The Automation Checklist

This checklist is a phased roadmap that takes you from zero to around 95% automated guest communication. Each phase raises the share of messages the AI can handle without your team, and each item links to a detailed guide on how to do it.

Work through the phases in order — each one builds on the one before. You can check items off as you complete them, and your progress saves on your device, so you can pick up exactly where you left off.

How to use this checklist

Go through the phases from top to bottom. Don't skip ahead — the later phases assume the earlier ones are done (for example, per-listing rules are far easier to write once your listing details are complete).

Each item links to a guide that explains what to do and why. When an item is done, tick it off. You don't need to finish everything in one sitting; the checklist is designed to be worked through over a few sessions.

Phase 1 — Foundation

Target: around 70% of routine questions auto-replied. This phase is about giving the AI the raw material it needs to answer everyday guest questions.

• Complete your Your Space details in the listing — property type, capacity, amenities, and descriptions.
• Complete the Arrival Guide — house rules, check-in method, wifi, location, directions, and house manual.
• Turn on Smart Reply so the AI responds to incoming guest messages automatically.
• Add your first workspace rules covering your most common policies.
• Set the AI's tone so every reply sounds like your brand.

Phase 2 — Optimization

Target: around 85% auto-replied. This phase tunes the AI for the specifics of how you run your property.

• Add per-listing rules for anything unique to a single unit (shared pools, specific parking, quirky access).
• Review behavior settings — response delay, unknown amenity handling, and check-in/check-out handling.
• Teach the AI new facts through chat as you notice questions it couldn't answer.
• Set up room-ready notifications so the AI can confirm a unit is ready before guests arrive.

Phase 3 — Full Automation

Target: around 95% auto-replied. This phase is about keeping the system sharp and making your team part of the loop.

• Connect the host and staff messaging channels so handoffs reach the right people instantly.
• Train your staff on handoff replies — the #id format they use to answer tickets.
• Monitor the messages the AI still hands off and add rules or listing facts to absorb them.
• Review and prune your rules regularly so the AI never works from outdated policies.