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Generative AI technologies have opened new possibilities for enhancing students' reflection and self-awareness. A GenAI-powered chatbot, "Professor E," provides students with instant feedback and deepens their learning and reflection as a virtual instructor. This study explored how 32 undergraduates leveraged the chatbot to generate personalized prompts, questions, and narratives that encouraged deeper introspection and self-analysis in a social innovation and entrepreneurship course. Analysis of student-AI dialogues revealed that this reflective process enhanced students' knowledge and reflection capacities. However, students needed AI literacy skills, such as prompting techniques, as well as the ability to share detailed thoughts, feelings, and experiences for more relevant recommendations. The findings highlight the potential for GenAI to foster personal growth, knowledge, and skill development through human-AI collaboration.