Project management (PM) and systems engineering (SE) are essential skills in information technology (IT). There is an abundance of information available detailing the comprehensive bodies of knowledge, standards, and best practices. Despite the volume of information, there is surprisingly little information about how to tailor PM and SE tasks for small IT projects. Small projects cost between $5,000 and $1.5M and range from three to twelve months in duration. (Kerzner, 2009) The goal of this research has been to extract heuristics from the PM and SE experts and literature to better understand and quantify required tasks, develop and verify tailoring methods, build the methods into an expert system, and test the expert system with novice users to determine the effectiveness of the tailoring methods and the expert system. Research has been conducted to add new methods to help project managers effectively plan and manage small projects. [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.]