Microsoft EA Renewal Readiness Checklist
Renewing a Microsoft Enterprise Agreement (EA) is a high-stakes milestone for any large organization. These multi-year contracts determine your IT spend and capabilities for the next three years or more, so approaching renewal without preparation can lead to overspending or being locked into unfavorable terms.
CIOs, procurement leaders, and IT asset managers are aware that Microsoft will present its own agenda – often promoting new cloud services, bundles, or upgrades. To negotiate from a position of strength, you need a clear plan.
A structured Microsoft EA renewal checklist brings order to this complex process.
It ensures you cover all bases: analyzing your current usage, forecasting future needs, aligning internally on strategy, and exploring alternatives.
By following a checklist-driven approach, you transform the renewal from a rushed administrative task into a strategic opportunity.
The result is better renewal readiness – meaning fewer surprises, stronger negotiating leverage, and an EA that truly fits your organization’s requirements.
In this article, we provide a practical EA renewal template to guide your team step-by-step toward a successful renewal.
For more templates and playbooks, read our overview of Microsoft EA Negotiation Templates and Playbooks.
Purpose of the Renewal Checklist
What it is:
The renewal readiness checklist is a comprehensive planning tool that outlines all the critical steps and considerations for your Microsoft EA renewal.
Think of it as a project roadmap that ensures nothing falls through the cracks – from initial internal assessments all the way to final negotiations. It’s not just a to-do list, but a framework to manage the renewal process methodically.
Who it’s for:
This checklist is designed for the core team handling the EA renewal. Typically, that includes CIOs or IT directors, procurement and sourcing leaders, IT asset managers, licensing specialists, and often input from finance (CFO or controllers) and legal counsel; in short, anyone responsible for budgeting, managing, or approving Microsoft licensing will benefit.
The checklist keeps all these stakeholders on the same page, facilitating executive alignment and cross-functional collaboration. Whether you’re a seasoned IT procurement manager or a CIO overseeing your first EA renewal, the checklist provides clarity on roles and tasks.
When to use it:
Start using the checklist well before your EA expiration date. Ideally, you begin planning and preparations 6–12 months in advance (for very large enterprises, even earlier). However, if your renewal is closer, don’t worry – the checklist remains invaluable, even 3–6 months out or in the final weeks, for last-minute readiness checks.
Use it as a timeline guide: many organizations will refer to the checklist at key intervals leading up to renewal (for example, at 6 months, 3 months, and 1 month out) to ensure they’re on track.
Essentially, the moment you start thinking about an upcoming EA renewal is when you should pull out this checklist.
It will guide your planning meetings, task assignments, and decision-making processes all the way up to the signing of the new agreement.
The Renewal Checklist ✅
Below is a Microsoft EA renewal checklist with key action items.
Each checklist item is marked with a ✅ and includes a brief explanation to help you execute it effectively.
Use these as objective checkpoints to measure your renewal readiness:
- ✅ Current Usage Analysis: Evaluate your organization’s current Microsoft license usage and compare it to what you’re actually entitled to under your EA. This involves conducting a comprehensive review of all licenses, subscriptions, and cloud services currently in use. Identify any unused or under-utilized licenses (“shelfware”) – for example, unused Visio or Project licenses, or users assigned an expensive Office 365 E5 license who only use E3-level features. Also, pinpoint any areas where usage exceeds entitlements (to catch compliance issues early). The goal is to establish a clear baseline: know exactly what you have, what’s being used, and what isn’t. This data is critical for deciding what to renew, what to cut, and where to optimize before you enter negotiations.
- ✅ Forecasting Needs: Look ahead to the next agreement term (typically 3 years) and forecast your organization’s needs. Collaborate with business units and IT planners to project how your use of Microsoft products is likely to grow or change. Are you planning a major cloud migration to Azure? Do you expect a growth in user count or the opening of new offices? Any upcoming projects to deploy new Microsoft technologies (e.g., rolling out Dynamics 365, Power Platform tools, or an upgrade to Microsoft 365 E5)? Also consider industry trends – for instance, many companies are evaluating AI-powered add-ons, such as Microsoft Copilot. Estimate future license quantities and feature needs, and model the budget impact using Microsoft’s pricing (including any known price increases or adjustments). The output of this forecasting is a set of anticipated requirements and a budget range that your renewal should accommodate. Having this clear picture ensures you’re not just renewing what you had before, but right-sizing for where you’re going.
- ✅ Executive Alignment: Ensure that your leadership and stakeholders are aligned on the goals and parameters of the renewal. An EA renewal isn’t just an IT decision – it has company-wide financial and strategic implications. Early in the process, convene the key executives: your CIO, CFO, CTO, and relevant VPs or department heads who rely on Microsoft services. Define what a “successful renewal” looks like for your organization. Is it minimizing any cost increase? Enabling a cloud-first initiative? Upgrading security and compliance capabilities? Agree on priorities and deal-breakers. For example, leadership might set a target to keep budget growth under 5% or to include certain new software within a fixed spend. Executive alignment also means establishing an executive sponsor (often the CIO or CFO) who will back the negotiation strategy and be available to engage with Microsoft’s executives if needed. When top management is on board and unified in purpose, Microsoft’s sales teams will find it harder to divide and conquer stakeholders with last-minute pitches. Internal unity is a key asset – it ensures negotiating decisions stick and that you don’t agree to something internally unsanctioned under pressure.
- ✅ Internal Audits: Conduct an internal audit from two angles: license compliance and contract review. First, perform a license compliance check well in advance of the renewal. Verify that your usage of Microsoft software and services does not exceed your licensed quantities. If you do find any compliance gaps (for instance, more users in a software than you have licenses for), address them proactively now – reallocate unused licenses or purchase the needed ones quietly – rather than waiting for Microsoft to find them during renewal (which could weaken your position). Second, review your current EA contract terms and any relevant corporate policies. Note any clauses about notice periods (do you need to inform Microsoft or your reseller if you plan not to renew by a certain date?), price protections, or renewal options. Also, review past true-up records and ensure all documentation is in order. By auditing internally, you eliminate surprises. You’ll enter renewal talks with confidence that you’re fully compliant (removing a common pressure point Microsoft may use) and aware of your contractual rights and obligations.
- ✅ Microsoft Quotes and Proposals: As you approach the renewal window, engage with Microsoft (or your Licensing Solution Provider) to obtain official renewal quotes or a pricing proposal. Microsoft often provides a pricing workbook or quotes a few months before expiration – treat this as the starting offer, not the final deal. When you receive the quote, analyze it in detail by comparing it against your current spending and verifying that all the items align with your needs. Often, the initial quote may include upsell items (like higher-tier suites or additional products) that you didn’t ask for. Identify any discrepancies or unwarranted additions. For example, are they quoting you for Microsoft 365 E5 when you currently use E3 without justification? Are there cost increases that you can challenge or at least understand (maybe due to known price hikes)? Use your usage analysis and forecast data to evaluate the quote – if it suggests purchasing more licenses than your analysis says you need, flag it. This step involves gathering intel: you want to know Microsoft’s initial position. It also helps you formulate specific questions and counterpoints for negotiation. Remember, you don’t have to accept the quote as-is; every line item is potentially negotiable if you have the data to back your stance.
- ✅ Negotiation Playbook: Develop a negotiation game plan well in advance of sitting down with Microsoft’s sales reps. Your negotiation playbook should include clear objectives, tactics, and fallback positions. Start by defining your key goals (from the executive alignment step) in actionable terms – e.g., “achieve at least 20% discount on Office 365 E5 licenses” or “secure rights to reduce license count by 10% annually if needed.” Outline the concessions or trade-offs you’re willing to make: for example, you might be open to a modest Azure spend commitment if it yields better pricing, but only up to a certain budget limit. Assign roles for the negotiation meetings – determine who will lead discussions, take notes, handle financial details, etc. Anticipate Microsoft’s likely tactics: they might push for an early signature with a time-limited discount, bundle in new products like Security or AI features, or warn of price increases. Prepare counters for each: if they push product bundles, be ready with data on current utilization and whether those features are truly needed. If they warn about price hikes, have your benchmark or budget justification to push back. Benchmarking is another part of your playbook – if possible, gather information on what discounts similar organizations are getting, so you know if Microsoft’s offer is fair. Importantly, define your “walk-away” plan: what will you do if the deal on the table isn’t acceptable by your deadline? Having a credible plan B (for example, extending the current agreement by a few months or dropping certain services) gives you leverage. By scripting these elements in a playbook, your team can negotiate assertively and consistently, without scrambling for decisions under pressure.
- ✅ Evaluation of Alternatives: One often overlooked aspect of renewal preparation is evaluating alternatives to simply signing the same EA again. Consider what alternatives make sense for your organization, as this can both provide leverage in negotiations and potentially be a viable path if negotiations falter. Alternatives can take several forms. Alternative licensing programs: If your organization’s size or needs have changed, explore whether a Microsoft Customer Agreement (MCA) or Cloud Solution Provider (CSP) arrangement would be more cost-effective or flexible than an EA. Microsoft itself might suggest moving to CSP if your seat count is below a certain threshold. Understand the pros and cons – CSP can offer monthly flexibility, but might have higher unit prices; an EA offers fixed pricing but with less flexibility. Alternative vendors or solutions: In areas where Microsoft’s proposal is too costly or doesn’t align with your strategy, are there other options? For instance, some companies might consider shifting certain users to Google Workspace or AWS for specific workloads if Microsoft’s terms are unfavorable (even if only as a negotiating tactic). Or perhaps using third-party security or telephony solutions instead of Microsoft’s add-ons if those come at a premium. The goal isn’t necessarily to replace Microsoft, but to have a plan B in mind. By conducting this evaluation, you can approach the renewal with confidence, knowing that you have choices. This mindset prevents you from feeling trapped into accepting a bad deal. Moreover, when Microsoft knows you are informed about alternatives (and willing to consider them), you are likely to get a more competitive offer to keep your business.
(Use the above checklist as a guiding template. You can customize it by adding any organization-specific items, but these core areas cover the essentials of EA renewal readiness.)
How to Use the Checklist
Having the checklist is only useful if you apply it at the right times.
Here’s how to incorporate it into your renewal planning process:
- 3–6 Months Before Renewal: Begin working through the checklist items methodically. At around the 6-month mark (or earlier for very large enterprises), kick off the renewal project. Begin with internal data gathering: complete the current usage analysis and internal audits first, as these tasks can take time. Around 6 to 3 months out, focus on forecasting needs and aligning with executives on objectives – this is when you solidify your strategy. Regularly meet with your renewal team to review progress on each checklist item. By 3 months before expiration, you ideally have your internal house in order (usage data, future requirements, compliance status, and a negotiation plan drafted).
- 1 Month Before Renewal: In the final month leading up to the renewal date, use the checklist as a final review to ensure nothing has been missed. By this point, you are likely in active talks with Microsoft. Double-check items like having all executive approvals in place for the negotiated terms, confirming that all internal stakeholders are updated on negotiation status, and verifying that any last-minute Microsoft proposals have been evaluated against your checklist criteria (for example, if Microsoft throws in a new offer, does it align with your objectives and have you considered its impact?). This is also the time to ensure the team has prepared any necessary documentation (such as a final license inventory, a summary of agreed changes, or a brief for senior management). Essentially, the last month’s use of the checklist is about validation – making sure your preparation translates into execution without loose ends. If any checkbox remains unchecked at this stage, address it immediately before signing day.
- During Negotiations: Bring the checklist and your notes from it to the negotiation meetings. It serves as a reference to keep you on track. During live negotiations or calls, it’s easy to get sidetracked by unexpected issues or concessions being discussed. The checklist helps you remember your pre-defined priorities and boundaries. For example, if a discussion veers into a new product Microsoft wants to bundle, you can recall that you evaluated alternatives and know whether you actually need it. Use the checklist items like a pilot’s pre-flight list – even as talks progress, periodically glance at it or have a team member quietly check that you’ve covered all critical points. Have you presented your usage analysis facts to counter any overestimation? Have you asked about any mystery line items in the quote? Did you revisit the topic of price protections or flexible terms, which was on your list? Negotiations can be stressful, but with a checklist in hand, you’ll be less likely to forget to bring up something important or to inadvertently agree to something outside your plan. After each negotiation session, update the checklist status by marking off items that have been settled or require follow-up. This running log will track your progress and highlight any remaining issues to be resolved in the next round. By the final agreement, you should see every item checked off as addressed.
Why a Renewal Readiness Checklist Matters
Using a renewal readiness checklist might sound like extra work, but it delivers significant benefits that far outweigh the effort.
Here are the key advantages:
- Better Leverage in Negotiations: Preparation equals power. By doing your homework (usage data, benchmarks, defined goals), you gain leverage to push back on Microsoft’s initial offers. You can counter proposals with facts and confidently ask for better terms. Microsoft’s sales team will realize you’re an informed customer with a plan, which means they’ll be more inclined to make concessions to win your business. Leverage can translate into better discounts, more favorable contract terms, or added value that unprepared buyers would miss out on.
- Fewer Oversights and Surprises: An EA renewal involves many moving parts, including technical requirements, financial calculations, and legal terms. A checklist approach ensures you don’t overlook critical components. It acts as a safety net, ensuring that necessary actions, such as a license true-up, a notice to cancel an unused service, or a required internal approval, don’t slip through unnoticed. Fewer oversights mean fewer last-minute scrambles and no “I wish we had thought of that earlier” regrets. It also helps avoid surprises from Microsoft – since you proactively covered compliance and contract reviews, you won’t be caught off guard by an unexpected audit claim or an obscure contract clause.
- Internal Alignment: Completing the checklist fosters alignment among IT, finance, procurement, and executive leadership. Everyone gets visibility into the plan and their role in it. This unity is crucial because it prevents internal disagreements during negotiations (for example, procurement and IT having conflicting priorities). With a checklist, the CIO, CFO, and other leaders have already signed off on key decisions as tasks were completed. Internal alignment means your team speaks with one voice to Microsoft, speeding up decision-making and ensuring support from all levels of the organization for the outcome.
- Cost Savings and Optimization: Ultimately, the checklist is a tool to drive cost efficiency and value. By identifying unused licenses and right-sizing your needs, you avoid paying for software you don’t use. By negotiating methodically using your playbook, you secure better pricing on the software you do need. Many organizations find that this structured approach yields significant savings – often cutting millions off a multi-year EA – or enables them to add important new services within the same budget. Beyond hard savings, you also achieve a more optimized license estate (no bloated entitlements, fewer redundant products), which can improve IT management in the future. In short, the checklist helps ensure every dollar spent on the renewal is intentional and justified.
5 Actionable Next Steps
If your Microsoft EA renewal is on the horizon, here are five practical steps you can take right now to kickstart the process:
- Mark Your Calendar and Set a Timeline: Identify the exact end date of your current Microsoft EA and count backwards to today. Establish a renewal planning timeline with key milestones (e.g., when to finish the usage audit, when to finalize requirements, when to start negotiations). This will give your team clear deadlines. If you have less than 6 months left, plan to compress and prioritize tasks accordingly.
- Assemble Your Renewal Team: Pull together a cross-functional team for the EA renewal project. Include IT asset managers or software licensing specialists, procurement or sourcing managers, finance representatives, and an executive sponsor (like the CIO or IT Director). Kick off the project with a meeting to ensure everyone understands the checklist and their respective responsibilities for each item. Early team formation ensures you have the right expertise and authority behind the renewal effort from day one.
- Launch a License Usage Audit Now: Don’t wait – start gathering your current license and usage data immediately. Inventory all Microsoft products your organization uses, and collect usage statistics (e.g., active users for each service, current Azure consumption, etc.). Identify obvious areas of inefficiency (like unused licenses). This audit can take time, especially in large organizations, so beginning now will give you a head start. Aim to have a draft of your current usage analysis within the next few weeks.
- Define Future Needs and Budget Parameters: Initiate discussions with business unit leaders and IT architects to determine their requirements for the next 1-3 years from Microsoft. Will some new projects or expansions require additional licenses or upgrades? Simultaneously, work with finance to set preliminary budget expectations for the renewal (for instance, determine if maintaining flat spend is a must or if a certain percentage increase is acceptable for new capabilities). Document these future requirements and budget guidelines to ensure accurate planning. This will form the basis of your negotiation goals. It’s never too early to sketch out what success looks like – doing it now gives you a clear target to work towards.
- Download the EA Renewal Checklist PDF and Get Started: Access the Microsoft EA Renewal Readiness Checklist (PDF) provided with this article and save it to your workspace. Share it with all members of your renewal team. Start ticking off the first few items, such as the usage audit and team alignment tasks. Use it as a living document – update it regularly as you make progress. By downloading and actively using the checklist, you ensure that your preparation stays organized and on track. Consider scheduling a weekly or bi-weekly check-in meeting where the team reviews the checklist status and plans the next actions. This way, momentum builds immediately, and everyone stays accountable to the renewal timeline.
By taking these steps now, you’ll lay a strong foundation for a smooth and successful Microsoft EA renewal. The key is to start early, stay organized with the checklist, and involve the right people.
With preparation underway, you can approach the upcoming renewal with confidence and control, rather than feeling rushed and uncertain.
Good luck with your EA renewal – and remember that a little preparation today can save you a lot of cost and hassle tomorrow.
Read about our Microsoft EA Negotiation Service.
Microsoft EA Negotiation Templates & Playbooks: How to Stay in Control
