Today I’m starting a new series of blog posts on my failed conversations with AI chatbots. I find AI to be a super interesting technology, but often rather superfluous. The AI chatbots that companies post on their websites and in their apps too often feel gimmicky to me… a good idea in theory, but in practice shallow and not useful.

When I tell people that AI chatbots almost always fail to work for me I get misconstrued. They interpret that to mean that I hate AI, or perhaps that I am denying their lived experience of AI being useful to them. That is not what I am saying! I am trying to express a factual statement that almost every time I use an AI chatbot for a task it fails me. Explaining that requires much detail and a lot of specifics, and is, frankly, a rather boring topic of conversion so I never do actually explain.

So now I am. This series documents a bunch of conversations I have had with AI chatbots, showing exactly what I wrote and explaining how they failed me. They are real tasks that I am trying to achieve, not me trying to set up the AI to fail. I am writing them up as I would a factual incident report which means they may be a bit dry and boring. There will be some of my opinion in there, but they are not intended to be entertaining or succinct.

Like so much of my blogging I write these more for my benefit than for you. Spending time reflecting on how these AI chats played out helps me be more objective about AI; it helps me decide what I think about this technology. I’m also hoping it will uncover ways to make the technology better, because if AI really is to be our future then it has to work for everyone—including the two-thirds of Australians who say AI creates more problems than it solves.

The series starts with a failed chat about Vanguard with Xero’s JAX AI chatbot.