Ontologies are commonly used to support application tasks such as natural language processing, knowledge management, learning, browsing, and search. Literature recommends considering specific context during ontology design, and highlights that a different context is responsible for problems in ontology reuse. However, there is still no clear direction for ontology design in engineering for a variety of different contexts expressed through contextual parameters, e.g., what kind of design will better serve specific users performing a specific application task in a specific domain? There is an inbuilt connection between ontology design during ontology engineering and ontology quality. For design to determine quality, we need to first assess quality to inform design. Ontologies are described through characteristics. Context is described through parameters. These studies investigate the relationship between ontology characteristics and context parameters in order to support guidance for ontology design for a specific context. We compare the impact of a change in ontology characteristics in a lightweight ontology on the performance of novices versus experts completing a search application task in the medical domain. We propose a methodology that associates ontology design through ontology characteristics with context parameters in order to evaluate their combined performance. We use Path Selected and Guidelines Selected as the objective performance metrics. The results show a significant negative difference in performance for a medical search application task completed by novice residents and nursing students due to a change made to the ontology's structural characteristics that impact expertise and no significant difference for expert residents and nursing students. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]