The allure of chat bots has grown among L&D professionals as the promise of artificial intelligence appeals to teams asked to do more with training their people. Yet, as with any emerging technology, the promise of 'better and faster' can often fall flat with unforeseen obstacles and operational clumsiness. This session will review chat bot design principles, including personality, timing of interactions, program types, personalization and messaging options, handling mistakes, and ideal staffing for chat bot projects. The ability to drive learner accountability and reinforcement makes the chat bot an ideal tool---if done well! This session was recorded at the ATD 2019 TechKnowledge conference in West Palm Beach, Florida.