Free AI readiness assessment
Know what AI would find in your files before anyone turns it on
A free, one-week review of your Microsoft 365. We show what Copilot or any AI assistant could find for each department on day one, what to fix first, and what it would cost. Nothing in your systems changes.
Free · about one week · view-only · no obligation
View-only access your IT administrator approves and removes. Nothing in your systems changes.
We reply within one business day.
Microsoft Co-Sell Ready · FastTrack Ready Partner
Delivered for Orange County Transportation Authority, City of Boulder, Town of Bluffton, San Diego Housing Commission, South Tahoe Public Utility District, Foothill Transit and more.
Short answer
The AI readiness assessment is a free, one-week review of an organization’s Microsoft 365. It shows what Microsoft 365 Copilot or any AI assistant could find for staff today, which files and information are open to more people than they should be, and what to fix before AI goes live. You receive a written report and a fixed-price plan to keep, with no obligation.
Starting points
Who it is for
The cost of waiting
AI does not create new risks in your files. It shows the ones already there.
An AI assistant sees only what its user can already open.
Files shared too widely years ago were always reachable, just hard to find. AI makes them easy to find, simply by asking.
What we check
What the assessment covers
Files open to too many people
Folders, sites and links that everyone in the organization can open, and where they are concentrated.
Who has access to what
Sites and folders with far more members than the team that owns them, and access nobody remembers granting.
Confidential information left unprotected
Where personal, financial and legal information is stored, and whether it is marked and protected.
Accounts with too much access
Administrator accounts, former staff and outside guests who still have access.
What AI would find
What a typical employee in each department could find on day one, tested with the questions people really ask.
Records of who did what
Whether your systems record activity well enough to answer an audit or a public records request.
What you receive
A report you can act on the same week
Every finding is ranked by how sensitive the exposed information is, with the fix, the effort and who on your team can do it.
- Access map: every site, folder and link open to more people than it should be.
- What AI would find: real questions we asked as a typical employee in each department, and what came back.
- Fix list: what to change first, what your own team can do, and a fixed price for anything you want us to do.
- A straight answer: ready for AI now, or what has to happen first.
Why us
We run AI on Microsoft 365 every day
We do not only advise on AI readiness. Our own business runs on AI agents we built on Microsoft 365 and Azure: 29 projects, 20 of them in production. We know what an assistant can reach because we give agents access, review it and log it every day.
Your options
A checklist, a dashboard, or an assessment
There are cheaper-looking ways to check readiness. They answer a narrower question.
| Readiness checklist | Built-in admin reports | Our assessment | |
|---|---|---|---|
| Covers | Licenses and settings | Warning signs only | Files, access, confidential information, accounts and what AI would find |
| Tested with real questions | No | No | Yes, for each department |
| What you get | A checklist | Dashboards | A ranked list of fixes and a clear go or no-go |
| Cost | Usually paid | Included in licenses | Free |
View-only
We can look, but we cannot change anything
- Your IT administrator gives us view-only access, and sees the exact list of what we can read before saying yes.
- We cannot change, delete or move anything in your systems.
- No documents are copied out of your Microsoft 365, and no AI tool is given access to your data.
- Our access is removed at the end of the week.
For your IT team: read-only Microsoft Graph application permissions, consented by your administrator, with no write permissions.
Our promise: view-only from start to finish. If we ever need more, we ask in writing first.
The offer
One week, view-only, and a report you keep
You get a map of what is open to whom, a report of what AI would find, and a ranked list of fixes, plus a straight go or no-go on AI and what has to happen first.
Access map
Where files are open to too many people, ranked by how sensitive they are.
What AI would find
Examples from your own Microsoft 365 of what an employee in each department could find today.
Fix list and fixed price
What to fix and in what order, what your own team can do, and a fixed price for anything you want us to do.
- Free, with no obligation
- About one week
- View-only: nothing in your systems changes
- The report is yours to keep
Why free? Any responsible AI project starts here, and the report shows you what to fix whether or not you hire us.
How it runs
Day 030-minute call and the exact list of what we will read.
Days 1–2Your IT administrator approves view-only access.
Days 2–4We review your Microsoft 365 and test what AI would find, department by department.
Day 5Results meeting. You keep the report, and our access is removed.
View-only access approved by your administrator and removed at the end. No documents leave your Microsoft 365. NDA and data processing terms are signed before any access.
After the assessment
What fixing it typically costs
The assessment is free. If it finds work to do, here is what that usually looks like.
| Next step | Typical timeline | Typical investment |
|---|---|---|
| Fixes: access, protection of confidential information | 2–8 weeks | Fixed price, set in the assessment |
| First AI pilot | 6–8 weeks | Fixed price, set in your plan |
| Production deployment | 3–6 months | Fixed price, set in your plan |
What clients say
Agencies and businesses that trusted us with their Microsoft 365
Town of BlufftonProject team
When the Town of Bluffton decided to implement a Document Management System, we put our RFP out and Communication Square answered the call with great pricing and Customer Service. Through much work and input, Communication Square helped us develop our DMS in our SharePoint environment. They were extremely flexible as we changed our minds on what we wanted many times. Though we are still in the implementation phase, Communication Square has been very responsive and always willing to help us adjust and become more familiar with our new system.
Roy EseyanInformation Technology Manager, Foothill Transit
To ensure that regular bugs are fixed, security updates are accomplished, and problems are solved, we trusted Communication Square to carry out a hassle-free migration.
Bryan KuesterPresident, Kuester Management Group
We have been working with Communication Square since 2015. After using Skype for Business for so many years, we were trying to avoid change and not want to move to Teams, until their Support Team demoed to us their own Teams setup, and we suddenly got excited after seeing everything in action. Add onto it the Change Management Process they helped us adopt; it was smooth as in a lake.
Questions buyers ask
Before you decide
Can Copilot see files a user is not allowed to open?
No. Microsoft 365 Copilot only uses content the signed-in person already has permission to open. The real risk is the opposite: files shared with everyone years ago become easy to find just by asking. That oversharing is what the assessment finds and ranks.
Do we need sensitivity labels before we turn on Copilot?
Not to switch it on. Labels, together with Microsoft Purview data loss prevention, are how you keep Copilot away from your most confidential files. The report shows where labels matter and where fixing who has access is enough.
Which licenses do we need for Microsoft 365 Copilot?
Microsoft 365 Copilot is an add-on to an eligible plan, such as Microsoft 365 E3 or E5, Business Standard or Business Premium, or the government G3 and G5 plans. Copilot Chat is included for anyone signed in with a work account. The report shows which teams would benefit before you buy add-on licenses.
Our staff already use ChatGPT or other AI tools. Does the assessment cover that?
Yes. We list the AI apps and add-ins that users or administrators have connected to your Microsoft 365, what each one can read, and who approved it.
What access do you need?
View-only access approved by your IT administrator (technically, read-only Microsoft Graph application permissions). We can never change anything, and access is removed at the end.
We use Microsoft’s government cloud (GCC or GCC High). Does it still work?
Yes. We are an AOS-G partner and run the assessment in government clouds. AI features reach government clouds later than commercial ones, so the report states what is available in your cloud today.
Start by looking
You do not have to decide anything about AI to do this. You only have to find out what is already exposed.