We thrive when we are working and learning in environments that support our emotional well-being. These are environments in which we feel heard, valued, safe, and included. Group leaders (e.g., meeting leaders, managers, teachers) struggle to collect information about the emotional state of each of their group members, yet this information is helpful for understanding how to support their groups’ engagement, productivity, collaboration, wellbeing, and intra-group relationships. The Reflect messaging extension helps team members be more aware of their own, and each other’s, emotional state during communication by giving them the ability to create simple, effective, and engaging emotional check-ins directly in the flow of a conversation in Teams. Group leaders can check-in with their team members about how they are feeling in general, or about a specific topic, such as an assignment, the experience of learning or working from home, or current events in their community.