Educators have many job descriptions. One of those descriptions includes the idea of customer service or professional communication, especially when engaging in difficult conversations. Difficult conversations are conversations that may be argumentative, combative, or otherwise contentious in some way. Every educator has or will have difficult conversations in their professional life. The difficult conversations may be with a family member, a student, a colleague, or an administrator. Regardless of the person, difficult conversations can influence relationships. While the idea of difficult conversations originated in the business profession, difficult conversations are also applicable and abundant in the field of education. Therefore, developing a toolkit of resources and strategies to engage in professional conversations with various stakeholders is imperative and the goal of this book. Throughout the toolkits introduced in this book, real-life examples and reflection questions are inserted. Overall, this book moves from defining difficult conversations, understanding the unconscious reactions to difficult conversations, and the tools to build positive relationships through communication.