Powered by Microsoft Copilot, Copilot Studio, and Azure, I’ve been quietly building something different:
a License-First Architecture for Microsoft 365.
Instead of treating licensing as a procurement task, I’m treating it as an architecture layer where eligibility, prerequisites and risk are mapped before we talk about SKUs and discounts.
Most Microsoft 365 licensing conversations are happening one layer too high.
Cost is not the real problem.
Eligibility is.
Over the last year, I kept seeing the same pattern:
- Copilot initiatives stalling
- Security projects getting re-scoped late
- Procurement and IT talking past each other
- “Surprise” gaps discovered after contracts were signed
Not because teams chose the wrong product —
but because certain scenarios were never licensed to begin with.
The uncomfortable truth:
Many Copilot, security, and compliance plans fail before deployment,
at the license + prerequisite layer.
So instead of building another price calculator,
I built an internal decision engine that maps:
Requirements → Eligibility → Risk → Cost → Proof
Using only Microsoft documentation and Product Terms —
no opinions, no selling, no shortcuts.
What surprised me wasn’t the numbers.
It was how often the answer came back as:
“You are not eligible to do what you’re planning — yet.”
I’m not publishing the engine.
Tools without context create more damage than clarity.
But if you’re planning Copilot, E5, or major security changes this year,
it’s worth pressure-testing assumptions before signatures and renewals.
Clarity is cheaper than correction.
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