Connect Your AI to Your Business Tools · Lesson 2 of 8

Lesson 2: Before you connect anything

20 minutes. Decide the rules first. It's much easier than undoing them later.

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A connector is like giving a new employee a key. Before you hand over a key, you decide which doors it opens. This lesson is that conversation, held with yourself (and your IT partner, if you have one) before anything is plugged in.

You'll leave with three things settled: your permission list, your plan, and who flips the admin switch.

Part 1: The permission list

Every connector has some mix of three kinds of power. Sort every tool from your Lesson 1 inventory into these.

1. What it can SEE (read). Search your inbox. Read a file. List open invoices. Look up a customer. Reading is where almost all the value starts, and it's the lowest risk.

2. What it can CHANGE (write). Draft an email. Create a calendar event. Add a note to a customer record. Create a draft invoice. Useful, and each one needs a "yes, I checked it" from a person, at least at first.

3. What it must NEVER do on its own. Send money. Issue a refund. Delete records. Send an email to a customer. Change who has access to a file. Change payroll. These either stay off entirely, or always require a person to approve each one, every time.

A good rule of thumb: if a mistake would cost money, embarrass you in front of a customer, or be hard to undo, it goes in column 3.

Two facts that make this easier:

  • The AI uses your login. It can only see and do what the account that connected it can see and do. If you connect QuickBooks with an owner account, the AI has owner reach. If you connect it with a limited user account, it doesn't. Connecting with the most limited account that still gets the job done is the single best safety move you have.
  • All three products can ask before acting. Claude shows an approval prompt ("Allow once" or "Always allow") when a tool wants to act. ChatGPT has app permission settings; under "Allow read actions" it reads without asking but asks before making changes. Copilot connectors ask before they create, update or delete. The exact defaults vary by plan and by tool, so check them. Lesson 6 shows how to keep it that way.
Part 2: Which plan you need

Here is what the vendors' own help pages said on October 7, 2026. Plans and prices change often, so check your account before you buy anything.

Claude (claude.ai)

  • Directory connectors (the built-in list): Claude makes them available on all plans, including Free. Some vendors set their own rule, though. HubSpot's help page, for example, says its Claude connector needs a paid Claude plan. Check the vendor's page for the tool you want.
  • Gmail, Google Calendar, Google Drive: available to all users.
  • Microsoft 365 (Outlook, OneDrive, SharePoint, Teams): available on all plans, but only with a work Microsoft 365 account tied to a business plan. Personal @outlook.com or @hotmail.com accounts can't connect. A Microsoft Global Administrator has to give a one-time approval for your organization.
  • Custom connectors (pasting in a web address a vendor gives you): all plans, with Free limited to one.
  • Team and Enterprise plans: an Owner has to add a connector for the organization before staff can connect their own accounts.

ChatGPT (chatgpt.com)

  • Apps are available to all logged-in users, but some apps and features are limited to paid plans (Plus, Pro, Business, Enterprise, Edu). Some apps may not be available in certain regions, including the European Economic Area, the UK and Switzerland.
  • Business plan: apps are on by default, and the workspace admin controls them.
  • Enterprise and Edu: apps are off by default until an admin turns them on.
  • Custom apps (what OpenAI calls developer mode): on Business plans, only admins and owners can enable it. You won't need it for this course.

Microsoft 365 Copilot

Microsoft renamed its tiers in 2026, so older guides use different names.

  • Microsoft Copilot Chat (the free tier, formerly Microsoft 365 Copilot Chat) comes at no extra cost with eligible Microsoft 365 business plans. It's grounded on the web. It can't search your mailbox, files and calendar by itself, though it can work with an email or Teams chat you have open, or a file you upload.
  • The paid Microsoft 365 Copilot license (sold to businesses of up to 300 users as Copilot Business) reaches your email, files, meetings, calendar and Teams automatically, through your own permissions.
  • Copilot connectors bring in other tools, such as Gmail, HubSpot, Xero, Square, Asana or Canva. Your Microsoft 365 admin turns each one on, and then each person signs in with their own account. Some write actions (creating or updating records) were starting to roll out in early October 2026, each with an approval prompt.
  • Agents come from the Agent Store inside Copilot. Your admin decides which ones staff may install.
  • Copilot Studio, where an admin or IT partner can plug an MCP server into a custom agent, is a builder's tool. You won't need it for this course.

If you're not sure which plan you're on: in Claude and ChatGPT, open your account or settings page and look for the plan name. In Microsoft 365, ask whoever pays the Microsoft bill, or check the Microsoft 365 admin center under billing.

Part 3: Who flips the admin switch

On a personal or single-user plan, you are the admin. Skip ahead.

On a team plan, someone has to turn connectors on for everyone first:

  • Claude Team or Enterprise: the Owner or Primary Owner, under Organization settings, then Connectors. Staff who want one that isn't added yet will see a "Request" button.
  • ChatGPT Business or Enterprise: the workspace owner or admin, under Workspace settings, then Apps. They can allow all actions, read actions only, or a custom set.
  • Microsoft 365 Copilot: your Microsoft 365 admin (or IT partner) enables Copilot connectors in the Microsoft 365 admin center and controls which agents staff can install.
  • Claude with Microsoft 365 data: Claude's Microsoft 365 connector needs a one-time approval from someone with the Global Administrator role in Microsoft Entra (Microsoft's sign-in system).

If you have an IT partner, send them a short note now. Something like:

> We want to connect [Claude / ChatGPT / Copilot] to [Outlook and SharePoint / Gmail and Drive / QuickBooks]. Read-only to start. Can you tell us what needs admin approval, and turn on only what's on the attached worksheet?

Attach the worksheet you're about to fill in.

Exercise: fill in the Connector Permission Worksheet (15 minutes)

Open the Connector Permission Worksheet template for this course.

  • Copy your three circled tools from Lesson 1 into the worksheet, plus your email and calendar.
  • For each one, fill in the three columns: Can see, Can change (with approval), Never on its own.
  • Write which account will connect it. Prefer a limited user over an owner account.
  • Write which plan you're on and whether an admin has to approve it.
  • Mark each row's starting mode: Read-only or Read and draft. Nothing starts as "send, pay or delete."

Check it worked

Read your worksheet out loud. For every tool, you can answer in one sentence: "The AI can see _, it may draft _ for me to check, and it may never _." If any row has an empty "Never" column, fill it in. Every tool has something it should never do alone.

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Next: your first real connection. Email, calendar and files.

→ Lesson 3: Connect your email, calendar and files

Previous: Lesson 1: What connectors are and why they matter now · Next: Lesson 3: Connect your email, calendar and files