A chatbot works in a couple of ways: set guidelines and machine learning. A chatbot that functions with a set of guidelines in place is limited in its conversation. It can only respond to a set number of requests and vocabulary, and is only as intelligent as its programming code. An example of a limited bot is an automated banking bot that asks the caller some questions to understand what the caller wants done. The bot would make a command like “Please tell me what I can do for you by saying account balances, account transfer, or bill payment.” If the customer responds with "credit card balance," the bot would not understand the request and would proceed to either repeat the command or transfer the caller to a human assistant.
There is no one right answer to this question, as the best solution will depend upon the specifics of your scenario and how the user would reasonably expect the bot to respond. However, as your conversation complexity increases dialogs become harder to manage. For complex branchings situations, it may be easier to create your own flow of control logic to keep track of your user's conversation.
Oftentimes, brands have a passive approach to customer interactions. They only communicate with their audience once a consumer has contacted them first. A chatbot automatically sends a welcome notification when a person arrives on your website or social media profile making the user aware of your chatbots presence. This makes you seem more proactive, thus enhancing your brand's reputation and can even increase interactions, having a positive effect on your sales numbers, too.

“Utility gets something done following a prompt. At a higher level the more entertainment-related chatbots are able to answer all questions and get things done. Siri and Cortana you can have small talk with, as well as getting things done, so they are much harder to build. They took years and years of giant company’s efforts. Different companies that don’t have those resources, like Facebook, will build more constrained utility bots.”

ELIZA's key method of operation (copied by chatbot designers ever since) involves the recognition of clue words or phrases in the input, and the output of corresponding pre-prepared or pre-programmed responses that can move the conversation forward in an apparently meaningful way (e.g. by responding to any input that contains the word 'MOTHER' with 'TELL ME MORE ABOUT YOUR FAMILY').[9] Thus an illusion of understanding is generated, even though the processing involved has been merely superficial. ELIZA showed that such an illusion is surprisingly easy to generate, because human judges are so ready to give the benefit of the doubt when conversational responses are capable of being interpreted as "intelligent".

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