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This first-person action-oriented thesis explored the primary question: “How can I increase my dialogic skills and abilities in uncomfortable conversations to help maintain and build relationships through open dialogue?” To explore boundaries and judgments within myself and with others, I framed the research in critical heuristics systems and a theory of boundary critique. I also applied an appreciative lens throughout inquiry questions and discussions with participants. Data came from self-reflective journaling sessions, one-on-one interviews with well-known subject matter experts, as well as reflective, and sometimes uncomfortable conversations with feedback partners. The research adhered to the Royal Roads University Research Ethics Policy. Findings showed that I had skills and competencies in uncomfortable conversations and showed how I can improve through continued learning. Five findings, five conclusions, and four recommendations came from this thesis. An appreciative lens is critical. Some recommendations may be of value to other practitioners and organizations.
Keywords: uncomfortable conversations, boundary critique, critical heuristics systems, personal mastery, unconscious bias, diversity, equity, inclusion, dialogue, systems thinking, confidence, digital journaling.