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.

Ultimately, only time will tell how effective the likes of Facebook Messenger will become in the long term. As more and more companies look to use chatbots within the platform, the greater the frequency of messages that individual users will receive. This could result in Facebook (and other messaging platforms) placing stricter restrictions on usage, but until then I'd recommend testing as much as possible.
Chatbots have come a long way since then. They are built on AI technologies, including deep learning, natural language processing and  machine learning algorithms, and require massive amounts of data. The more an end user interacts with the bot, the better voice recognition becomes at predicting what the appropriate response is when communicating with an end user.
Developed to assist Nigerian students preparing for their secondary school exam, the University Tertiary Matriculation Examination (UTME), SimbiBot is a chatbot that uses past exam questions to help students prepare for a variety of subjects. It offers multiple choice quizzes to help students test their knowledge, shows them where they went wrong, and even offers tips and advice based on how well the student is progressing.
It’s best to have very specific intents, so that you’re clear what your user wants to do, but to have broad entities – so that the intent can apply in many places. For example, changing a password is a common activity (a narrow intent), where you change your password might be many different places (broad entities). The context then personalises the conversation based on what it knows about the user, what they’re trying to achieve, and where they’re trying to do that.
Using this method, you can manage multiple funnels of content upgrades, and even convince your users to take the next step in the buyer journey directly within Messenger. In the example below I just direct the user to subscribe to content recommendations via Messenger, but you could push them to book a meeting with a sales rep, take a free trial or directly purchase your product.

This kind of thinking has lead me to develop a bot where the focus is as a medium for content rather than a subsitute for intelligence. So users create content much as conventional author, (but with text stored in spreadsheets rather than anywhere else). Very little is expected from the bot in terms of human behavious such as “learning”, “empathy”, “memory” and character”. Does it work?

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As AOL's David Shingy writes in Adweek, "The challenge [with chatbots] will be thinking about creative from a whole different view: Can we have creative that scales? That customizes itself? We find ourselves hurtling toward another handoff from man to machine -- what larger system of creative or complex storytelling structure can I design such that a machine can use it appropriately and effectively?"
A chatbot (also known as a talkbots, chatterbot, Bot, IM bot, interactive agent, or Artificial Conversational Entity) is a computer program or an artificial intelligence which conducts a conversation via auditory or textual methods.[1] Such programs are often designed to convincingly simulate how a human would behave as a conversational partner, thereby passing the Turing test. Chatbots are typically used in dialog systems for various practical purposes including customer service or information acquisition. Some chatterbots use sophisticated natural language processing systems, but many simpler systems scan for keywords within the input, then pull a reply with the most matching keywords, or the most similar wording pattern, from a database.
With competitor Venmo already established, peer-to-peer payments is not in and of itself a compelling feature for Snapchat. However, adding wallet functionality and payment methods to the app does lay the groundwork for Snapchat to delve directly into commerce. The messaging app’s commerce strategy became more clear in April 2016 with its launch of shoppable stories with select partners in its Discover section. For the first time, while viewing video stories from Target and Lancome, users were able to “swipe up” to visit an e-commerce page embedded within the Snapchat app where they could purchase products from those partners.
However, the revelations didn’t stop there. The researchers also learned that the bots had become remarkably sophisticated negotiators in a short period of time, with one bot even attempting to mislead a researcher by demonstrating interest in a particular item so it could gain crucial negotiating leverage at a later stage by willingly “sacrificing” the item in which it had feigned interest, indicating a remarkable level of premeditation and strategic “thinking.”
On the other hand, early adoption can be somewhat of a curse. In 2011, many companies and individuals, myself included, invested a lot of time and money into Google+, dubbed to be bigger than Facebook at the time. They acquired over 10 million new users within the first two weeks of launch and things were looking positive. Many companies doubled-down on growing a community within the platform, hopeful of using it as a new and growing acquisition channel, but things didn't exactly pan out that way.
Jabberwacky learns new responses and context based on real-time user interactions, rather than being driven from a static database. Some more recent chatbots also combine real-time learning with evolutionary algorithms that optimise their ability to communicate based on each conversation held. Still, there is currently no general purpose conversational artificial intelligence, and some software developers focus on the practical aspect, information retrieval.
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