In the U.S., the majority of construction companies are small companies with 10 or fewer employees (BLS, 2004). The fatality rate in the construction industry is high, indicating a need for implementing safety training to a greater extent. This research addresses two main goals: to make recommendations and design a safety training system for small construction companies, and to use Contextual Design to design the training system. Contextual Design was developed by Holtzblatt (Beyer and Holtzblatt, 1998) in an effort to address the challenge of designing new systems. Ethnographic in nature, the Contextual Design methodology requires field data collection, requirements analysis, model building, visioning and story boarding, and prototyping. A sample of 12 participants consisting of 7 tradespersons, 3 forepersons, and 2 owners/ managers, was selected for data collection. The data was analyzed based on the Contextual Design approach and a training system prototype was designed. The results of this study are recommendations for safety in small construction companies, a low fidelity paper prototype of the training system, and recommendations on future use of Contextual Design for developing training systems.