AI-Enhanced Conversation Design for Airbnb Search
Adedayo Agarau
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Posted Dec 21, 2025
Speculative AI conversation design to enhance Airbnb's search experience.
Airbnb AI Case Study
A speculative conversation design and content strategy case study for AI-mediated messaging in Airbnb's search experience.
Project Overview
This case study reimagines Airbnb's search experience using AI-powered conversational interfaces. Based on CEO Brian Chesky's November 2024 announcement about AI search features, I developed a comprehensive conversation design system that demonstrates how AI could mediate communication between guests and the platform.
What's Included
Complete System Design (~50 pages)
4-layer conversation architecture (routing, understanding, generation, safety)
11 complete dialogue flows covering common and edge-case scenarios
XML-formatted system prompts with safety guardrails
Decision trees for handling clarifications and ambiguity
Microcopy Guide (200+ examples)
All UI strings, error messages, and success states
Character limits for web, mobile, and voice interfaces
Voice & tone guidelines for AI personality
Platform-specific content variations
Skills Demonstrated
Conversation design for multi-turn AI dialogues
System prompt engineering with production-grade safety considerations
Content strategy across multiple platforms and modalities
Systems thinking for scalable AI architecture
Honest production assessment including gaps and next steps
Methodology
Real foundation:
CEO announcement of AI search features
Personal testing of current Airbnb search limitations
Competitive analysis and user feedback research
My design work:
Independent interpretation and system design
No internal Airbnb data or validation
Speculative but evidence-based approach