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Challenge #2: Conversational Intelligence

What’s the right interface for an AI tool that initiates conversations, yet gives users full control over their plans?


Solution:
Two tabs that share the same trip data, but serve different contexts. Timely suggestions appear in chat, while strategic suggestions appear inline in plan. Actions in one tab update the other.

Chat Tab (Tactical)
  • Real-time AI chatbot
  • AI initiates most conversations
  • Quick reply buttons, text or voice input

Plan Tab (Strategic)
  • Visual itinerary with day/time structure
  • Inline AI suggestions
  • Drag-and-drop editing


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