In this episode of the Think Fast, Talk Smart podcast, Matt Abrahams interviews Sheila Heen, a lecturer at Harvard Law School and expert in difficult conversations and feedback. They discuss strategies for overcoming anxiety related to difficult conversations by reframing the purpose as understanding rather than convincing, and by acknowledging the costs of avoiding the conversation. Sheila emphasizes understanding underlying emotions and assumptions, managing one's own story, and starting conversations from a third-party perspective to avoid feeling stuck. The conversation shifts to feedback, highlighting the importance of understanding the type of feedback being sought or given (appreciation, coaching, or evaluation) and ensuring clarity through dialogue and specific examples. Sheila also shares insights on navigating ongoing conflicts, especially within families, and offers advice on effective communication, emphasizing the importance of recognizing the degrees of difficulty based on the topic's importance, its impact on identity, and the potential consequences of the outcome.