Digital assistants and chatbots have the potential to connect brands directly with large numbers of consumers through popular messaging platforms. However, three experiments showed that (1) people expect voice assistants to have brief, accurate responses rather than lists of links, (2) individual messenger conversations are usually brief while long conversations can be complex, and (3) early chatbot prototypes struggled with open-ended conversations but worked better with structured surveys. To become a "brand's best friend," chatbots may initially focus on subtle, background roles rather than attempting complex open conversations.