The construction industry has had difficulty adopting project management software effectively and in a widespread manner. This thesis seeks to uncover common problems preventing the adoption of new software for construction project management, and to find a method to design more successful software. Construction project managers working at universities in the state of Georgia were selected as the specific group to study. To better define the functions of project management software, as well as uncover benefits both realized and anticipated, research was conducted. A Situation Awareness based approach was selected to result in proposing a prototype application that would specifically match the mental model of the study group. To define the mental model, a Goal Directed Task Analysis method was used by way of an online survey and in-person verification. In order to collect the survey data, a web based Goal Directed Task Analysis application was created and tested as a part of this thesis. Using the survey data, a proposed design for a prototype application was proposed. The application design was specifically made to fulfill the needs of project managers like those in the study group. The GDTA method proved effective in producing a software design. Recommendations to create and test the proposed prototype application are provided as a next step.