AI has been phenomenal. But if you use it for real work, you will know this routine.
Find the file. Drag it into the chat. Ask your question. Get an answer. Copy the answer out, or download the new file, rename it, and put it back where it belongs. Then do the same again with the next file, and the one after that.
At first it feels like magic, so you do not notice. After a few weeks you realise the AI is fast and you are slow. The bottleneck is not the thinking any more. It is you, dragging files in and out of a browser.
There are ways around it. Here are three, each a step further than the last.
1. Connectors: let the AI reach your email, drives and documents
The first step is the easiest. Both Claude and ChatGPT can connect to the places your work already lives: your email, your calendar, Google Drive or OneDrive, your documents. These are usually called connectors, and you switch them on in the settings.
Once they are on, you stop uploading and start asking. “Find the latest version of the supplier contract and summarise the payment terms.” “What did Sarah say about the launch date in her emails last week?” “Pull the figures from the March report into a table.” The AI goes and gets the file itself.
A word on privacy, because it is the first question most people ask. You choose which connectors to turn on, and you can turn them off again. Start with one, for example your calendar or a single shared drive, and see how it feels before you connect everything.
2. Claude Cowork and ChatGPT Work: bring in the files on your computer
Connectors cover what lives online. But plenty of work lives on your own computer: the folder of receipts, the drafts, the spreadsheets that never made it to the cloud.
That is where Claude Cowork and ChatGPT Work come in. They run as apps on your computer, and you give them access to a folder you choose. Now the AI can open what is in that folder, read it, and save its work straight back into it. No uploading, no downloading, no renaming.
This is the point where it starts to feel less like chatting with a clever assistant and more like working alongside one. “Go through the invoices in this folder and put them in a spreadsheet.” “Tidy these meeting notes and save each one as its own document.” You come back and the files are simply there.
3. Claude Code and Codex: go all the way
The third step sounds technical, and it is aimed at people building software, but do not let the name put you off.
Claude Code and OpenAI’s Codex work directly in the folders on your computer, like the tools above, and go further. They can run programs, build things, fix things, test them and try again, working through a job of many steps with you guiding rather than doing. It is how I rebuilt a website in a couple of days, and plenty of people with no interest in code now use Claude Code to organise files, analyse data and manage whole projects.
You do not need to start here. But it is worth knowing it exists, because it shows where all of this is heading: the AI working where your work lives, not in a separate tab you keep feeding.
Once you change, you will never go back
The first time you ask a question and the AI simply finds the file, it feels like a small thing. By the end of the week, going back to dragging and dropping feels like posting a letter when you could have sent an email.
Pick the step that suits you. Most people should start with one connector this week. If you are already there, try Claude Cowork or ChatGPT Work on a single folder. And if you want a hand working out which step fits the way you work, send me what you have.