ChatGPT for Your Team · Lesson 5 of 7

Files, connected apps and plugins

20 minutes. For everyone. Bring in the documents you need. Connect only what you'll use. Keep a person on the approve button.

---

ChatGPT gets much more useful when it can see your real documents. A price sheet. A long contract. Last month's job list. It can also connect to the tools you already use, like Google Drive, SharePoint, Outlook or Slack, and find things there.

Both come with a simple trade: the more ChatGPT can see and do, the more care it takes. This lesson covers files first, then connected apps, then plugins.

Part 1: Files

What you can upload

OpenAI's help page lists these types:

  • Documents and text: DOCX, PDF, TXT
  • Spreadsheets: XLSX, XLS, CSV, TSV
  • Presentations: PPTX
  • Images
  • Audio (on paid plans, including Business): common formats such as MP3, M4A and WAV

One catch: you can't upload a Google Docs file directly. Export it as PDF or DOCX first.

How big, how many

From OpenAI's limits:

  • Documents and presentations: up to 512 MB per file
  • Spreadsheets and CSV files: about 50 MB, depending on the rows
  • Images: up to 20 MB each
  • Up to 80 files every 3 hours, which OpenAI may lower at busy times
  • Shared storage is capped at 25 GB per user and 100 GB per organization

For a small office, you'll rarely hit any of these. The more likely problem is a messy file. A scanned PDF with no real text, or a spreadsheet with merged cells and notes in the margins, gives worse answers. Clean, text-based files work best.

Try it (5 minutes)

Pick one real document. At Comfort Zone Heating & Cooling, our fictional HVAC company, Dana uploaded the maintenance plan terms and asked:

> Read this maintenance plan document. List every promise we make to the customer, with the section it's in. Plain text, one line each.

Then she checked three of the promises against the document herself. Do the same: ask a question you know the answer to, and check the answer against the file. That's how you learn how far to trust it.

Where files end up

This matters for cleanup. OpenAI's pages say:

  • A file you upload in a chat can be saved to your Library, separate from the chat.
  • Deleting a chat doesn't delete a file saved in Library. Delete it from Library too if you want it gone. You can check your Library storage in Settings > Storage.
  • Files in a project stay until the file or project is deleted.

Rule for the team: before you upload, ask, "Would I be fine with this file sitting in the company workspace for months?" If not, remove the sensitive parts first, or don't upload it.

Part 2: Connected apps

An app connects ChatGPT to another service so it can search, read and sometimes act there. OpenAI lists apps for Google Drive, SharePoint, Microsoft Teams, Outlook email and calendar, Slack, Box, Notion and others.

Connect one app (5 minutes)

OpenAI's steps:

  • Open Settings > Plugins and select the app, or the plugin that includes it.
  • Select Install plugin if it's shown.
  • If asked, select Connect and sign in to the account that has the information you need.
  • Review what it asks for before you approve.

Then use it in a chat by typing @ and the app's name, or selecting + and choosing it. For example:

> @Google Drive find our 2026 price sheet and list the prices for furnace tune-ups.

If an app shows Disabled by admin, your owner turned it off in Lesson 2. Ask them.

What an app can see

Three facts from OpenAI's pages to know before you connect anything:

  • An app sees only what your account can see. It uses the access of the account you sign in with. It can't reach files you couldn't open yourself.
  • An app may see some of your ChatGPT context. OpenAI says an app you enable may use relevant parts of your conversation, and your memories if Memory is on, to do its job. What the app does with that is governed by the app's own terms and privacy policy.
  • In Business, OpenAI doesn't train on information from connected apps by default.

Set when ChatGPT asks first (5 minutes)

This is the setting that keeps a person in charge. OpenAI's app permission options include:

  • Always ask
  • Allow read actions
  • Allow low-risk actions
  • Allow all actions (for an eligible app or account)

OpenAI warns that Allow all actions "carries elevated risk," because actions may run without another confirmation.

The calm choice for a small business: Always ask, or Allow read actions for apps that only need to find things. Never use Allow all actions for anything that can send email, change a calendar, post a message, or touch money.

And when ChatGPT does ask, read the request before you approve it. Who is it sending to? What is it changing? An approval click is the same as doing it yourself.

To remove an app's access completely, disconnect it in Settings > Plugins. Changing a permission only changes when ChatGPT asks first.

Part 3: Plugins

OpenAI now groups apps and reusable instructions into plugins. A plugin can include one or more apps, plus "skills" that give ChatGPT instructions for a task. You'll find them under Plugins in the sidebar. They're also where custom GPTs are headed (Lesson 4).

Two things to know:

  • Installing a plugin doesn't skip any permission. You still sign in to each app, and workspace controls still apply.
  • A badge isn't a review. OpenAI says its "OpenAI Verified" badge doesn't replace your own privacy and security review. Before the team installs a plugin that connects to company systems, the owner should approve it.
Do this now
  • Upload one real document and ask a question you can check.
  • Connect one app the team actually needs, with Always ask or Allow read actions.
  • Use it for one real task, and approve or decline any request yourself.
  • Add the app rules to your Team ChatGPT Card.

Check it worked

  • You checked at least one answer from an uploaded file against the file itself.
  • Every app you connected is set to Always ask or read only.
  • Nobody on the team uses Allow all actions.
  • You know where your saved files live, and that deleting a chat doesn't delete them.
  • The owner has approved every plugin that connects to company systems.

---

Next: what all this costs, and how to keep it predictable.

→ Lesson 6: Costs, seats and what's included

Previous: Projects, custom GPTs and sharing · Next: Costs, seats and what's included