The use of digital tools such as Sketchup, Rhino, AutoCAD and others is now commonplace in the architectural design process. These tools have advantages for time management and support the iterative nature of design, while also providing an efficient connection to later stages of design development and construction documentation. However, it could be argued that the use of digital tools during the ideation and concept phases of designing limits the cognitive connection between thought and the hand that is present in freehand sketching. If we accept that this cognitive connection is foundational to the design process, then new digital sketching tools are needed that have features similar to freehand sketching while processing sketches to 2D and 3D representations that are translatable to 3D printing, digital fabrication, and eventually Building Information Modeling. What this new tool might be is currently unclear. The purpose of this research is to identify the characteristics of a next generation of sketching tools that could support ideation activities in the concept stage of architectural design. The results will help to design a roadmap for the implementation of digital technologies in the architectural design process. This research will contribute to a shift in the implementation of digital tools in the architectural design process. This research relied on multiple data sources. First, a logical argument tactic was used to develop the research design model through a comprehensive review of the scholarly work that addresses the design process in the concept stage and the role of sketching and digital tools throughout these processes. Second, case study observation and interviews were used to explore how architects and architectural students at Virginia Polytechnic Institute and State University (Virginia Tech) use sketching, 3D modeling, and existing digital tools to represent, develop, iterate, and communicate their design ideas in the concept stage and how the tools they used affect their design process. Third, two immersive case studies were conducted to identify and develop the characteristics of a digital sketching tool. The last step was to determine consensus for the appropriateness of the To-Be model through Delphi tactics. / Doctor of Philosophy / The use of digital tools such as Sketchup, Rhino, AutoCAD and others is now commonplace in the architectural design process. These tools have advantages for time management and support the iterative nature of design, while also providing an efficient connection to later stages of design development and construction documentation. However, it could be argued that the use of digital tools during the ideation and concept phases of designing limits the cognitive connection between thought and the hand that is present in freehand sketching. If we accept that this cognitive connection is foundational to the design process, then new digital sketching tools are needed that have features similar to freehand sketching while processing sketches to 2D and 3D representations that are translatable to 3D printing, digital fabrication, and eventually Building Information Modeling. What this new tool might be is currently unclear. The purpose of this research is to identify the characteristics of a next generation of sketching tools that could support ideation activities in the concept stage of architectural design. The results will help to design a roadmap for the implementation of digital technologies in the architectural design process. This research will contribute to a shift in the implementation of digital tools in the architectural design process. This research relied on multiple data sources. First, a logical argument tactic was used to develop the research design model through a comprehensive review of the scholarly work that addresses the design process in the concept stage and the role of sketching and digital tools throughout these processes. Second, case study observation and interviews were used to explore how architects and architectural students at Virginia Polytechnic Institute and State University (Virginia Tech) use sketching, 3D modeling, and existing digital tools to represent, develop, iterate, and communicate their design ideas in the concept stage and how the tools they used affect their design process. Third, two immersive case studies were conducted to identify and develop the characteristics of a digital sketching tool. The last step was to determine consensus for the appropriateness of the To-Be model through Delphi tactics.