This blog was originally published by Softchoice, a World Wide Technology co.

It happens quietly. A batch of new hires join the org. They need Teams. Another team wants Visio. Sooner than later it's time for renewal, and your IT team, under pressure from many directions, ticks the same basic boxes as last year.

The licenses are renewed. Some are adjusted. Mission accomplished.

Over time, this reactive approach leads to a mix of Microsoft 365 licenses that meet the basic needs of end users. Okay.

But if this sounds like you, it's likely you're not meeting the full value creation potential of your Microsoft 365 investments due to a reactive approach.

Why a reactive approach to Microsoft 365 licensing is costing you opportunity

In the ideal world, you have advance knowledge of Microsoft products and services that are changing or going end-of-life (EOL). You always choose the best fit technology stack and licenses for everyone in your org. You go to sleep safe in the knowledge your security posture and data are ready for the AI-powered future.

In a lot of organizations, though, managing Microsoft 365 licenses is still a reactive process. It's something IT teams think about at key points in the contract cycle or when a procurement request triggers an action.

There's rarely time to stop and think, "Are the licenses we're buying actually aligned to what the business needs today? What about next year? Three years from now?"

This reactive mindset persists for a few understandable reasons. Microsoft's ecosystem evolves constantly, with new bundles, features and entitlement rules coming into play all the time.

A lot of IT teams are under pressure to do a lot with little to no time and limited resources, leaving no space to think about strategies for buying Microsoft 365.

Keeping up with everything new at Microsoft takes more time than they have in a day. Many had good processes once upon a time, but they've fallen by the wayside. This is no surprise, with the Microsoft Work Trend Index finding that 80 percent of employees and leaders lacking enough time to get their work done.

As new and important changes to generative and agentic AI enter the Microsoft product ecosystem, falling behind takes on a greater dimension of risk. That said, making big SKU changes, moving workloads around, or consolidating titles can feel disruptive and therefore risky.

Nonetheless, by sticking to "status quo" you're also likely overprovisioning and underusing the licenses you have, and failing to take advantage of new capabilities, features and consumption options coming out of Microsoft.

How proactive planning for Microsoft 365 can have a big impact on the business

In a sense, any Microsoft 365 license is only as valuable as its connection to a real-world business outcome.

At WWT and Softchoice, we encourage customers to adopt a proactive approach that considers:

  • Your business roadmap, current user roles and projected growth
  • Microsoft's roadmap for products, pricing and bundling
  • New innovations in AI, security, Azure cloud infrastructure and services
  • Organizational priorities, structure and workforce composition

When license usage aligns to real world needs, rather than best guesses or past circumstances, the payoff comes in less spend wasted on licenses or features that aren't used and higher adoption of the products you're paying for.

This in turn creates breathing space for all that innovation IT is supposed to be spearheading when they're not busy fighting fires and pushing break/fix tickets.

Here are just a couple of few hypothetical use cases:

  • A healthcare provider upgrades from E3 to E5 across its frontline workers, without realizing most of them only use basic email and Teams. A rightsizing effort saves them $300K per year.
  • A professional services firm renews Microsoft 365 Business Premium for every employee without considering that most consultants already had the tools they needed under another vendor's plan. A simple realignment reduces redundant spend by 20 percent.
  • A public sector organization isn't taking advantage of Microsoft's cloud migration funding programs because no one has time to find out whether they are even eligible. By aligning license planning with the Microsoft roadmap, they found the budget and funded their Teams Voice deployment.

What organizations often miss when decisions are renewal-driven

The challenge goes beyond simply buying too many licenses. It's really the opportunity cost paid in failing to optimize for organizational change.

This might look like expansion of remote work or adding new branch locations, shifts in workforce makeup, adoption shortfalls for some features, or new innovations from Microsoft around AI or security.

Just renewing existing licenses isn't just maintaining the status quo; it's leaving real business value on the table.

Here's what you can do right now:

  • Map your current license inventory to your workforce as it exists today. Are the right users set up with the right bundles? Are you overprovisioning frontline workers or seasonal staff?
  • Look ahead at the business changes you can anticipate in the next 12-18 months. Will job roles change? Will there be an uptick or down trends in remote or hybrid work? Will the org be launching new services or teams?
  • Keep an eye on what's new at Microsoft. Are there any new license types, bundles, or security tools you could make use of? Is there funding or migration support available?
  • Consider the total cost of ownership (TCO). Think about whether investing upfront in deployment, user onboarding, security configuration, training and ongoing support is worthwhile given the long-term value?

Of course, you don't have to do it alone.

Taking the next step

A smarter, more intentional "full value" approach to Microsoft 365 will do more than reduce cost and risk. It will open the door to genuine value for the business.

Transacting your Microsoft 365 under the Cloud Solution Provider (CSP) program, if you aren't already, adds further value in proactive support for license planning, uncovering funding opportunities, scenario modeling and insight into the Microsoft roadmap. This means fewer surprises, smarter choices, and better alignment between what you buy and where your business is going."

Ask yourself, "Is our current Microsoft 365 licensing process creating value, or just repeating what we've always done?" If the answer gives you pause, we'd love to talk. Let's explore how you can align what you buy to where your business is going and start realizing the full potential of Microsoft 365 with WWT and Softchoice.

Technologies