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Today's issue comes with a downloadable practice pack, and I want to know if that's the right shape before I make more of these.
One Click before we start:
If I made more practical guides like this one, how would you actually want them?
Pick the one you'd actually use.
I had a folder full of messy files and needed one clean document from them. So I did what I had always done: uploaded the files into a chat, copied the answer into Word, fixed the formatting, and moved the document back into the real folder. Sometimes the result was useful. Other times it came back messy enough to make me wonder whether I was using AI the wrong way.
Then ChatGPT introduced Work, while Claude has Cowork. Both can connect directly to a folder on your computer. I still had one basic question: when should I use Work or Cowork instead of regular Chat? That is what today’s issue answers.
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Here's the rule I use:
Chat for a conversation. Work or Cowork for a handoff.
Stay in Chat when you want to think with the AI: drafting, or arguing an idea through. Open Work or Cowork when you want to hand over a bounded job and get a checked file back.
The tools overlap. Chat can read files, and Work and Cowork can hold a conversation. The rule is about how you want to work, and it tells you where to start.
Why the folder matters: with Chat you find the files, upload them, download the result, then send it on. With a connected folder the files are already where they live. The result lands next to them, and you can edit it and send it from there.
Connecting a folder means creating a project, and a new project for every task is a habit you'll drop by week 2. So make the folder the piece of work, with a subfolder per job inside it, connected once. Each job is a new chat, and the first line of the prompt names the subfolder it's allowed to touch.
One safety rule: work on a copy. The permission screen says the app may edit, delete, or share files in that folder. Duplicate the folder first, if you are using it for the first time.
🔍 The run I checked before writing this
I built a practice folder to test this: a made-up bakery planning a workshop, 3 files of planning notes and signups.
One prompt to ChatGPT Work: read the 01-FIRST-RUN folder only, build a one-page Workshop plan.docx, and if the files disagree, show me the disagreement.
Then I sat with the sources and checked it. 18 signups, 9 of them online. All 9 online signups asked about a recording. 0 of the 9 in-person ones did. The plan caught that split and put the count next to a question the organizers never answered: whether the recording is included, sold separately, or not offered at all.
It also connected 2 facts sitting far apart in the notes. One call proposed Saturday 12 September. A later call said one organizer is away the first 3 weeks of September. The plan kept both dates and marked the final one undecided.
Then the part I actually wanted to test. One more prompt turns the method, corrections included, into a plain-text file called WORKFLOW-INSTRUCTIONS.txt. If you already run projects in ChatGPT or Claude, this file is the move worth stealing: the method lives in plain text at the top of the folder, so any app can read it.
The second run proved it. New subfolder, 4 files this time, including a budget PDF the first job never saw. Different app too: Claude Cowork instead of ChatGPT Work. The prompt was 3 lines, because the method was already in the file.
It caught the trap I'd planted. 22 signups against a confirmed capacity of 20. A cap raised from 12 to 20 after a bigger room opened up. And a $55 price that was agreed before the room changed, then questioned, then left unresolved. The plan treated that price as an open question, on files the first agent had never seen.
⚡ The part that went wrong
The first plan got saved at the top level of the folder instead of inside 01-FIRST-RUN. The agent said it created the file, and that was true, just not the part I cared about. So open the folder and look, every time. The fix is one sentence: "Workshop plan.docx belongs in 01-FIRST-RUN, move it there." I added that as a rule to the instructions file, and the second run filed its plan correctly.
📨 Try it on the same files
The practice pack has the bakery folder, a START-HERE page, and every prompt ready to paste. About 10 minutes to a finished file. The reusable half takes roughly 10 more, and if you only came for one finished file, you have it, and you can stop there.
If AI never became a habit you actually use, this is a decent restart. The files are fake and the prompts are already written, so the practice is checking the result.
You'll need a computer. Both apps work with folders on your own machine, and that part doesn't happen on a phone.
On your phone right now? Reply FOLDER and I'll send the pack so it's waiting when you're back at a desk.
Dan Rice · AI Signal Read once. Use AI better all week.