This episode explores the art of asking purposeful questions in professional settings, particularly focusing on how to improve this skill to enhance executive presence and career advancement. The discussion centers on Megan, a program manager seeking to develop more strategic questioning skills. Against the backdrop of Megan's experiences—one successful question leading to team applause and another unsuccessful attempt that felt confrontational—the conversation delves into the complexities of communication. More significantly, Alison Wood Brooks, a Harvard Business School professor specializing in conversation, highlights the crucial difference between one-on-one and group interactions, emphasizing the increased risk of judgment and shame in larger settings. For instance, she suggests leveraging one-on-one conversations to build confidence before tackling more challenging group settings. The discussion then pivots to practical strategies for framing questions, including using open-ended "what" questions instead of accusatory "why" questions, and focusing on the goals of the conversation to guide question selection. Ultimately, the episode emphasizes the importance of embracing natural conversational styles, even if they involve "ums" and trailing off, and reframing feedback requests as forward-looking advice to foster a more collaborative and less judgmental environment. What this means for professionals is a shift from striving for perfectly formed questions to focusing on the overall pattern of questioning and the ability to engage in meaningful information exchange.