Copilot readiness checklist: 10 things to check before you buy

Most businesses that are disappointed by Copilot weren’t let down by Copilot. It simply couldn’t see their files, or nobody knew what to ask it. This checklist covers what to sort out before you pay for a seat or start the free trial. In a small business it takes an afternoon, and you don’t need to be technical for most of it.

The checklist

1. Everyone who will use Copilot has a Microsoft 365 business plan and signs in with a work account.
2. Work files live in OneDrive, SharePoint or Teams, not on laptops, an office server, Dropbox or Google Drive.
3. Shared files are in a few clearly named places, and old copies are archived or deleted.
4. Sensitive folders (payroll, HR, contracts) are shared only with the people who need them.
5. Nothing private is shared with “anyone with the link” or the whole company by accident.
6. Teams meetings that matter are recorded or transcribed, so Copilot has something to recap.
7. Everyone is on current versions of Outlook, Teams and the Office apps.
8. You’ve picked the one to three people who get a paid seat first.
9. Each of them has written down three tasks that take real time today.
10. There’s a date on the calendar to review whether it paid off.

Here’s what each one means and how to check it.

Your Microsoft 365 setup

A business plan and work accounts. The paid seat, Copilot Business, is an add-on to Microsoft 365 Business Basic, Standard or Premium. Each of those plans also includes the free Copilot Chat. If some people still use personal Outlook.com or Gmail addresses for work, Copilot can’t help them with that email.

Current apps. Copilot shows up inside Outlook, Teams, Word and Excel, but only in versions Microsoft still updates. If someone is on an Office version bought once years ago, they won’t see it there.

Your files

Copilot only sees Microsoft 365. That means your email in Outlook, chats and meetings in Teams, and files in OneDrive and SharePoint (Teams files are stored in SharePoint). Anything else is invisible to it. Moving shared work files into SharePoint or a Team is the single biggest thing you can do to make Copilot useful.

Tidy beats complete. If there are five versions of your price list, Copilot may quote the old one. Keep one current copy of the documents people rely on, such as price lists, procedures, templates and the employee handbook, and archive or delete the rest.

Check that Copilot can read them. Scanned PDFs and photos of paper often hold no text Copilot can use. Our free document check on sierrix.ai shows what Copilot can actually read from a PDF, Word or Excel file.

Who can see what

Copilot never shows a person anything they couldn’t already open themselves. But it is very good at finding things, so a file that was shared too widely years ago and forgotten becomes easy to stumble on.

• Open the folders that hold payroll, HR, contracts and customer records and check who they are shared with.
• Look for “anyone with the link” or “people in your organization” links on anything private, and remove them.
• If you have an IT person or provider, ask them to run a sharing report in the SharePoint admin center.

Meetings and email

Meeting recaps need a transcript. Copilot sums up a Teams meeting from what was said, so turn on transcription (or recording) for the meetings you want recaps of. Let attendees know, and check the rules for recording calls where you work.

Email is ready as it is. Copilot works with each person’s own inbox, so there’s nothing to move.

People and tasks

Start small. Give paid seats to the one to three people with the most email, meetings and documents. Everyone else can use the free Copilot Chat in the meantime. Our guideIs Microsoft Copilot worth it? shows how to work out who that is.

Write down the tasks. People who start with “let’s see what it can do” tend to stop using it. People who start with “write my weekly update from these three emails” keep going. Three real tasks each is enough. If you need ideas, How to find the tasks AI can take off your plate walks through it.

Set a review date. The free one-month trial turns into a paid one-year plan unless you cancel, so put the review a few days before it ends. For prices and contract terms, seeWhat does Microsoft Copilot cost?

Common questions

Do I need to prepare before buying Copilot?

A little. Copilot can only use what is in Microsoft 365 and only what each person already has access to. Moving work files into OneDrive or SharePoint and checking who can see sensitive folders takes a few hours in a small business and makes Copilot far more useful from day one.

Can Copilot see files people should not see?

Copilot only shows a person what they already have permission to open. The risk is files that were shared too widely in the past, for example with a link anyone in the company can use. Copilot makes those easier to find, so check sharing on sensitive folders such as payroll and HR before you start.

Does Copilot work with files on my computer or in Dropbox?

Not on its own. Copilot works from Microsoft 365: Outlook, Teams, OneDrive and SharePoint. Files on a laptop, a server in the office, Dropbox or Google Drive are invisible to it unless you upload them into a chat.