# Adeline Yaw — AI Engineer Sydney 2026

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Canonical page: https://webdirections.org/ai-engineer/speakers/adeline-yaw/
Program status: The speaker lineup and talk descriptions are public. Session days, times, rooms and the full timetable have not yet been published.

## Half our handoffs are the bot's idea


About one in four conversations with WordPress.com's AI support bot ends with a person. In about half of those, the bot suggested it.

These are two different problems. In one, the user asks for a person. In the other, the bot decides on its own to stop. On paid plans, when a user asks for a person, we hand the conversation to our support team with as few extra questions as we can. The two cases fail in different ways and need different fixes, but the second one gets much less attention.

This talk is about the second one, when the bot decides to stop. Our bot checks whether a conversation needs a person before it answers, not only after an answer has failed. I'll explain why it works this way and what that costs us. Then I'll cover what the bot says when it stops, and what it passes on.

## Adeline Yaw

AI Integration Specialist, Automattic

Adeline Yaw spent eight years answering questions from WordPress.com users via live chat and email. She now leads the AI Squad at Automattic and looks after the AI assistants that users talk to first. She judges them the way a support person would: did the user get the right help, and did they reach a person when they needed one?

## Conference

- [Conference overview](https://webdirections.org/ai-engineer/index.md)
- [Agent guide](https://webdirections.org/ai-engineer/for-agents/)
- [llms.txt](https://webdirections.org/ai-engineer/llms.txt)