Raidiness

Why I built Raidiness

"Are we ready for Copilot?" I get that question a lot. The honest answer is usually: it depends. What do you want to use it for, what can your users already reach, and what does your tenant actually look like?

I built Raidiness to answer that last part faster. It's a PowerShell tool that reads your Microsoft 365 configuration, checks it against AI readiness criteria on your own machine, and gives you a report with findings you can work with.

Think of it as a pre-flight checklist. It won't fly the plane for you, but it tells you what to look at before you take off.

What Raidiness checks

Microsoft Graph is the core. Depending on what you plan to roll out, you can add other workloads, plus a short intake with the questions your tenant can't answer.

Source	What it looks at
Microsoft Graph	Users, licenses, groups, sites, usage, identity and governance settings, as far as your access allows.
Exchange Online and Purview	Mailbox counts, audit settings, sensitivity labels, DLP policies, retention and label activity.
SharePoint Online	Tenant settings, site inventory and optional permission sampling.
Microsoft Teams	Meeting policies. It doesn't show which policy applies to every individual user.
Power Platform	Environments and connector DLP policies for Copilot Studio governance. Not a complete list of all agents.
Intake	Which AI features you plan to use, the decisions behind them and context the tenant can't give you.

What you get back depends on your permissions, roles, licenses and the modules you pick. If a check says Not measured, Raidiness didn't have enough data to judge it. That's not a pass and not a fail. It's something to look into.

For how I use all of this in practice, read my AI Readiness Check for Microsoft 365.

What the report gives you

In version 0.5, Raidiness collects the sources you selected, checks them locally and builds a report. The HTML viewer shows the findings, the measurements and the gaps in one place. You also get Markdown and a printable version to review with others, and JSON with all the details.

Do note that Raidiness doesn't make the decision for you. It won't approve a rollout, write a business case or decide which risks are acceptable. A successful run only means the command finished. You still have to check what it could measure, and whether that covers the users and scenarios you have in mind.

The published release on PowerShell Gallery can differ from 0.5. My installation guide explains which command to use for your version.

Read-only and local

Raidiness only reads from the Microsoft services you select and writes the results to a folder you choose. It doesn't change tenant settings, doesn't give itself extra permissions, doesn't send anything to me and doesn't call an AI model.

It's good to know that the reports can contain names, email addresses, tenant IDs, site URLs and configuration details. Store them somewhere approved: your Documents folder might be synced to OneDrive or picked up by backup software.

There's also an optional LLM export. It creates local files you can review and use with your own model. Nothing gets uploaded, but your organization's data rules still apply if you decide to share them.

Who it's for

Raidiness is for Microsoft 365 admins, engineers and consultants who want a repeatable starting point for a Copilot readiness assessment. Run it before a pilot, before you add a new AI feature, or after changes to see what moved.

It's free on PowerShell Gallery under the MIT license. You still need the right Microsoft licenses and permissions for the workloads you check.

Questions about the tool or your own tenant? Get in touch.