Agent 365 readiness
Check ownership, identity, inventory, and the approval path before agents scale.
Check who owns each agentFREE CHECKS
Find the next control to fix.
Choose one short check. The PDF summarizes the questions and practical next steps. A separate conversation is available when you want help with the findings.
01 Source02 Boundary03 Human decision04 Evidence
AI security and agent governance check
Inspect data reach, action gates, monitoring, and recovery.
Review my AI security boundaryCopilot readiness
Test the content and identity controls that shape what Copilot can return.
See what Copilot could findCMMC readiness
Map the contract boundary and evidence ownership before an assessment.
Map my CMMC evidence gapsPrivate AI readiness
Choose the data and operating boundary before selecting a model or device.
Test my private AI boundaryCloud security check
Connect access, telemetry, and response ownership across the Microsoft estate.
Review my cloud response pathFREE TOOLS
Five pages that write the first draft for you.
Each one writes its result from a rules table, not a model, and cites the Microsoft control behind every line with the date it was checked. Each result keeps its own address, and nothing is stored unless you ask for the email. They share one register in your browser, and the register binds into one procurement pack.
Governed AI Blueprint
Nine answers about one workflow. Five controls marked tested, assumed or not yet, a readiness band and your first ninety days.
Open the Governed AI BlueprintAI Governance Simulator
Your tasks in your tools: which to hand to AI first, the hours back, the run with a person at the gate, and the two incidents that happen in practice.
Open the AI Governance SimulatorAI Use Policy Builder
Twelve answers write the one-page policy everyone signs, with the control behind each clause, as Word and PDF.
Open the AI Use Policy BuilderAgent Inventory Builder
Up to six agents, seven columns each: owner, reach, actions, approval, identity, stop path, last review. The three fixes first, with a CSV for your register.
Open the Agent Inventory BuilderVendor AI Due Diligence Questionnaire
Nine answers write the questions to send a vendor that uses AI, the deciding ones first, as Word and PDF.
Open the Vendor AI Due Diligence QuestionnaireTHE OFFER
What is a free check?
Four questions for the team that owns the decision, on one topic, with a PDF you can download directly and no email required.
Six checks exist today: Agent 365 readiness, AI security and agent governance, Copilot readiness, CMMC readiness, private AI readiness and cloud security. Each finds the next control to fix before a formal assessment, and each is ungated by design.
THE MICROSOFT INSIGHT
What can you learn about oversharing before any assessment?
A great deal. Oversharing means files reachable by more people than intended, and Microsoft Purview Data Security Posture Management for AI runs a weekly data risk assessment of the most used SharePoint sites without activation.
Microsoft Purview Data Security Posture Management for AI runs a weekly data risk assessment of the 100 most used SharePoint sites without activation and reports AI interactions that touch sensitive data. (Microsoft Learn, checked Oct 31, 2026)
Read that report and the free check before the call and the call starts at the finding. Skip both and the call starts at the slide.
THE METHOD
How does a four-question check lead to a decision?
Each question maps to a control, each control to a tested or assumed status, and the four together name the next control to fix.
- Answer the four questions with the people who own the decision.
- Download the PDF; it names the control behind each question.
- Mark each control tested or assumed in your own words.
- Bring the page to a scoping call, or fix the assumed control first.
THE GATING
Why is nothing gated behind an email address?
Because a check that asks for your email before it helps you is a lead form, and the firm would rather you fix the control.
You can ask for the PDF by email if you prefer. That creates an inquiry with Simplicity IT; marketing email is a separate choice with its own box.
Ungated, the check gets used by the person who needs it. Gated, it gets used by the person willing to be called.
THE NEXT RUNG
What comes after the check?
A read-only assessment scoped separately from any implementation, quoted after a scoping call, Microsoft-funded where you qualify.
The assessment produces the one-page Tested or Assumed record and the first permission rows (what each AI step may see, draft and do, and who approves). Nothing in your Microsoft 365 (your tenant) changes until you decide in writing.
AFTER TWO WEEKS
What will be working after two weeks?
- You have taken the check that matches your question and hold the PDF.
- Each of its four controls is marked tested or assumed in your words.
- You know which control to fix first and who owns it.
- You have booked, or decided not to book, a scoping call.
HONEST ABOUT LIMITS
What this does not do yet
It does not tell you what Copilot would return to a specific person. Microsoft 365 Copilot returns only content the signed-in user already has at least view permission to see, so anything shared too widely is findable from day one. (Microsoft Learn, checked Oct 31, 2026) That takes the read-only assessment inside your tenant, against your permissions.
It does not replace an assessment: four questions find the next control, they do not test it.
It does not create a lead unless you ask for the PDF by email and say so.
THE ONE THING TO REMEMBER
Four questions, one control to fix next, and no email required.
Said another way: find the assumption before the assessment finds it for you.
Said a third way: the check is for the person who owns the decision, not for the person willing to be called.
SHOW YOUR WORK
See the control path on a fictional bank.
What a pasted prompt can expose
A fictional bank tests the data boundary before access widens.
Coming
See every demonstrationDIRECT ANSWERS
Questions before you decide.
Is the PDF really free and ungated?
Yes. Download it directly from each check page. Asking for it by email is optional and creates an inquiry; marketing email is a separate box.
Which check should I take first?
The one that matches the decision in front of you. Copilot readiness before a rollout. Agent 365 readiness before agents scale. AI security before an audit. Private AI before hardware. CMMC before an assessment. Cloud security before a renewal.
What is the difference between a check and an assessment?
A check is four questions that find the next control to fix. An assessment is read-only work inside your tenant that tests the control and produces a written record.
Can Microsoft fund the assessment?
Microsoft-funded where you qualify. Eligibility is checked for your tenant before it appears in a proposal, and no funding figure is quoted in public.
How is the assessment priced?
Quoted after a scoping call, and scoped separately from any implementation.
NEXT STEP
Start with a boundary you can explain.
Choose a focused check, or speak with the team about the workflow you need to improve.