Why Licensing Strategy Starts with the Right Questions

By Lucy Mitchell, Licensing Strategist & Certified Software Asset Manager, Synergy Technical

Every day, I help customers make licensing changes: adding users, adjusting SKUs, scaling up or down. But the real work isn’t just about clicking through a portal—it’s about asking the right questions before you do anything at all.

If you're ever unsure about what Microsoft license you need, you’re not alone. I talk to customers all the time who aren’t exactly sure what’s included in their plan, whether they’re covered for security or compliance features, or if there’s a more cost-effective way to achieve the same outcome.

That’s where I come in. My job is to make sure your licensing is doing what you need it to do—nothing more, nothing less.

Read The Ultimate Guide: What is Microsoft CSP?

Licensing Shouldn’t Be a Guessing Game

Microsoft’s SKU catalog is deep. There are bundles, add-ons, tiers, feature gates—some of which sound almost identical. It’s not always obvious what you’re getting or what you actually need.

For example:

• Customers often ask, “Do I need Microsoft Defender for Endpoint Plan 1 or Plan 2?”
• Or, “If I already have Microsoft 365 E5, do I also need a separate compliance add-on?”
• Or, “Why am I being billed for something I thought was included?”

These aren’t just billing issues—they’re business issues. Choosing the wrong SKU might mean you’re missing key features, or worse, paying for functionality twice.

What I Ask Customers Before Recommending Anything

Before I process a license change, I always take a moment to confirm a few things:

• What are you trying to accomplish? Not just “I need email,” but “I need email with DLP and encryption.”
• Who are the users? Different roles often require different licenses. Frontline workers vs. IT admins shouldn’t be licensed the same way.
• Do you already own this feature in another SKU? Microsoft loves bundling—and it’s easy to double-pay without realizing it.
• Are there better ways to align cost with usage? Sometimes a switch to CSP gives more flexibility than what the customer had in an EA.

Because here’s the truth: I don’t want you to have the most licenses—I want you to have the right ones.

Small Changes, Big Impact

One of the most satisfying parts of my job is seeing how small adjustments in licensing can solve big problems:

• One customer was paying for an expensive security add-on, not realizing it was already included in their E5 license. We saved them thousands just by removing the duplicate SKU.
• Another needed to meet compliance requirements quickly. We identified the right set of tools in Microsoft Purview and had them licensed and ready the same day.
• And when billing doesn’t look right? I’ll help untangle it and make sure you’re only paying for what you actually use.

I work on licensing strategy all day, every day. I see the patterns. I know the SKU matrix. And I know how to turn confusion into clarity.

If you ever feel unsure about what you're licensed for—or what you're missing—reach out. You don’t need to figure it out alone. That's what I’m here for.

Ready to transform your licensing strategy? Contact us today to schedule a consultation, learn more about the Microsoft CSP licensing benefits, or start optimizing your Microsoft cloud services with a trusted partner by your side. Let’s modernize your cloud journey together!