What a Microsoft 365 Assessment Covers, Plus a Self-Check to Run First

What a Microsoft 365 assessment reviews, from licensing and admin roles to sharing and Secure Score, plus a self-check an owner can run first.

Checklist · By NexJen IT Solutions · Reviewed October 2026 · 6 min read
Key takeaways
A Microsoft 365 assessment is a structured, read-only review of how your tenant is licensed, secured and organized, ending in written findings ranked by risk.
You can answer a useful first set of questions yourself, without admin access, and bring those answers to any assessment.
A general optimization assessment and a security posture assessment overlap but answer different questions, so pick the one that matches the decision in front of you.

A Microsoft 365 assessment is a structured review of how your company's Microsoft 365 environment (your tenant) is set up today: what you pay for, who can do what, how well sign-ins and email are protected, where files live and who they are shared with. A good one is read-only, ends in written findings ranked by risk, and gives you a prioritized plan. Before you ask anyone for one, you can run a short self-check of your own, and we include one below.

Why an assessment is worth doing

Most small firms set up Microsoft 365 once and then add to it for years. Licenses pile up, former staff keep accounts, sharing settings drift, and nobody is sure which security features are actually on. None of this is unusual, but it means you may be paying for things you do not use and missing protections you already own.

An assessment turns that uncertainty into a list. It tells you what is fine, what is risky, what is wasteful, and what to fix first. It is also useful evidence when an insurer, a client or an auditor asks how your systems are protected.

What a Microsoft 365 assessment covers

Scope varies by provider, but a thorough review usually looks at these areas:

Licensing fit and waste
Which plans you own, who is assigned to them, unassigned or duplicate licenses, and whether your plan matches what you actually need. Paid licenses on former employees are a common finding.
Identity and admin roles
How many people hold Global Administrator or other powerful admin roles, whether admins use separate accounts for admin work, and whether old or shared accounts can still sign in.
Multi-factor sign-in (MFA) coverage
Whether every account must use a second sign-in step, including admins and shared accounts, and whether that is enforced through Security Defaults or through sign-in rules (Conditional Access).
Email security and authentication
Whether your domain publishes the records that help other mail systems spot forged mail from you (SPF, DKIM and DMARC), whether automatic forwarding to outside addresses is blocked, and how spam and phishing filtering is configured.
SharePoint, OneDrive and Teams
How sites and teams are structured, who owns them, how external sharing is set, and whether files are shared with links that anyone can open.
Devices
Which computers and phones access company data, whether they are known to the business, and whether basic protections such as disk encryption and endpoint protection are in place.
Backup
Whether Microsoft 365 data is backed up by a separate service, or whether you are relying only on Microsoft's built-in retention.
Microsoft Secure Score
Microsoft's own measurement of how many recommended security actions you have taken, with a list of suggested improvements.

A self-check you can run without admin access

You do not need to be a Microsoft 365 administrator to answer these. Write down your answers, including "I don't know," which is a finding in itself.

1. Who in the company can add users, reset passwords or change settings? Can you name every person?
2. When an employee leaves, who removes their access, and how quickly does it happen?
3. Does everyone, including you, use a code or app prompt in addition to a password when signing in from a new device?
4. Do you know how many Microsoft 365 licenses you pay for each month, and how many people actually work here?
5. If an email from your own domain was forged, would the recipient's system have a way to tell? (If nobody has mentioned SPF, DKIM or DMARC to you, assume the answer is unclear.)
6. Where do client files live: SharePoint, OneDrive, Teams, a file server, personal Dropbox accounts, or all of them?
7. Can staff send a file link that anyone in the world can open without signing in?
8. Are company files accessed from personal phones or home computers?
9. If a mailbox or a SharePoint library were deleted or encrypted by ransomware today, how would you get it back, and has anyone tested that?
10. Has anyone looked at your Microsoft Secure Score in the past year?

If you answered "I don't know" to three or more, an assessment is likely worth the time.

Secure Score and the CIS Benchmark: useful, but not a grade

Microsoft Secure Score is a number in the Microsoft Defender portal that rises as you complete Microsoft's recommended security actions. Microsoft is clear that it measures adoption of controls, not the likelihood of a breach, and that not every recommendation suits every organization.

The CIS Microsoft 365 Foundations Benchmark is a community-developed set of configuration recommendations published by the Center for Internet Security. It is more prescriptive than Secure Score and is widely used as a reference point for Microsoft 365 settings. Neither one is a certification.

Two different NexJen assessments

We offer two fixed-scope engagements that people sometimes confuse. Both are advisory only: we take a read-only look at your tenant, analyze what we find, deliver written risk-rated findings and a roadmap, and walk you through them on a readout call. We make no changes to your tenant during either one.

Microsoft 365 Assessment & Optimization
A broad review of how your tenant is licensed, configured and used. Best when you want to cut waste, clean up accounts and admin roles, and understand how email, files and Teams are organized.
Security Posture & Compliance Assessment
A security-focused review benchmarked against the CIS Benchmark and Microsoft Secure Score. Best when an insurer, client or regulator is asking about your controls. It maps your gaps; it is not a certification or a formal audit.

If you are unsure which fits, start from the decision you need to make. Budget and cleanup questions point to the first. Questionnaires and security reviews point to the second.

A worked example

Take a hypothetical 18-person engineering firm on Microsoft 365 Business Standard. The owner's self-check turns up three "I don't know" answers: who the admins are, whether MFA covers everyone, and how files are shared with clients.

An assessment might find four Global Administrators, two of them former staff whose accounts were never deleted; MFA enforced for most users but not for a shared front-desk account; Anyone links turned on with no expiration; and five licenses assigned to people who left. The roadmap would rank those items by risk, note which fixes cost nothing, and flag where a plan change such as Business Premium would or would not be worth it.

Common mistakes

• Treating a high Secure Score as proof you are secure. It measures settings, not outcomes.
• Asking for an assessment and implementation in one undefined engagement, which makes the scope and the price hard to pin down.
• Fixing the easiest findings first rather than the riskiest ones.
• Not sharing the self-check answers with the assessor, which wastes discovery time.
• Letting the report sit. Assign each high-risk finding an owner and a date.

For the hands-on fixes that usually follow an assessment, see our guide to Microsoft 365 security best practices.

How NexJen can help

Both assessments are fixed-scope, fixed-fee engagements. We do not publish prices because the fee depends on your tenant size and scope; we quote it before you commit. They are open to any business, whether or not you use our managed services, and there is no long-term contract.

Implementation is separate. You can take the roadmap to your own IT team, have us quote the work as a fixed-fee project, or fold it into NexJen Essentials, our managed IT plan.

Common questions

Will an assessment change anything in my Microsoft 365 tenant?

Not with us. Our assessments use read-only access and make no changes. Any fixes are quoted and scheduled separately.

How long does a Microsoft 365 assessment take?

It depends on tenant size and scope. We agree the timeline when we quote the engagement.

Is a security assessment the same as a compliance certification?

No. Our Security Posture & Compliance Assessment benchmarks your settings against the CIS Benchmark and Microsoft Secure Score. It is not a certification or audit.

Do I need to be a managed IT client?

No. Our consulting engagements are open to any business running Microsoft 365.

Want a clear picture of your tenant?

Our Microsoft 365 assessments are read-only, fixed-fee engagements that end in written findings and a prioritized roadmap. Fees are quoted from your tenant size and scope.

Want a second opinion on your setup?

Start with a free Security Snapshot. We'll tell you honestly what we find and whether we can help.