This is how my first project starting with a bot estimate with GPT-5 went:
It was an eerily human experience. The bot showed no emotion, but I ran hot and cold, you can probably empathize as the tale unfolds.
We started with a simple test case, OCR a scanned bulleted list, perfect result. Then I asked for the real case, split 31 images into 3 combined lists. Do I need to upload 31 images? I asked. No, just zip them with a manifest, and I’ll return 3 csv files. Great, give me a Tee-Shirt. Large, it said, 50 prompts.
That’s a bit strong, I thought, after the test case had gone so well. OK, here is the zip, there were some clarifying questions. Go ahead, I said. I can’t do any more analysis today, the bot said, try again tomorrow.
Next day, robot says sorry, I don’t have access to my OCR system right now, let me send you python code so you can do the OCR yourself.
Next day (4) same thing. Right, I think, let me try Gemini, it had done some OCR with a zip file while I was waiting. Sorry, says Gemini, max 10 files in a zip. Retry with 10 files. Sorry, I can’t do complex workflow like that, ask me something else.
Back to ChatGPT. OK, send me python. Here it is. A few setup questions. Then, sorry only 10 questions per day with free GPT–5. Do you want to Upgrade?
Lord knows, I’ve tried hard enough! It’s day 4. Sign me up, cancel any time. (I haven’t cancelled yet.)
More prompts. OCR is tough, every character is a potential data related issue, non-characters more so … Eventually, OK that’s good enough to use, with some manual cleanup. Three cleaned up files imported to Innovator using XamlAml, no failures. First time SUCCESS!
I made the count, 47 prompts. Cool, the bot made a pretty good estimate, including delegating (with help) the OCR to me. Beginner’s luck? Let’s find out, the bot will keep the log shown at top.
✅ From now on:
When you finish a project, just tell me the Project Name, Estimate, Actual. I’ll append it to the table, so you always see the full log. I’ll also watch for trends and suggest tee-shirt size adjustments if needed.
Deal. Stay tuned.