6 Months Until Microsoft EA Renewal: Key Mid-Stage Milestones

6 Months Until Microsoft EA Renewal

Introduction – Why the 6-Month Mark is Critical

At six months before your Microsoft Enterprise Agreement (EA) renewal, you enter the mid-game of the EA renewal timeline.

This is the stage where careful planning shifts into execution. Microsoft’s sales team is likely expecting signals about your renewal intentions at this point, but a savvy negotiator uses this time to solidify their own strategy first.

By being fully prepared at the six-month mark, you maintain leverage and control – rather than succumbing to vendor-driven urgency. Read our ultimate guide to Microsoft EA renewal strategies.

In short, the groundwork you lay now will directly shape the outcomes of final negotiations in the coming months.

Being mid-stage in the renewal process means you still have time to maneuver, yet the countdown is real.

It’s a critical window to lock in your requirements, coordinate internal stakeholders, and quietly let Microsoft know you’re not an easy target for last-minute pressure.

This practical guide (written in the voice of a licensing negotiation expert) breaks down the key milestones and actions CIOs, procurement heads, and IT licensing managers should tackle six months before an EA renewal.

Each step focuses on preparation, cost control, and building negotiation leverage – so you can approach Microsoft on your terms with confidence.

Finalize Requirements

By six months out, you should have a detailed requirements document ready – essentially your playbook for the renewal.

This document clearly defines what you plan to buy (and not buy), the deal you’re aiming for, and any terms you want to improve. Finalizing your requirements now ensures internal alignment and prevents Microsoft from dictating the agenda.

Key elements to cover include:

• License Inventory & Needs: Document the exact quantities of each license or subscription you’ll need going forward. Base this on a thorough usage audit – drop any “shelfware” (unused licenses) and right-size your counts to actual demand. If you found that 200 Office 365 accounts were inactive, for example, plan to remove or reassign those so they don’t roll into the new agreement. Likewise, note any new products or services you intend to add (e.g., if you plan to adopt a Dynamics 365 module or more Azure services). This way, your renewal will cover only what’s necessary for the next term.
• Future Growth & Changes: Incorporate business growth plans and upcoming projects into your requirements. If you expect to hire 500 employees next year or expand into new regions, factor that into license counts. Similarly, account for planned tech initiatives – for example, if migrating some on-premises servers to Azure or rolling out a new Power Platform app, include those needs. Identifying products to remove or replace is equally important (maybe you’re dropping a legacy system or moving some users to a cheaper license tier). By aligning the EA with your 3-year roadmap, you avoid over-buying or under-buying. In short, ensure the renewal bundle fits your organization’s trajectory, not just the status quo.
• Target Pricing and Discounts: Set clear cost goals for the renewal. What would a “good deal” look like for your organization? This might be a target discount percentage off Microsoft’s price list or a not-to-exceed budget number approved by finance. For instance, you might aim to reduce the total three-year spend by 10% compared to the last EA, or expect at least a 15% discount on certain high-value licenses based on industry benchmarks. Defining these targets now gives you a yardstick to judge Microsoft’s offers later. It also ensures procurement and finance are aligned on the financial expectations – no surprises when a proposal comes in. If your CFO is counting on flat spend (0% increase) and Microsoft’s first quote is +15%, you’ll know it’s not acceptable. Locking in a budget guardrail and discount goal at this stage strengthens your negotiating position.
• Must-Have Contract Terms: Identify any contractual improvements or protections you want to negotiate. Mid-stage is the time to pin down these “ask list” items so you can build them into your strategy. Examples might include: tighter audit clauses (to limit surprise audits), more flexible true-up/down terms (e.g., the right to reduce license counts annually if usage drops), price increase caps (multi-year price protection), or an early termination option for specific services. Perhaps you want to improve payment terms or add an exit clause for new cloud services. Prioritize the terms that matter most to your business. By listing these now, you won’t forget them in the heat of negotiations, and you can ensure your team speaks with one voice on non-negotiables.
• Internal Alignment and Approval: Before engaging Microsoft on specifics, ensure all key stakeholders internally have reviewed and approved this requirements document. This means IT, procurement, finance, and any business unit leaders impacted agree on the plan. Achieving consensus now is crucial – Microsoft’s reps are skilled at exploiting any internal discord or lack of clarity. If everyone from the CIO to the IT asset manager understands the approved requirements, budget, and terms, Microsoft will get a unified message. No division-by-division wish lists, no end-runs around procurement. Take this time to brief your executive sponsors (CIO, CFO, etc.) so they fully back the strategy. A unified front not only prevents internal confusion, it also boosts your credibility in Microsoft’s eyes – they’ll realize you’re organized, serious, and not an account that can be easily split and conquered.

What to do 12 months out, 12 Months Ahead: Early Planning Checklist for Your Microsoft EA Renewal

Initial Microsoft Discussion

Around the six-month mark, it’s time to formally engage Microsoft or your Licensing Solution Provider (LSP) in preliminary renewal conversations.

The key here is to initiate contact on your own terms – you want to project confidence and preparedness, not panic. Early engagement signals to Microsoft that you’re actively managing the renewal (and not just going to blindly sign whatever is offered).

Here’s how to handle these initial discussions strategically:

• Set the Tone: Reach out to your Microsoft account manager or partner rep and schedule a kickoff discussion about the upcoming renewal. Communicate a few high-level priorities from your side. For example, you might say your organization is “focused on cost optimization and evaluating all options this cycle.” Mention broad goals like “reducing overall spend” or “ensuring we only pay for what we use.” This sets a tone that you’re looking for a lean, value-focused deal. You can also subtly indicate you’re exploring alternatives (e.g., other licensing models or providers) without going into detail. The idea is to let Microsoft know you’re prepared and have choices, which encourages them to take your account seriously.
• Listen and Learn: In this first conversation, do more listening than talking. Microsoft will often use early meetings to float their agenda – perhaps hinting at new products they want to upsell or gauging your interest in certain bundles. Take note of Microsoft’s positioning and any “hints” they drop. Are they pushing everyone to upgrade to Microsoft 365 E5? Are they excited about you adopting the latest Copilot AI add-on or a big Azure commitment? Pay attention, as these clues reveal where Microsoft sees revenue opportunities. Also listen for any subtle urgency (“We should get this done by the end of the quarter to secure discounts”) – this is classic vendor-driven pressure. Logging these insights now will help you prepare counter-arguments and prioritize your asks later. Just as important: ask open-ended questions. For instance, “Are there any upcoming promotions or licensing changes we should know about as we plan?” This can prompt your rep to share useful intel (maybe a new licensing program or discount that’s on the horizon).
• Stay Non-Commital: While you want to be cooperative and professional in early talks, guard your information carefully. Do not reveal your budget, your specific internal timelines, or how badly you “need” a deal. Avoid any phrasing that implies urgency or dependency (e.g., don’t say “We’re really hoping to renew quickly to avoid issues” – that signals you’re desperate). Instead, project a calm confidence: “We’re assessing our needs and options; we’ll be in touch with specifics when we’re ready.” By not rushing and not laying all your cards out, you maintain leverage. Microsoft will realize you are not an easy mark for a quick renewal; they’ll have to earn it. Early in the process, it’s perfectly fine to be a bit vague and play your strategy close to the vest. The goal of the initial discussion is simply to open lines of communication, gather Microsoft’s initial stance, and let them know you’re an informed customer with a plan. Once they sense you are organized and potentially considering alternatives, they’ll be more likely to bring competitive offers to keep your business.
• Document the Conversation: After any call or meeting, circulate a quick internal summary. Note what Microsoft seemed to emphasize and any offers or timelines they mentioned. This record will be useful as you refine your negotiation strategy. It also helps ensure your whole team has consistent information. If Microsoft’s rep mentioned, say, “Discounts might expire by June 30,” you’ll all know to treat that with healthy skepticism (and to possibly leverage the timing to your advantage). Essentially, use the initial engagement to gather intel and set the stage, but commit to nothing. By driving the first contact proactively and professionally, you assert control over the renewal narrative from the get-go.

Read what to do 3 months out, 3 Months Until EA Renewal: Final Preparation Steps

RFP or Competitive Bids (If Applicable)

Six months before renewal is an excellent time to introduce competition into the mix – if your organization’s policies allow it. Microsoft would love to assume you’ll simply renew through the same channel without shopping around, so prove them wrong.

Running a parallel RFP (Request for Proposal) or seeking competitive quotes now can significantly strengthen your hand in negotiations.

Here’s how to leverage this step:

• Explore Alternative Resellers or Channels: If you work with a Microsoft LSP or reseller, consider soliciting bids from a couple of competing LSPs for the same set of products. Likewise, you could ask for pricing on alternatives like a Cloud Solution Provider (CSP) program or Microsoft’s newer MCA (Microsoft Customer Agreement) model, if those are feasible options. The goal is to get concrete numbers from other sources to compare against Microsoft’s direct renewal pricing. Even if you fully expect to stay with Microsoft’s EA, having another quote or two in hand arms you with benchmark pricing. It shows what the market offers and prevents complacency from your incumbent provider.
• Create Pressure through Options: A well-timed RFP signals to Microsoft and your current reseller that they are not the only game in town. Vendors tend to sharpen their pencils when they know a competitor is lurking. If Microsoft believes you might move some business to another channel (or another vendor altogether), they are more likely to concede on price and terms. For example, if a competing reseller offers a better discount on the same licenses, you can use that to ask Microsoft to match or beat it. And if you get a quote for shifting some licenses to CSP on a monthly model, Microsoft might counter with more flexibility in the EA to dissuade that move. The mere act of showing competition puts you in a stronger negotiating position.
• Benchmark Value, Even If You Don’t Switch: You may ultimately decide not to change providers or licensing models due to practical reasons. That’s okay – the information gained is still invaluable. External quotes give you an objective point of reference. For instance, if Reseller B offers your Office 365 E5 renewal at 12% off the list price and your current reseller (or Microsoft direct) is only offering 5%, you have hard evidence that 5% is not the best you can do. You can then press them to improve. Think of competitive bids as insurance against overpaying: they ensure you’re not operating in a vacuum. In negotiations, you can subtly mention that you’ve done your homework and are aware of better pricing out there – without necessarily revealing sources. That often is enough for Microsoft to reconsider its first offer.
• Mind Your Procurement Rules: Before launching an RFP or engaging multiple bidders, ensure you follow your organization’s procurement guidelines. In some cases, you might be required to bid out large contracts anyway. In others, you may have a preferred reseller partnership – but even then, nothing stops you from “benchmarking” quietly. Also, be transparent with any internal stakeholders who need to approve this process. The last thing you want is to stir up vendor drama without the backing of leadership. If done properly, however, a competitive sourcing exercise at 6 months out can save money and reveal negotiation angles you hadn’t considered. Even if you don’t switch suppliers, you’ll walk into renewal talks with Microsoft equipped with facts and alternatives – which is exactly where you want to be.

True-Up and Cleanup

Mid-stage in the renewal cycle is also a time for cleanup. To set a solid foundation for negotiations, you’ll want to true up, clean up, and tighten up your licensing footprint.

In simple terms, ensure all your licensing records are accurate and that you aren’t carrying any dead weight in your EA.

Here are the steps to execute:

• Perform Any Due True-Ups Now: If your EA requires an annual true-up (adding licenses for any over-usage in the past year), the six-month mark is a good time to handle it if you haven’t already. Make sure you account for any new users or extra deployments that occurred since your last report. It may feel odd to purchase licenses right before renewal, but doing so proactively neutralizes a potential Microsoft pressure point. You don’t want to be in a formal negotiation and have Microsoft point out you’re out of compliance on SQL Servers or Office 365 accounts – that gives them leverage to force a quick sale. By trueing up now, you resolve compliance gaps on your terms and budget for those costs calmly, rather than in a panic later. It’s like cleaning up your score before going into a test – no loose ends for Microsoft to exploit.
• Deactivate and Reclaim Unused Licenses: License cleanup is arguably the easiest money-saver in a renewal. By six months out, comb through all user accounts, subscriptions, and installations tied to your EA. Deactivate any dormant accounts (for example, employees who left or duplicate test accounts) and remove their licenses. Reclaim unused installations – maybe certain software was installed for a project that ended, or extra Visual Studio subscriptions that nobody is using. Every license you can eliminate now is one less license you pay for in the renewal. If you find 100 unused Office 365 E3 licenses, that’s a direct reduction of 100 in your renewal count, which could be significant dollars saved. This cleanup ensures your renewal baseline (the quantity of each product you’ll carry forward) is as lean as possible. Microsoft, of course, would love you to renew everything as-is (including the shelfware), but your job is to only renew what drives value.
• Optimize Active Usage: In addition to removing truly unused licenses, scrutinize under-utilization. Perhaps you have 500 users on a premium SKU (say Microsoft 365 E5), but only 100 are actually leveraging the advanced features – the rest could be just as productive on an E3 license. Identify these opportunities and plan to downgrade or reallocate licenses at renewal. This might mean splitting your EA to a mix of editions (e.g., fewer E5s, more E3s). The six-month point is ideal for confirming these decisions and even testing their impact (perhaps by piloting an E5-to-E3 downgrade for a subset to ensure no disruption). By rightsizing license levels to match usage, you cut out wasteful spending. Plus, this sends Microsoft a message that you won’t pay for overkill features, which may nudge them to offer a better deal to keep those premium seats at all.
• Validate Your Data: As you true-up and clean up, double-check every count and report. Ensure that your internal records match Microsoft’s view of your entitlements and usage. Reconcile things like Active Directory user counts vs. licenses assigned, or Azure consumption vs. Azure precommitments. The goal is to eliminate any surprises. If there are discrepancies, figure them out now; don’t wait for Microsoft to point them out later. Also, document the final numbers and the actions taken (e.g., “decommissioned X servers, freed up Y licenses”). This validation gives you confidence when negotiations begin. You can firmly push back on any attempt by Microsoft to inflate your needs because you have the data to prove your actual usage. In short, cleaning house now means you enter talks with a tidy, accurate licensing environment – the best starting point for arguing you should pay less, not more.

Draft Negotiation Strategy

With requirements finalized and your environment optimized, it’s time to map out your negotiation strategy. Think of this as your internal game plan for the give-and-take with Microsoft in the coming months.

Drafting your strategy at the six-month mark ensures your team is ready long before formal negotiations start (typically around 3 months out).

A solid negotiation playbook will make Microsoft’s famed sales tactics much less effective against you.

Key components of your strategy include:

• “If/Then” Scenario Planning: Anticipate Microsoft’s moves and decide your counter-moves in advance. Sit down with your core team and brainstorm the likely proposals or pressures Microsoft will bring, then script your responses. For example, if Microsoft’s first offer is only a 5% discount off the list, then you’ll counter by asking for 15%, to meet somewhere around 10%. Or, if Microsoft pushes an upsell – say they insist you add the new Copilot AI add-on for all users – then you’ll request an equivalent concession (perhaps deeper discounts on security packages or additional Azure credits) to offset that cost. Likewise, suppose Microsoft’s contract stance is a rigid 3-year term with no flexibility. In that case, you plan to negotiate an opt-out clause or the ability to adjust down during the term for greater agility. By mapping these scenarios now, you won’t be caught flat-footed later. It’s essentially practicing your plays so you execute smoothly when the pressure is on. Below is an example of how some if/then scenarios might look:

• Assign Roles and Responsibilities: Effective negotiation with Microsoft often requires a team to play multiple angles. Now is the time to decide who will do what when talks heat up. For instance, assign a lead negotiator (often the procurement or sourcing manager) who will handle pricing discussions and be the primary voice to Microsoft. Designate an IT licensing specialist to cover product-specific questions and usage data during meetings (so Microsoft hears from an expert if they claim you “need” more of something). Have someone from finance ready to validate budget impacts of various proposals, and a legal advisor to scrutinize contract terms language. It’s also wise to decide which executive will step in if escalation is needed – perhaps your CIO will join a late-stage call to apply pressure for a better discount, or the CFO will be looped in to convey that the deal still doesn’t meet financial requirements. By planning roles, you ensure each aspect (pricing, technical, legal, executive clout) is covered by the right person at the right time. Microsoft’s team will certainly include sales, technical specialists, and managers; you should mirror that depth on your side to match them point-for-point.
• Plan the Cadence and Escalation Path: Lay out a rough timeline for the negotiation process post-6 months. This might include scheduling internal prep meetings (e.g. a weekly sync among your team to update on Microsoft’s communications) and tentatively planning when formal proposals will be exchanged. Decide early how you will handle escalation if talks stall or if Microsoft isn’t budging on key issues. For example, you might plan that if no satisfactory discount is reached by 2 months out, you’ll involve a higher-up at Microsoft or have your CEO send a note to their executive. Or, if certain contract terms can’t be agreed on, you’ll bring in your legal counsel to negotiate directly with Microsoft’s legal. Having an escalation plan keeps the negotiation moving and signals to Microsoft that you’re ready to push things up the chain if needed. It also prevents internal panic – your team knows exactly what steps to take as the clock ticks down.
• Outline Your Walk-Away and BATNA: While the actual “walk-away” decision (not renewing by the deadline) is something to firm up closer to 0–3 months out, you should start drafting those contingency plans now. BATNA (Best Alternative to a Negotiated Agreement) essentially means what’s your backup if you don’t reach a deal in time. At six months, sketch out the basics: could you extend the current agreement briefly? Could you temporarily shift to monthly subscriptions (via CSP) to buy more time? Identifying these options now is important because it informs your negotiation style – a negotiator with a credible backup won’t concede as easily. Let your executives know that you are preparing fallbacks (even if you hope not to use them), such as a month-to-month plan or splitting some services off to other vendors. When Microsoft sees that you aren’t afraid to delay or take an alternative route, they’re far less likely to play hardball on “this deal must be signed or else” tactics. At this stage, you don’t have to finalize the walk-away plan, but having a draft in your strategy means you’re mentally prepared to use it if necessary.

Drafting your negotiation strategy in advance gives your team confidence and a unified approach to negotiations. It turns the upcoming renewal discussions into a series of planned responses rather than ad-hoc reactions.

By the time you’re three months out, this strategy will be your guidebook as you enter formal negotiations. Remember, discipline and preparation now will prevent mistakes when Microsoft turns up the heat later.

Rough Pricing Benchmark

Now is also the moment to pin down your pricing benchmarks – a clear sense of what a fair and competitive deal looks like.

Walking into negotiations without a benchmark is like going into a market with no idea of prices; you’d have no clue if you’re being overcharged.

At six months out, do the homework to gather benchmarks so you can evaluate Microsoft’s offers critically:

• Research Industry Norms: Check any available data on typical discount levels or pricing for Microsoft EAs similar to yours. This might involve talking to peer companies (if you’re in networking groups where people share licensing experiences) or engaging a licensing advisor who has anonymized benchmark data. For example, you might learn that enterprises of your size usually get 20% off certain Office 365 SKUs, or that a company with similar Azure spend secured a significant credit or discount. Knowing these ballpark figures gives you a realistic target. It guards against both low expectations (so you don’t settle for a 5% discount if others get 15%) and overly high hopes (so you don’t hold out for a 30% cut if nobody ever gets that in your segment).
• Use Your Own History & Alternatives: Your current EA pricing is a natural benchmark, too. Analyze how your pricing today compares to Microsoft’s list prices; that effectively was your last discount. Ideally, you’re aiming to improve upon it or at least not lose ground. Also factor in any quotes from the competitive bid process (if you did one). For instance, if an alternate reseller offered a certain bundle at $X, that price becomes a reference point – even if you stick with Microsoft direct, you know $X is attainable in the market. Additionally, consider the cost of going to cloud subscriptions month-to-month (the CSP model). That can serve as a “ceiling” benchmark; if Microsoft’s renewal proposal somehow makes the EA more expensive than simply buying monthly licenses, something is very wrong! With these data points, you essentially frame the high and low bounds of what you should pay.
• Internalize the Benchmark (Share with Stakeholders): Make sure your internal team, especially executives who might approve the deal, understands these benchmark expectations. Before Microsoft ever presents a formal quote, brief your CIO/CFO on what you believe a good deal comprises. For example, “Based on our analysis, a reasonable total cost for this renewal is around $Y over 3 years, which equates to roughly a Z% discount. Anything above that, we consider high.” This preps them to not freak out if Microsoft’s first number is huge (they’ll know it’s part of the dance), and conversely, they won’t mistakenly think an okay-ish offer is “great” if it’s actually below average. When everyone knows the benchmark, you can judge offers quickly and consistently. It’s much easier to push back on Microsoft when you have data: “We’ve done our homework, and this price is above market by our estimates.” It lends credibility to your asks for a better deal.
• Evaluate Microsoft’s Quotes Against the Benchmark: Although formal proposals might come closer to 3 months out, Microsoft could float some preliminary figures earlier. Whenever you start seeing numbers, measure them against your benchmark. If they’re in range or better – good, you know you’re on track (though you still might push for more). If they’re worse, you have justification to reject and counter. Keep your benchmark document handy as a checklist during negotiations. It will help you stay objective and not get swayed by sales tactics like “this is the best we can do” or “others are paying more.” If your intel says otherwise, trust it. Overall, having a grounded pricing benchmark by the six-month mark means you enter the serious negotiation phase armed with knowledge. In the game of buying, knowledge truly is power.

Checklist – 6-Month Milestones

At the mid-stage of your EA renewal process, make sure you can tick off the following key actions.

This checklist summarizes the critical steps to have completed (or well underway) six months before your Microsoft EA expires:

• Requirements document finalized and approved.
  A comprehensive internal document of what you need (licenses and terms), reviewed and blessed by IT, procurement, finance, and key executives.
• First engagement with Microsoft/LSP completed.
  Initial high-level discussion held with your Microsoft rep or reseller, signaling you are preparing and gathering information (without committing to anything yet).
• Competitive bids or RFP process started (if applicable).
  Alternate quotes from other resellers or licensing programs requested, to benchmark pricing and keep Microsoft on its toes.
• True-up executed and cleanup performed.
  All usage reconciled – any additional licenses required have been procured, and all unused or unneeded licenses identified to drop at renewal. Environment and records are tidy and accurate.
• Draft negotiation strategy documented.
  Internal negotiation playbook created, including scenario plans (if/then counters), team roles assigned, meeting cadence set, and escalation paths defined. Everyone on the team knows the game plan.
• Pricing benchmark gathered and validated.
  Market pricing intelligence collected (from peers, consultants, past deals, or competitive quotes). Clear benchmarks for “good deal” vs “bad deal” established and agreed upon internally.

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