How to Conduct Effective Microsoft 365 Security Assessments for MSP Prospects

Summary

Offering security assessments enables MSPs to demonstrate their value to potential long-term prospects. But conducting them manually against recognized security frameworks like CIS is slow and resource-intensive. MSPs following this approach must often sell assessments before attempting to sell managed services, complicating their conversion process. inforcer changes the economics by enabling streamlined onboarding and one-click assessments against recognized security standards that take minutes rather than hours. This allows MSPs to offer free security assessments as door-openers that win new business.

When your MSP is trying to win new business, offering security assessments can be a compelling way to get in the door. It helps demonstrate value before you ask for a long-term commitment to managed services.

Detailed tenant assessments and reports tell your prospective customers:

• Where their Microsoft 365 environments are falling short
• Which features they’re paying for but not using
• What the gaps between their current postures and best practices actually look like

It’s concrete, relevant, and hard to argue with. Better still, it frames the conversation about ongoing managed services as a natural next step instead of a sales pitch.

The problem is that manually conducting security assessments takes time and resources. This creates a practical conflict: the thing you should be using to attract new business ends up being something you have to charge for just to cover the associated costs. Fortunately, there’s a better way.

The right tooling can allow MSPs to conduct full Microsoft 365 security assessments in minutes instead of hours or days. This eliminates the vast majority of the costs involved, enabling you to offer assessments as free pre-sale offerings that still deliver genuine insight.

Demonstrating your value this way makes prospects much more receptive to conversations about longer engagements.

Why Security Assessments Are the MSP’s Best Door-Opener

Bringing the Receipts to Security Conversations

Security is the most urgent technology concern for most SMBs right now. Breaches are more frequent, more costly, and more visible than ever before. That creates opportunities for MSPs who can speak credibly about risk and how to mitigate it.

Security assessments are the clearest way to demonstrate what better looks like. Rather than asking a prospect to take your word for the value of managed services, you show them the current state of their environment in plain terms: what’s misconfigured, what’s missing, and what that means for their exposure.

When the evidence is sitting right in front of them, the conversation about what to do next becomes much easier to have.

Establishing Credibility

The value of an assessment also extends beyond the content of the findings. Assessments position your MSP as the expert in the room from the very first interaction. You’re not there to pitch; you’re there to help. That changes the dynamic and tends to produce better outcomes.

Meaningfully Improving ROI

For customers with Microsoft 365 environments, security assessments can also unlock compelling potential savings. Many SMBs are already paying for Microsoft 365 Business Premium without making full use of what’s included.

Intune, Defender for Business, Entra ID P1, and Conditional Access all come with this license, but they often remain unconfigured. Customers end up purchasing unnecessary third-party antivirus, email protection, and device management solutions, effectively paying twice for tools they may not even know they already have.

A security assessment allows your MSP to identify this oversight and makes your managed services pitch much more straightforward: the customer is already paying for the protection. You’re just offering to make it work.

The Problem With Manual Assessments

The logic of using security assessments as door-openers is fairly obvious. The execution, historically, is where many MSPs run into trouble.

Conducting a manual Microsoft 365 security assessment involves more steps than most people expect, and each one takes time.

Account Creation

Before you can even begin looking at a prospect’s environment, someone needs to create an admin account for you to use. That means:

• Coordinating with the prospect
• Provisioning the account
• Verifying access

This process can take hours on its own, before the true assessment work even starts.

Benchmarking

Once you’re in, assessing the tenant against a recognized framework is a substantial task. Evaluating a tenant against the CIS Microsoft 365 benchmark, for example, typically means:

• Working through a lengthy spreadsheet
• Manually checking each control
• Documenting your findings as you go

Done properly, this frequently requires six to eight hours per tenant. That’s most of a working day to run a single assessment for a single prospect.

At that rate, most MSPs can’t afford to offer security assessments for free. The cost in billable time is too high, which means they end up charging for the assessment. And charging for the thing you’re using to attract new business creates an awkward dynamic off the top, because the prospect has to commit before they’ve seen any result. It becomes the opposite of the rapport-building technique a security assessment is supposed to be.

See Also: inforcer Achieves CIS Benchmark Certification

Making Microsoft 365 Security Assessments More Cost-Efficient

The solution is for MSPs to move away from manually conducting security assessments and embrace tooling that streamlines the process. Leading multi-tenant management platforms like inforcer allow an MSP to:

• Considerably reduce the billable time required for the entire assessment workflow
• Improve the accuracy of assessments by reducing the potential for manual errors
• Simplify reporting with engaging, client-ready summaries and detailed breakdowns

This approach makes the free assessment model not just viable for MSPs but genuinely practical and repeatable. Here’s a chart that explains the difference:

Self-Service Onboarding

The process starts with onboarding. Rather than requiring your MSP to manually create an admin account in the prospect’s tenant, inforcer generates a secure link that the prospect can use to onboard themselves. They sign in with their own credentials, accept the terms, and their tenant is temporarily onboarded into inforcer. It’s that simple.

There’s no account provisioning, back-and-forth, or shared credentials required. For your MSP, this completely eliminates a time-consuming step in the process.

Conducting Single-Click Assessments

Once the tenant is onboarded, inforcer allows you to run assessments against a variety of recognized security frameworks in a single click. Work that used to take six to eight hours of manual checking now takes minutes. You’re also able to view alignment scores showing how each tenant compares to your chosen benchmarks without leaving your dashboard.

The Benefits of Smoother Security Assessments

• Reducing objections: When an assessment takes minutes instead of hours, the cost calculation changes entirely. Offering a free assessment to a qualified prospect becomes a sustainable strategy to win their business instead of a loss leader.
• Priming prospects for future pitches: Prospects are more willing to agree to something that costs them nothing and delivers immediate value. And when your MSP arrives at the eventual conversation around managed services, you come with concrete, credible evidence of what the prospect stands to gain.
• Building brand acclaim: Even in cases where a prospect doesn’t convert immediately, a well-run, professionally delivered free assessment leaves a lasting impression. That often translates into projects or referrals further down the line.

What to Evaluate in a Prospect’s Microsoft 365 Environment

Not all misconfiguration is created equal. A good security assessment doesn’t just compile a list of gaps; it identifies which gaps matter most and helps the prospect understand why.

These are some of the areas worth examining in any Microsoft 365 security assessment.

Learn More: Building a Productized Microsoft 365 Security Offering for Your MSP

Identity and Access Controls

Entra ID configuration is often the most revealing place to start. Many SMBs have not enabled multi-factor authentication across all users, are not enforcing Conditional Access policies, or are running with overly permissive admin roles. Each of these represents a meaningful security risk, and each is a direct consequence of underutilizing features that Business Premium includes.

Endpoint Protection and Device Management

If the prospect is on Business Premium and Defender for Business isn’t configured, or Intune hasn’t been deployed, they’re leaving core endpoint protection on the table. Device compliance policies, configuration profiles, and enrollment restrictions are foundational to a defensible security posture—and all of them are available at no additional cost on Business Premium. 

Email and Collaboration Security

Microsoft Defender for Office 365 provides protections against phishing, malware, and malicious links. Safe Links and Safe Attachments policies are commonly left at default or disabled entirely. These are low-effort to configure and high-impact for everyday risk reduction.

Data Protection and Compliance Settings

Sensitivity labels, data loss prevention policies, and information protection settings are frequently unconfigured in SMB tenants. For businesses in regulated industries or handling sensitive customer data, these gaps carry real compliance risk in addition to security risk.

Secure Score Baseline

Microsoft Secure Score gives every tenant a quantified measure of their security posture against Microsoft’s own recommendations. It’s a useful reference point in any assessment, as it makes the current state legible and provides a natural metric for tracking improvement over time. inforcer’s ability to assess a tenant against recognized security standards maps well onto Secure Score, giving MSPs a structured, credible benchmark to present to prospects.

Identifying Quick Wins vs. Long-Term Projects

One of the most valuable things an assessment can do is help a prospect understand the difference between what can be fixed quickly and what requires a longer-term investment. Framing findings this way serves the sales conversation as much as the security one—it gives the prospect a sense of momentum rather than an overwhelming list of problems.

Quick wins are low effort, high-impact security improvements that can be addressed immediately after the assessment. They’re most useful for building early confidence with new or prospective customers.

Long-Term Projects require significant configuration work, but typically form the foundation of an ongoing managed services engagement because they give your MSP room to demonstrate essential expertise that evolves alongside the customer’s needs.

Here are some examples of each:

Turning Assessment Findings Into Compelling Reports

The quality of an assessment is only as useful as the quality of the report that communicates it. A technically accurate set of findings buried in dense output is much harder to act on than a clear, well-structured document that tells a story.

The most effective assessment reports share a few common characteristics. They lead with headlines: overall security posture, the most significant gaps, and the relative urgency of each. They include plain-language executive summaries rather than confusing technical jargon, and they connect the findings to business outcomes that matter to the prospect: their breach risk, the costs of underutilizing their license, and their compliance exposure.

inforcer’s built-in reporting capabilities produce structured, customer-ready documentation benchmarked against recognized standards.  This enables your MSP to focus on context and recommendations rather than data compilation and document formatting.

From Assessment to Ongoing Managed Security Service

The security assessment should be the beginning of your relationship with a new prospect, not a one-off project. Your goal is to use the findings as the foundation for an ongoing managed security engagement, and the transition is most natural when the assessment has been structured with that endpoint in mind.

The quick wins identified during the assessment are also natural early deliverables. Delivering them promptly and demonstrating the improvement (through a follow-up Secure Score comparison, for example) reinforces your value in the relationship before the ink is fully dry on your contract.

The longer-term projects provide the structure for the ongoing engagement. A managed services agreement built around delivering those improvements over time gives the customer a clear sense of what they’re getting and gives your MSP a natural rhythm of delivery and review.

inforcer supports both phases. Once a new customer’s tenant is under management, inforcer’s multi-tenant platform allows MSPs to standardize configurations, monitor for policy drift, and run ongoing assessments to track progress over time. The same tool that made the pre-sale assessment fast and credible becomes the operational backbone of the managed services delivery.

Learn More: How to Manage Configuration Drift Across Multiple Microsoft 365 Tenants

Start More Conversations With Less Overhead

Security assessments are one of the most effective tools MSPs have for building trust with prospects and converting conversations into contracts. The barrier has always been the time they require. But with inforcer, that barrier no longer exists.

Using inforcer allows you to offer thorough, framework-aligned Microsoft 365 security assessments free of charge because they take minutes, not hours. Your prospects onboard themselves, you run each assessment in a single click, and the results give you exactly what you need to make a compelling case for providing managed security services.

Book your demo today to see how inforcer can work for you.