ELIZA, one of the first chatbots ever built, was introduced more than 50 years ago, but it was not until Siri in 2011, Alexa in 2015, and Facebook’s Bots launch in 2016 that we saw anything close to mass market adoption of conversational assistants. As with these applications, most technologies that start in the consumer world eventually reach the commercial enterprise, but should chatbots be treated as traditional projects? Chatbots are essentially ushering in a new era of man-machine interaction—one that goes far beyond the now familiar “information retrieval” applications that rely on simple question-answer system constructs. As machines are starting to learn how to speak and to perform traditionally human functions, should we treat them more like humans? This is a new IT frontier. Is the goal to improve the human condition? These and other similar questions must be asked, but here is the big question: How do enterprises get this right?