Tough Conversations

Tough Conversations is a browser-based application designed to help individuals prepare for difficult discussions across personal and professional contexts. It addresses the challenge of navigating hard conversations by offering evidence-based techniques that are tailored to the user's specific situation. Users are prompted to describe the context and dynamics of their upcoming conversation, with the option to focus on interactions with partners, colleagues, bosses, clients, or others.

The tool organizes its support into four key areas: emotional self-management, preparing the conversation, handling the conversation in the moment, and achieving a clear outcome. Each area contains multiple techniques—fifteen in total—drawing from research and frameworks such as the Harvard Negotiation Project, the NeuroLeadership Institute, Nonviolent Communication, and Mindfulness-Based Stress Reduction. After users specify where they need the most help, the platform selects an appropriate evidence-based framework and uses Claude (Anthropic's AI) to generate personalized advice, including actionable steps and suggested language. Users can explore different techniques, request more examples, and build a personalized Help Kit, which can be saved or printed as a PDF for reference.

Tough Conversations runs entirely in the user's browser, with privacy emphasized: the details of each situation are sent only temporarily to Claude for the purpose of generating tailored tips, and no information is stored or shared. No account is required to use the service. 0 license, and it is part of the Org360 Assessment Suite. Its approach is grounded in established research, aiming to support the full arc of challenging conversations from preparation to resolution.