Executive Summary
With 90 days remaining before your Microsoft Enterprise Agreement renewal, the pressure intensifies. Microsoft's sales team will ramp up urgency — expect "last chance" offers, quarter-end deadlines, and pressure to sign quickly. A disciplined CIO or procurement leader knows better: these final three months are precisely when structured preparation delivers the greatest commercial advantage.
This guide provides a week-by-week framework for the final 90-day sprint — from dissecting Microsoft's initial proposal and modelling negotiation scenarios, through executive alignment and legal review, to licence clean-up and structured negotiation scheduling. Organisations that follow this playbook consistently achieve 15–25% better outcomes than those that enter the final stretch unprepared. The difference between a good deal and a great deal is almost always determined by what happens in these last 90 days.
Proposal Evaluation
Dissect Microsoft's renewal proposal line by line — comparing quantities, SKU pricing, and discount levels against your current EA and actual usage data.
Scenario Planning
Define best-case, target, and walk-away outcomes before you sit at the table. Know your boundaries and your fallback position.
Legal Review
Have counsel review all draft terms — especially new AI/Copilot clauses, data residency provisions, and audit rights — with redlines prepared before negotiations begin.
Licence Clean-Up
Eliminate shelfware, right-size user counts, and freeze the environment to present Microsoft with a lean, accurate renewal scope.
Evaluate Microsoft's Renewal Proposal
At the 90-day mark, you should have Microsoft's initial renewal proposal in hand. Now is the time to scrutinise that offer with the same rigour you would apply to any multi-million-pound investment decision. Every line item in that proposal is negotiable — but only if you identify the issues first.
Compare Against Your Current EA
Cross-reference every line item in the renewal proposal against your existing entitlements. Is Microsoft quoting more licences than you currently have? Have they upgraded you to a higher-tier product (e.g., E5 where you had E3) without your request? Are any previously included services now appearing as paid add-ons? Document every discrepancy — these are your first negotiation targets.
Identify Price Increases and Eroded Discounts
Flag every cost increase relative to your current EA. Common tactics include: removing previously granted discounts, applying a new "standard uplift" (typically 5–8%), introducing mandatory add-ons for security or compliance features that were previously bundled, and reclassifying products under different SKUs with higher list prices. Each of these must be challenged individually — do not accept a blanket "costs have gone up" narrative.
Uncover Hidden Add-Ons and Upsells
Look for products or services in the proposal that were not in your previous agreement. Common upsells include: Microsoft 365 Copilot licences, advanced security and compliance add-ons (E5 Security, E5 Compliance), Azure AI services, and Defender suite components. Determine whether each addition addresses a genuine, funded need — or is simply vendor-driven padding that inflates the total cost. If you did not ask for it, challenge it.
Lock the Renewal Scope
After identifying unnecessary components, communicate your exact requirements to Microsoft in writing. If you need 800 M365 E5 licences but were quoted 1,000, insist on a revised proposal reflecting the correct quantity. Freezing scope early prevents Microsoft from using inflated baselines as the starting point for "discount" calculations — a common tactic where a 20% discount off an inflated number still costs more than full price on the correct number.
Energy Company: The Phantom Licence Uplift
Situation: A UAE-based energy company received a renewal proposal from Microsoft quoting 4,200 M365 E5 licences. Their actual deployed count was 3,400. Microsoft's sales team presented a "12% discount" on the proposal.
Analysis: Redress Compliance identified that the 800 phantom licences inflated the baseline. The "12% discount" on 4,200 seats actually cost more than full price on the correct 3,400 seats. Additionally, an E5 Security add-on had been bundled without request.
Takeaway: Always validate Microsoft's proposed quantities against your actual deployment data. A discount on an inflated baseline is not a discount — it is a pricing strategy.
Scenario Planning: Define Your Boundaries
With the proposal dissected, turn to scenario planning. Defining your desired outcomes and walk-away boundaries before you sit at the negotiation table is what separates disciplined procurement from reactive deal-making.
| Scenario | Key Characteristics | Example Outcome |
|---|---|---|
| Best Case | Deep discount; highly favourable terms; new concessions secured | ~15% cost reduction versus current EA, plus flexible terms (true-down rights, price caps, free pilot licences) |
| Target Case | Acceptable deal meeting key objectives; minimal cost increase | 0–5% increase with bundle discount on new products; improved contract flexibility; Azure credits included |
| Walk-Away | Minimum acceptable terms; below this threshold, delay or explore alternatives | No more than 5% cost increase; if higher or if critical terms (true-down, price lock) are refused, pause and invoke fallback plan |
🎯 Fallback Plan: What If You Cannot Reach Agreement?
- Short-term EA extension: Negotiate a 30–60 day extension of the current agreement to continue negotiations without a coverage gap.
- Interim CSP or MCA coverage: Shift critical workloads to month-to-month Cloud Solution Provider licences as a bridge while finalising terms.
- Competitive exploration: Signal genuine interest in Google Workspace, AWS, or other alternatives to create leverage. Even a credible evaluation process changes Microsoft's pricing calculus.
- Partial renewal: Renew only the essential product lines now and defer negotiation on discretionary components (Azure, Copilot, Dynamics) until terms improve.
Executive Leadership Briefing
In the final 90 days, keeping your executive leadership aligned is not just good practice — it is a critical negotiation defence. Microsoft's enterprise sales teams are trained to engage C-level executives directly, creating urgency ("your renewal is at risk") or dangling strategic vision ("let's discuss your AI transformation roadmap") to pressure a quick signature that bypasses procurement's negotiation stance.
Brief CIO and CFO on Offer vs Targets
Provide a clear, concise comparison of Microsoft's proposal against your target scenario. Highlight major gaps, hidden cost increases, and the specific terms you intend to negotiate. Executives make better decisions with data, not with Microsoft's sales narrative.
Secure Executive Backing for Push-Back
Confirm that leadership fully supports your negotiation stance — including the willingness to delay signing if Microsoft's offer does not meet your minimum terms. If the C-suite is aligned, Microsoft cannot divide and conquer by going around your negotiation team. This is the single most important thing you can do at the 90-day mark.
Agree on Escalation Protocol
Decide in advance how you will escalate if negotiations stall. A well-timed CIO-to-Microsoft VP conversation can break deadlocks — but only if it is planned, not reactive. Agree on the trigger points (e.g., "if we haven't reached target terms by T-30, the CIO engages Microsoft's regional VP") and ensure the executive is briefed on what to ask for.
"The single most common reason organisations accept suboptimal Microsoft EA terms is not poor negotiation — it is a C-level executive who signs under pressure because procurement failed to brief them on the strategy and walk-away position."
Legal Review of Proposed Terms
With 90 days remaining, have your legal counsel review Microsoft's draft agreement in detail. The commercial terms change between renewals, and new clauses — particularly around AI services, data handling, and audit rights — can introduce significant risk if accepted without scrutiny.
🎯 Priority Legal Review Areas
- AI and Copilot terms: Microsoft may include clauses governing data usage, output ownership, liability, and privacy for AI services like M365 Copilot. Ensure these are understood and acceptable. If not, prepare specific redline language.
- Data residency and privacy: Verify that the agreement meets your data residency requirements (e.g., EU Data Boundary commitments). Check GDPR, CCPA, or sector-specific privacy provisions are explicitly covered.
- Audit rights: Scrutinise Microsoft's audit clauses. Push for reasonable notice periods (minimum 30 days), defined scope limitations, and caps on audit frequency. Overly broad audit rights create ongoing compliance risk.
- True-up and true-down mechanics: Confirm the contractual mechanics for annual adjustments. Can you reduce licence counts (true-down) or only increase (true-up)? This distinction is worth millions over a 3-year term for organisations with fluctuating headcount.
- Termination and exit provisions: Review what happens if you need to exit the EA early. Understand data extraction rights, transition periods, and any penalties. See Negotiating Termination and Renewal Options.
For each issue identified, prepare specific redline language — not just objections. Presenting alternative wording to Microsoft increases the likelihood of a favourable adjustment and demonstrates that you are negotiating from a position of preparation, not reaction.
Optimise and Lock Licence Entitlements
The final 90 days are your last opportunity to clean up your licensing environment so that you are not paying for anything unnecessary at renewal. A lean, accurate licence profile is the foundation of a strong negotiation position.
Freeze and Stabilise the Environment
Avoid major changes to user counts or deployments in the final 90 days. Postpone large-scale onboarding or new product rollouts so your usage remains stable and quantifiable. A moving target makes it impossible to negotiate precise licence counts — which is exactly what Microsoft's sales team prefers.
Eliminate Shelfware
Conduct a final sweep for unused licences — idle M365 seats, undeployed Dynamics modules, dormant Power Platform licences, inactive Azure subscriptions. Remove them from your entitlement count and ensure Microsoft's renewal proposal reflects these reductions. Every eliminated shelfware licence directly reduces your renewal baseline and annual cost.
Right-Size Product Tiers
Evaluate whether users on premium tiers (E5, F5) genuinely need those capabilities, or whether a lower tier (E3, F1) would suffice. Downgrading 500 users from E5 to E3 saves approximately $120K annually at typical enterprise pricing. This analysis should be completed before you enter negotiations so that your target licence profile is fully defined.
Professional Services Firm: The $840K Shelfware Clean-Up
Situation: A US-based professional services firm with 6,000 employees was preparing for EA renewal. A Redress Compliance licence audit discovered: 1,200 M365 E5 licences assigned to users who only used email (E1 functionality), 340 Dynamics 365 Sales licences with zero logins in the past 12 months, and 80 Power BI Pro licences unused since deployment.
Action: Before renewal, 1,200 users were downgraded from E5 to E3, the 340 Dynamics licences were removed, and 80 Power BI Pro licences were eliminated.
Takeaway: Licence clean-up before renewal is the single highest-ROI activity in the entire renewal process. Every eliminated shelfware licence reduces your baseline — and all future percentage-based pricing builds on that baseline.
Schedule and Structure Negotiation Meetings
With 90 days remaining, bring structure to the negotiation process. Unstructured, ad hoc conversations with Microsoft's sales team benefit them, not you. A disciplined cadence keeps momentum on your terms.
Establish a Weekly Negotiation Cadence
Schedule weekly or biweekly calls with Microsoft's account team, with your internal stakeholders available for rapid turnaround on decisions. Steady meetings maintain momentum and ensure no week passes without progress. Document every meeting's outcomes and action items in writing.
Align Key Milestones with Microsoft's Fiscal Calendar
Microsoft's fiscal year ends in June; quarters close in September, December, and March. If your renewal coincides with a quarter-end, leverage this timing — Microsoft's sales teams are under maximum pressure to close deals and have the most flexibility to offer concessions. Signal that you are targeting a close if your requirements are met — creating mutual urgency on your terms.
Pre-Plan Escalation Triggers
Define specific dates by which you will escalate if progress stalls. For example: "If we have not agreed on pricing by T-45, the CIO engages Microsoft's regional VP." "If legal terms are unresolved by T-30, we request a 60-day extension and pause signing." Having predetermined escalation points prevents panic decisions in the final weeks.
The 90-Day Countdown Timeline
| Timeframe | Action | Owner |
|---|---|---|
| T-90 to T-75 | Receive and dissect Microsoft's renewal proposal line by line. Compare against current EA and actual usage data. | Procurement + IT Ops |
| T-75 to T-60 | Complete scenario planning (best/target/walk-away). Finalise shelfware analysis and licence right-sizing. | Procurement + Finance |
| T-60 | Executive leadership briefing. Secure C-suite alignment on strategy, stance, and escalation protocol. | CIO/CFO + Procurement Lead |
| T-60 to T-45 | Submit revised scope and counter-proposal to Microsoft. Begin structured negotiation meetings. | Procurement Lead |
| T-45 to T-30 | Active negotiation rounds. Legal review of draft terms with redlines prepared. | Procurement + Legal |
| T-30 | Legal review complete. Internal approvals circulated. Extension letter requested (contingency). | Legal + Finance |
| T-30 to T-14 | Final negotiation push. Escalate to VP level if pricing/terms not at target. | CIO + Procurement |
| T-14 to T-7 | Contract verification (SKU-level). One-page executive summary for final sign-off. | Procurement + Legal |
| T-7 to T-0 | Final approvals. E-signature execution. Internal communication plan activated. | All stakeholders |
"Organisations that start the 90-day countdown with a complete licence audit, defined scenarios, and executive alignment consistently achieve 15–25% better commercial outcomes than those that begin negotiations by responding reactively to Microsoft's initial proposal."