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People have a hard time talking about difficult topics. This work details how spaces and things play an active role in conversation and can help people better direct their conversation toward deeper engagement, sharing and discussing ideas and experiences that pertain to the problem at hand. Conversations are the medium through which people collaboratively deliberate, or together, make sense of complex situations. Conversation can be defined as two or more people talking together. Within this broad scope exists a special subtype that I call the high-stakes conversation. A high-stakes conversation occurs between an expert and a client when the client is engaged in planninga course of action in a complex situation. High stakes conversations are, in a sense, a new architecture of place that has continually evolving sets of mores for behavior.This research shows the high-stakes conversation has five essential characteristics. The first, and most significant, is that dialog centers around making a decision of consequence. Additionally, in this dialog: there is no���right��� answer, a decision is imminent, participants are characterized by imbalances in knowledge, power, experience and consequence, and decisions are irrevocable. Another special subtype of conversation, identified by Stone, Patton and Heen (2010), is the difficult conversation. Difficult conversations occur when aspects of the participants��� identity become at stake in the conversation. Over the course of four years of research and fieldwork I have documented some understandings of how things (images, spaces, objects, and interfaces) can function in facilitative ways in high-stakes and difficult conversations.This work investigates conversation as shaped by deliberative democracy protocols, facilitated by games, in high-stakes and difficult conversational contexts. Fieldwork principally consisted of planning, designing artifactsfor, conducting, and facilitating a variety of meetings on different topics, in different environments, approaching a broad array of problems. Through this research, I argue that things, the metaphors things evoke, and the systems that surround, play a significant role in constituting theconversational environment ��� that things are active as facilitators in the conversational field and should be created with respect to that framing to elicit a more convivial, generative experience.