Microsoft’s latest AI bundles revive a familiar enterprise challenge: paying for capabilities that only a subset of employees will use meaningfully. The dynamic itself is not new. For decades, Microsoft has expanded its position inside the enterprise by combining high-demand capabilities…
The EA Renewal Deadline Isn’t Your Deadline.
Last week I sat in on a renewal review with a procurement team. A Microsoft proposal was open on the screen. In the corner sat an expiry date, a few days out. The room had already shifted around that date. Every…
Microsoft True-Up: Enterprise FAQs
Understanding Microsoft True-Up, True-Down, and Contract Basics Can I reduce (true down) my Microsoft 365 subscriptions, and when? Yes. On your Enterprise Agreement anniversary, you can true down: Additional Online Services (e.g., Visio, Project, Power Apps, Dynamics, M365 F3) to as…
Microsoft’s July 1st Pricing Changes Means More Than Higher Costs.
Beginning July 1, 2026 Microsoft will increase pricing across several commercial plans: Office 365 E3, Microsoft 365 E3, Microsoft 365 E5, frontline licensing, and business plans. Microsoft attributes the increases to expanded capabilities tied to AI integration, security tooling, Intune management,…
When Your SAM Lead Is Out, Is Your Team Ready?
Vacation season exposes a SAM risk most enterprises never plan for. A vendor sent a True-Up request on a Tuesday. Moderate ask, tight window. The person who owned the software asset management position was in Costa Rica until the following Monday….
Microsoft Copilot: Why Enterprises Are Backing Out.
Over the past several months, I’ve had the same conversation with multiple large organizations. They adopted Microsoft Copilot with genuine enthusiasm, assigned licenses, ran internal communications, and waited for productivity gains to show up. For most of them, the gains never…
AI Spend Governance Starts With Token Consumption.
Real life scenario: a $500,000 charge landed on an invoice from a single query run without guardrails. The team had no visibility until after the fact. The vendor refunded most of it, but not all. This story came up in three…
When “More Licenses” Creates Microsoft Compliance Risk.
A company discovers gaps in its Microsoft licensing position, so the response feels obvious: Buy more CALs. Usually Device CALs. Sometimes User CALs. Often far more than the environment appears to require. The assumption is simple: if the organization owns more…
Microsoft EA Renewal Negotiation: The 30-Year Playbook.
I spent 8 years inside Microsoft selling the Enterprise Agreement before I started helping clients negotiate against it. The Microsoft EA renewal negotiation playbook has not changed in 30 years. Every renewal walks into the same machine. Most clients do not…
Your Microsoft EA Proposal Has a Math Problem.
A mid-size enterprise received two Microsoft EA proposals at renewal. One was built around Microsoft 365 E3, the other around Microsoft 365 E5. The M365 E5 package was quoted at roughly $8M per year. The M365 E3 package came in at…