Teachers play a key role in communicating with parents to support student learning. One of the more challenging aspects of this role for teachers is having a difficult conversation with a parent about their child. Difficult conversations, when needed, are best accomplished face-to-face incorporating effective communication skills to promote a positive and productive interaction. This article reviews a number of key practical communication skills that teachers can use when communicating with parents including use of clear vocabulary, active listening, I-messages, questioning strategies, paraphrasing and summarizing, leveled information, as well as attention to nonverbal messages. Strategies to support both planned and unplanned difficult conversations are discussed. Barriers to having difficult conversations between teachers and parents are outlined as well as new directions for research. Effective communication skills are integral for teachers to hold difficult, yet productive, conversations with parents to promote partnerships and to support student success.