To understand central problems in making chatbots, this project uses analogous observation, expert interviews, and theoretical analysis, uncovering connections between conversation and trust. This research suggests designing for dialogue, personality, and conversational structure in order to create trustworthy chatbot experiences. The resulting collaborative methods are Improv, Bot Personas, and Conversation Mapping. These prototype design methods were iterated and tested over three workshops held with digital professionals. Bot Personas and Conversation Mapping proved to be very effective, while Improv remains imperfect.