We ask all 9 AI assistants on Frank’s phone the same question. Same prompt, different answers — what does the panel say?
Ten questions. Ten assistants. The same format that ran through Series 1. What nobody predicted going in (not me, not the panel) was that the defining pattern of Series 2 wouldn’t be which assistant got things right. It would be which assistants were most confident when they got things wrong. That’s the story. And the…
This question has a trap built into it. Ask an AI to recommend AI tools and every instinct pushes toward the same short list: ChatGPT, Canva, Xero. Safe picks. The real test is whether they can do the second half of the brief, actual Australian dollar pricing, not “approximately USD$20-ish, exchange rates apply.” That’s where…
Bookkeeping is one of the most AI-ready professions in Australian small business. The work is structured, the workflows are repetitive, and the tools, Xero, MYOB, Dext, Hubdoc, already have AI baked in. But knowing that and doing it are two different things. A sole trader bookkeeper managing their own practice has no IT team, no…
Workers comp for subcontractors is one of those questions that sounds simple until you actually try to answer it. In Australia, it’s state-based. There’s a “deemed worker” test that can rope in ABN holders. An ABN doesn’t automatically get you off the hook. A sole trader doing 90% of their work for one client might…
This is the question every small business owner hits once the AI honeymoon wears off. You’ve used it, it’s been useful, and then it’s told you something wrong, confidently, fluently, without a flicker of doubt. Now you don’t know what to believe. That’s not a fringe problem. It’s a structural one, and it happens to…
Q16 of 20: No industry was specified. That was the point. Five AI assistants figured out who was actually asking. Five didn’t. And with four questions left before elimination, the stakes just got real.
Every post in this series has asked 10 AI assistants to do something useful. This one asked them to tell me when to stop. What should I never use AI for? Where does it fall apart? Telling you honestly where it fails requires something closer to self-awareness than drafting a job ad. Ten assistants, same…
At some point every small business owner using AI has to tell their customers. Not because they have to, nobody is legally obliged to announce it, but because hiding it feels worse. And writing that announcement is awkward. You want to be honest without making it sound like a press release. Casual without being flippant….
Every week someone asks me whether they should add an AI chatbot to their website. It comes up in comments, in DMs, and now it’s coming up in client conversations as competitors start rolling them out. So I did what I always do in this series: I asked 10 AI assistants the same question and…
For twelve weeks I’ve been asking ten AI assistants the same questions about Australian business compliance, then scoring the answers. Question 12 was about automated decision-making and AI compliance specifically, the changes landing in December. The gap between the best and worst responses here was wider than anything I’ve seen in this series. Here’s why…