Artificial intelligence (AI) is fundamentally reshaping classroom experiences. In this activity, students in a graduate-level project management class engaged in real-time conversations with AI- powered chatbots as though they were actual people. Students were required to perform a stakeholder analysis on the key stakeholders involved in their project. This analysis was the first step in developing the communication management plan as a component of the project management plan required to execute the project. To execute this student experience, the instructors built artificial intelligence-powered chatbots by utilizing a free online chatbot character generator located online at www.character.ai to interact with students as though they were actual people. These interactions provided a rich student experience with improved depth of interactions as opposed to the traditional stakeholder analysis methods. Ultimately, in this case, the instructors argue that interactions with AI-powered chatbots enrich student learning and foster critical thinking by providing a more authentic experience. Courses: Small-group, business, project management, professional, and organizational communication. Objectives: By the end of this activity, students will be able to (1) perform a stakeholder analysis on an individual to determine the most effective frequency and mode of communication; (2) identify interpersonal dynamics of the individual of interest, such as their power, influence, and authority relative to their project; and (3) describe interpersonal conflicts between the AI-powered individuals to inform the communications management plan.