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When Bots Fail At
Conversation
“You will message businesses just
like messaging a friend!”
The Promise Of Chatbots!
Reality Check
Bots fail at conversation. A lot.
This is this primary mode of
interaction in messaging
Buttons can guide a conversation
But the expectation has been set
that people can chat like friends.
What can you
do about it?
Get Creative With Fallback
Messages
1
Consider multiple fallback messages and rotate them so
that any misunderstanding doesn’t seem like
messaging’s equivalent to an “Error 404”.
Gracefully Refocus Users
2
Serve up two messages in succession. The first is the
fallback message to the misunderstanding and
the second is a reminder of the context
Tastefully Redirect Users
3
Tell the user right at the beginning of a conversation that if
they get stuck they can always just ask for help. Remind
the user when the conversation takes an unexpected turn
Forward Users To Live Agents
4
Ask the user if they would like the bot to escalate the
request. and if they concur, funnel the user into another
response system and minimize the risk of losing them
Be Upfront
5
Be upfront about your bot’s capabilities when you first
initiate conversation and include gentle reminders when
the conversation takes an unexpected
Be Helpful
6
If users are going to go off topic, link them to 3rd party
sources that match their query. These little details can
be unexpected and delightful.
Delight Your Users.
Bots Are The Future.
Josh Barkin is Co-founder and CEO of Wordhop
Follow him on Twitter / Medium / Product Hunt
@joshbarkin

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When Chatbots Fail At Conversation