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The 5 Qualities of Site-Specific AI Chatbots

Handoff willingness, flexibility, proactivity, emotional responsiveness, and transparency help you build trustworthy AI chatbots that guide users well.

Georgia Kenderova, Tanner Kohler •

Summary: Handoff willingness, flexibility, proactivity, emotional responsiveness, and transparency help you build trustworthy AI chatbots that guide users well.


Designing a site-specific AI chatbot requires making key decisions even before user testing begins. The five chatbot qualities described in this article — handoff willingness, flexibility, proactivity, emotional responsiveness, and transparency — can guide those early design decisions and provide a framework for evaluating existing chatbots. (But don’t neglect real testing. Real users will help you finetune the specific behaviors that will best serve their needs.)

Getting these qualities wrong can be costly. People are still forming mental models of site-specific AI chatbots and figuring out whether to view them as human customer-support representatives or frontier-level LLMs. Many chatbots fall short of both types of expectations and quickly get abandoned by users.

1. Handoff Willingness: Respect Users' Desire to Speak with Real People

AI chatbots should allow users to connect with human agents with minimal friction.



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