Digital assistants like Siri and chatbots on messaging platforms could help brands interact directly with customers at scale. However, usability tests found that people expect assistants to have high conversational abilities and include the brand in responses. Behavioral analyses showed most assistant queries are brief, fact-based questions rather than open conversations. Facebook brand page analysis found many customer posts go unanswered and interactions can include complex conversation chains. A chatbot prototype had success with structured surveys but struggled with open-ended conversations that people often abandoned quickly. While chatbots offer opportunities, the complexity of managing open-ended conversations means early brand bots will likely focus on structured, succinct exchanges.