Most people have been stuck with a support bot that won’t let them through. I work on the opposite problem: teaching ours to notice when it should step aside.
I wrote a post on the WordPress.com blog about how it makes that call. Here’s the short version.
Before the assistant answers anything, it runs a few checks. Have you already asked for a person? Have you asked this same question before? Have you contacted support about it recently? Is this the kind of topic a bot shouldn’t handle on its own? If the answer to any of those is yes, it starts moving you toward a human instead of trying again.
It also offers a person without being asked. That happens when a problem needs someone to look into an account properly, when the assistant isn’t confident in its own answer, or when what it already suggested didn’t work.
And if you ask for a person outright, it doesn’t argue with you. It might ask one or two quick questions in case it can fix the problem on the spot, but the offer to hand over stays on the table. You choose.
The part I care about most is what happens after that. When it hands you over, the whole conversation goes with you — what you asked, what it tried, what didn’t work. Nobody has to explain their problem twice.
The number that surprised me: about one in four conversations ends up with a person, and in about half of those, the assistant is the one who suggested it. It offers first more often than people expect.
That’s the goal, really. Solve what it can. When it can’t, get out of the way quickly.
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