In this guide
Start with the main guide, then come back
Our Microsoft 365 Copilot guide explains what Copilot does, what it costs and which licence you need. This page is the practical check that decides whether you are ready to buy. Five areas, each with a yes-or-no test.
1. Where does your data live?
Test: are your business files in SharePoint and OneDrive, and is email in Exchange Online?
Copilot reads Microsoft 365 and nothing else. Files on an office server, a NAS or personal Dropbox and Google Drive accounts are invisible to it, and it will answer confidently from what it can see, which is then incomplete. If the answer is "mostly", list what is elsewhere and decide whether to move it first. Our where should files live guide has the structure.
Also: is the data findable? Sensible site structure and file names matter, because Copilot references files by name and searches by content. "Final v3 (2).docx" is a Copilot problem.
2. Who can see what?
Test: have you run the sharing reports and fixed what they found?
Copilot respects permissions, which means it surfaces everything a person already has permission to see, including the HR folder shared with "Everyone" in 2019. Before licensing:
- Run the data access governance reports (SharePoint Advanced Management, available once a Copilot licence exists, so assign one to an admin first).
- Remove "Everyone" and "Everyone except external users" from sites holding HR, finance or client data.
- Set the default sharing link to specific people.
- Apply restricted content discovery to any site you are not ready to open up.
- Label confidential documents with sensitivity labels.
If none of this has been done, you are not ready, whatever the licence budget says.
Not sure which of these applies to your business? Ask an engineer.
Book a Discovery Call3. Who would actually use it, for what?
Test: can you name five to ten people and the task each would use it for weekly?
Copilot earns its keep for people who spend their day in email, documents and meetings: managers, sales, finance, bid writers, account managers. It is wasted on people who live in a line-of-business system. Write the list with the task beside each name ("summarise supplier threads", "first-draft proposals from our scope documents", "meeting recaps for the ops call"). If you cannot fill the list, start with Copilot Chat, which is free, and revisit.
4. Are people prepared?
Test: is there a training plan, a written rule set, and a champion?
Training by role, the slash-to-reference-files habit, checking output, and the rules for what may be pasted into which Copilot. A prompt library somewhere shared. Someone who will keep it alive after the first month. The main guide's training and rollout section sets out what good looks like; without it, licences go unused.
5. Can you measure a pilot?
Test: have you agreed the measures before the pilot starts?
Five to ten people, three to four weeks, and measures agreed in advance: self-reported hours saved per week, active use from the admin centre reports, time from meeting to follow-up, and who asks to keep the licence. Compare against a break-even; in the main guide's worked example it is about 17 minutes saved per licensed user per week. Then license the people who use it, and reassign the licences that gather dust.
How Black Sheep Support runs the readiness review
Our Copilot readiness review works through the five tests on your tenant: where data lives, the sharing reports and fixes, the use-case list with your managers, the training plan, and the pilot design with measures. You leave with a written answer to "are we ready?", the list of what to fix, and a pilot you can start. [TO CONFIRM: fixed fee and whether licence supply is included.]
Want a second opinion before you buy licences?
We will look at your tenant, tell you who would actually benefit, and what needs fixing first. An engineer, not a salesperson.
Frequently asked questions
What do we need before buying Copilot licences?
Files in SharePoint and OneDrive, email in Exchange Online, an oversharing check done and fixed, MFA everywhere, current Microsoft 365 apps, a named pilot group with use cases, and a training plan. The main Copilot guide has the licence prerequisites.
Can Copilot leak data?
It shows people only what they already have permission to see, which is often more than intended. The readiness work is finding and fixing overshared sites before Copilot makes them easy to find.
How long does readiness take?
One to three weeks for a business whose data is already in Microsoft 365; longer if a server or personal drives have to be migrated first.
Should we start with Copilot Chat?
Yes. It is included with your Microsoft 365 plan, it is safe under a work account, and it builds the prompting habit before you pay for the full product.
How many people should be in the pilot?
Five to ten who write and read the most, for three to four weeks, with measures agreed before it starts.
Book a Copilot readiness review
Find out whether you are ready before you spend on licences: what is where, who can see it, who would benefit, and how to run a pilot you can measure.
- The five tests applied to your own tenant.
- The oversharing findings and fixes.
- A use-case list and pilot group agreed with your managers.
- A pilot design with measures and a decision point.
Sources
Prices and product facts on this page were checked against the following Microsoft pages on the dates shown.
- 1.Microsoft Learn: Data, privacy and security for Microsoft Copilot (permissions) · accessed 10 September 2026
- 2.Microsoft Learn: SharePoint Advanced Management overview (data access governance, restricted content discovery) · accessed 10 September 2026
What has changed on this page
- 10 September 2026Page published as the readiness companion to the main Copilot guide.
