There is a growing interest in socially engaged engineering, which emphasizes the consideration of social, cultural, environmental, and economic factors to broadly benefit society. However, current workforce training and engineering education programs do not adequately support skill sets needed to link complex societal needs and contexts to design processes. Effective stakeholder-facing communication skills and designer-facing reflective skills are needed for engineers to assess stakeholder needs, design contexts, and their own approaches as designers. These challenges are made more difficult when design is done across distance and socio-cultural differences, which is increasingly common due to remote communication and design technologies. A lack of preparation in these cases can lead to ineffective or even harmful designs, especially if effective socially engaged practices are not incorporated early in design processes during problem identification, problem definition, requirements development, and initial concept generation. Despite these complexities and persistent evidence of ineffective design solutions, engineers continue to engage in ways that imply they can navigate design work objectively and apolitically, assuming good intentions and technical skills compensate for gaps in broader understanding. This dissertation focuses on two key, understudied skills for early stages of socially engaged design: stakeholder engagement with prototypes in remote design contexts, and designers' reflective considerations of the impacts of their positionalities and other stakeholders' positionalities on design decision-making. The first study explores strategies for remotely engaging project stakeholders with prototypes through semi-structured interviews with engineering ten students and ten practitioners. The second and third studies explore conceptions of the roles of identity and positionality in design for 'social good' contexts through an exploratory, interview-based study of five undergraduate students and a larger, interview-based study of ten undergraduate students and ten practitioners. Regarding remote stakeholder engagement with prototypes, student and practitioner participants reported overlaps between many in-person and remote approaches, as well as strategies for adapting to remote engagements. Four distinct strategies tailored to remote engagements emerged from the findings including the use of third-party, in-person facilitators and various ways to share digital and physical prototypes asynchronously. Participants also discussed implicit consideration of stakeholder identities, such as age and professional position, in selecting appropriate strategies, and reported learning these skills on the job rather than through formal education. While student participants discussed mixed perceptions of the effects of remote engagement on design outcomes, practitioners described remote, hybrid, and in-person engagements as equally effective, highlighting gaps between student and practitioner skill sets. The studies of designer conceptions of positionality revealed that even among participants with personal interest in identity and positionality in design, conceptions were self-reported as implicit and limited by a lack of language and free discussion within engineering design communities. Participants also cited exposure to differences in identities and contexts, many of which came from their personal lives outside of design work or education, as driving the development of their conceptions of positionality. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]