global positioning, and live audio and visual data links with a central control center. This complexification of the transportation maintenance workplace is being compounded by the growing use of alternative fuels, and the resultant requirement for the maintainer to learn a new operational set of skills and competencies. This evolution of technology in transportation has caused a revolution in technical training/or which the maintainers of transportation resources must reskill immediately to meet the demands of the technology invasion. The paper examines the need for an accelerated evolution of workplace expertise using a combination of motor skill and cognitive training competency based learning techniques to evolve the maintainer through the phases of basic operation, to systems expert, to system creator. This evolution is accomplished through the use of a four step implementation strategy which begins with the determination of training sources, the development of an effective resource investment strategy, the development of a model trained cadre, and concludes with the expansion of this model to improve the overall baseline of workplace expertise.