Maximizing Value from Microsoft Software Assurance (SA)

Maximizing Value from Microsoft Software Assurance
Guidance for CIOs and Sourcing Leaders in Large Enterprises

Software Assurance (SA) is Microsoft’s maintenance and benefits program, which is attached to volume licenses. For large enterprises, SA represents a substantial annual investment–roughly 25–30% of the license cost per year–in exchange for a bundle of upgrade rights, support, and other value-added benefits.

To justify this spend, CIOs and sourcing leaders must ensure their organizations fully leverage SA across data centre products (like Windows Server, SQL Server) and desktop products (like Windows OS, Office). An SA strategy can yield significant cost savings, smoother technology upgrades, and improved operational efficiency.

Done poorly, SA can become an expensive line item with underutilized benefits. The following sections detail what to do, what to consider, the practical impacts, and clear recommendations to maximize returns on Software Assurance.

Things to Do

Organizations should take a proactive, structured approach to extract full value from Software Assurance.

Below are specific actions and strategies to implement:

• Inventory Your SA Benefits and Usage: Begin with a comprehensive audit of your organization’s SA entitlements. Many SA benefits are not automatically delivered – you must know about them and activate or use them. Catalogue benefits across desktop and server licenses (e.g. Windows, Office, SQL Server, etc.), including upgrade rights, support incidents/credits, training programs, planning services (or their modern replacements), cloud use rights, disaster recovery rights, and other perks. Identify which benefits have gone unused in the past. For example, check if your team ever redeemed available training vouchers or if you utilized the Home Use Program (now called the Workplace Discount Program) that offers employees discounted Office 365 subscriptions. This inventory provides a baseline and highlights value that might be “left on the table.” Assign an owner (or team) to each significant benefit to ensure accountability for using it.
• Plan to Use Benefits Before They Expire: Many SA benefits come with use-it-or-lose-it time frames tied to your agreement term. Create a schedule or roadmap for utilizing them within the active period. For instance, if you still have Software Assurance Training Vouchers (from before their retirement) or other training credits, schedule employee training sessions before those vouchers expire. Similarly, if you had Planning Services days banked (which Microsoft has retired as a formal program), ensure you engage those services via Microsoft partners or the newer alternatives as soon as possible. (Microsoft has transitioned Deployment Planning Services into its FastTrack program – eligible customers should use FastTrack’s planning and deployment assistance for cloud projects instead of the old SA Planning Services days.) By timing these activities within your SA term, you avoid losing benefits you’ve effectively paid for. A benefit utilization plan can also stagger different activities (upgrades, training, deployment workshops) so your organization isn’t trying to use everything at once near the end of the agreement.
• Track Renewal Dates and Align with IT Roadmaps: SA is typically purchased in multi-year blocks (often via a three-year Enterprise Agreement). Proactively track when your SA term is up for renewal. Begin internal discussions 12–18 months before renewal to decide what to continue, add, or drop. Align these decisions with your technology roadmap. For example, if a major software upgrade (say, a new Windows Server or SQL Server release) is expected right after your SA expires, it might be wise to renew your SA to cover that upgrade. Conversely, if you plan to decommission a legacy system or move entirely to SaaS/cloud alternatives, you might opt not to renew SA on those retiring products. By syncing renewals with your business and IT strategy, you can avoid paying SA on assets that won’t be used and ensure coverage where it’s truly needed. Early planning also gives you time to negotiate with Microsoft or explore alternate licensing (such as subscriptions) at renewal rather than rushing into a renewal without analysis.
• Align SA Benefits with Cloud Strategy: Use SA to bridge into the cloud smartly. Many SA benefits are specifically designed to support cloud and hybrid scenarios – take advantage of them. For instance, Azure Hybrid Benefit (AHB) allows you to use existing Windows Server and SQL Server licenses with active SA on Azure, significantly reducing Azure VM costs (in fact, this can save around 30–40% on Azure infrastructure costs). If migrating workloads to Azure, leverage AHB for each eligible instance rather than paying full price for cloud licenses. Likewise, SA’s License Mobility rights let you bring certain server application licenses (e.g., SQL Server, Exchange, SharePoint) to run on qualified cloud or hosting providers. Use this to deploy on Amazon Web Services or other clouds without double-paying for licenses, but ensure the provider is authorized under Microsoft’s rules. (Note: Microsoft’s rules evolved in 2019-2022, limiting license mobility on certain large third-party clouds for new licenses. Check current policy and use legacy entitlements if applicable.) Integrating SA’s cloud-use rights into your cloud migration plan is key. This alignment can drastically lower costs during transitions. Additionally, SA often allows dual-use rights during migrations. For example, you can use an on-premises server for 180 days while establishing the same workload in Azure without extra licensing. Such provisions smooth out the move to the cloud. Ensure Your
  Cloud architecture and licensing teams work together so that every eligible on-prem license with SA is factored into cloud deployment planning.
• Upgrade Proactively to New Versions: One of SA’s fundamental benefits is New Version Rights – the entitlement to upgrade to the latest software releases you own. Take full advantage of this. Don’t let inertia keep your organization on outdated versions. Develop an upgrade cadence aligned with Microsoft’s release schedule and your internal testing/validation cycles. This might mean moving to Windows 11 Enterprise (from Windows 10) or deploying the latest Office version organization-wide as part of your evergreen IT strategy for desktop software like Windows and Office. For data centre products, plan upgrades to Windows Server 2022 or the latest SQL Server as they become available under SA. Upgrading extracts the value you paid for (avoiding the need to purchase new licenses) and improves security and performance by keeping systems current. It can also reduce support costs – as older versions exit mainstream support, you’d otherwise pay for extended support or risk security exposure. By using SA to stay current, you maximize the return on your license investment and avoid big one-time costs for new licenses. Tip: Coordinate major upgrades with your SA renewal cycle – if a crucial upgrade won’t arrive until after your term, negotiate to extend or adjust accordingly.
• Leverage Additional SA Perks (Training, Support, and Tools): Ensure you exploit SA’s “softer” benefits that can boost your IT team’s capabilities and reduce other expenses. For example, Technical Training – while the classic Training Voucher program ended in 2022, Microsoft now provides free on-demand learning (via Microsoft Learn) and some instructor-led training discounts. Encourage your teams to use these resources as part of continuous learning (perhaps schedule hackathons or certify staff on new tech you’re entitled to train on under SA). Planning Services – as noted, the formal vouchers were retired, but Microsoft’s FastTrack service and partner-led workshops have taken their place for planning cloud deployments or upgrades. Schedule those engagements to get expert guidance without extra cost, instead of paying consultants separately. 24×7 Support – Microsoft adjusted SA’s support benefit recently (moving from a limited number of free support incidents to an “as-needed” support model for qualifying customers, plus credits toward Unified Support contracts). If your organization qualifies for any included support, ensure your support desk knows how to invoke it when critical issues arise. This can save tens of thousands of dollars in support fees. Even if full Microsoft Unified Support is needed, having SA might provide a cost offset – use that in your support contract negotiations. Other tools: if you have Windows Enterprise SA, deploy the Microsoft Desktop Optimization Pack (MDOP) tools (e.g. for virtualization application management) that come with it; if you have SA on SQL/Windows Server, utilize disaster recovery rights (such as the right to run passive secondary instances for failover without additional licenses – very useful for high availability setups). Each of these perks saves money (training or consulting you don’t have to purchase) or adds value to your IT operations (improved skills, better uptime, etc.). Make a checklist of all these benefits and ensure each has an owner and a plan for utilization during your agreement period.
• Use Step-Up Licenses and License Transition Options: Software Assurance often provides flexibility to upgrade or transition your licenses in ways that would be cheaper than buying brand-new licenses. One example is the Step-up license: if you own a lower edition (say, SQL Server Standard) with SA, you can pay just the price difference to convert it to a higher edition (SQL Server Enterprise) without purchasing a full new license. Use this to unlock higher-tier features cost-effectively when needed. Another scenario is transitioning to cloud subscriptions – historically, Microsoft offered discounted “From SA” subscription licenses (for instance, moving from Office with SA to Microsoft 365 subscriptions at a reduced rate). Check for any available transition SKUs or promotions when planning a move to the cloud. Note: Microsoft has recently signalled changes in these transition offers (e.g., phasing out some “From SA” discounts), so time your moves to take advantage of incentives while they exist. Avoid paying twice for similar functionality – use SA’s rights to smoothly shift your licensing model (on-premises to cloud, or Standard to Enterprise editions, etc.) with minimal financial waste.
• Engage Independent Licensing Expertise: Maximizing SA value isn’t always straightforward – the program rules and benefits have many nuances. Consider working with an independent licensing expert (for example, firms like Redress Compliance or similar specialists) to review your Software Assurance usage and plans. These advisors do not sell Microsoft licenses but focus on license optimization and compliance. An independent expert can help spot overlooked benefits (e.g. unused cloud use rights or secondary use rights), identify areas where you might be over-licensed or underutilizing SA, and assist in crafting a renewal strategy that serves your interests (not just the vendor’s quota). They can also objectively assess whether maintaining SA on certain products is cost-effective or if alternative licensing (such as dropping SA and later buying new licenses or shifting to subscriptions) would save money. Bringing in third-party expertise well before your renewal can equip you with data and negotiating points to get a better deal from Microsoft. In short, treat SA like any significant investment – get expert second opinions to ensure you’re not missing opportunities to get more value or to save costs.

What to Think About

When formulating your Software Assurance strategy, several strategic and financial considerations should be top of mind for CIOs and sourcing leaders:

• Cost-Benefit Analysis (ROI of SA): Continuously evaluate whether the annual cost of SA (≈25% of license cost for servers, 29% for desktop software, per year) is yielding proportional value. If you upgrade frequently (e.g. every 2–3 years to new versions), SA is likely paying off by avoiding large one-time upgrade purchases. If your upgrade cycle is slow (e.g., you stay on the same software version for 5+ years), you might be paying more into SA than you’d spend to simply buy a new version outright when needed. A roughly four-year upgrade horizon is often cited as the break-even point – beyond that, the financial benefit of SA diminishes. Think critically about your organization’s actual refresh cycle: are you on a rapid innovation path, or do you tend to skip versions? Use data (e.g. how many SA-covered upgrades did you actually deploy in the last cycle) to inform this analysis. Also, factor in the monetary value of other benefits used (training, support incidents) when weighing SA’s cost – those can tilt the equation if fully utilized. The goal is to ensure SA is a net positive investment; if it’s not, plan to adjust your approach (either leverage it more or consider scaling back coverage).
• Overlapping Entitlements (Avoid Paying Twice): Large enterprises often have complex Microsoft licensing footprints, including newer subscription-based products like Microsoft 365 (which bundles Windows 10/11 Enterprise, Office 365, EMS, etc.) alongside traditional on-prem licenses with SA. Be cautious of entitlement overlap. For example, suppose you’ve moved many users to Microsoft 365 E3/E5 subscriptions. In that case, those users already have rights to the latest Office apps and Windows Enterprise – continuing to maintain SA on separate Office or Windows licenses for them could be redundant. Similarly, Microsoft 365 includes client access license rights that might overlap with on-prem CALs you’re paying SA on. Analyze your license inventory in light of cloud subscriptions: Identify where SA benefits replicate what your subscription provides. Reducing SA coverage or the number of licenses at renewal may make sense if the functionality is now covered under a SaaS model. The same goes for cloud services: Office 365 provides continuous updates by default (making SA on old perpetual Office unnecessary for those users). Azure services might include certain support or DR capabilities that you otherwise paid for SA on-prem. Streamline your entitlements so you’re not double-covering the same user or system with a subscription and an SA-covered license unless there’s a clear need. This requires coordination between teams managing cloud subscriptions and those managing volume licenses – a unified view of all Microsoft spending to eliminate waste.
• Changes in SA Program Benefits: Recognize that Microsoft has been evolving the Software Assurance program over time, generally shifting away from some legacy benefits and pushing cloud-aligned services. For instance, in recent years, Microsoft retired popular SA benefits like Training Vouchers and Deployment Planning Services, replacing them with broader services (free online learning, FastTrack, etc.). They also changed support: the old model of a certain number of free support incidents through SA is gone, pivoting to credits toward Unified Support. These changes mean that the value proposition of SA today is different from what it was a few years ago. It’s important to stay updated on what you get with SA now (and what you don’t). Some benefits you might have counted on historically may no longer be offered – adjust your expectations and plans accordingly. Also, keep an eye on announcements: Microsoft can (and does) modify SA terms. For example, if, down the road, they decide to phase out additional benefits or alter usage rights, how would that impact your organization’s plans? Being aware of these shifts can influence how you approach renewals. You might choose shorter agreement terms or specific contract language if certain benefits are mission-critical to hedge against future program cuts. In summary, treat SA as a dynamic offering, not a static one – continuously recalibrate your strategy as the benefits mix changes.
• Impact of Cloud & Subscription Transition: Many enterprises are moving from on-premises software to cloud subscriptions (e.g., shifting from SQL Server on-prem to Azure SQL or Office on-prem to Office 365). This transition period is when SA decisions are especially critical. In the short term, SA can be extremely valuable in facilitating the move, using hybrid use benefits to save on cloud costs and ensuring you can upgrade to any new on-prem versions needed during migration. However, once you complete the migration, you may find that SA on legacy licenses is no longer needed (because you won’t use those licenses anymore). A key consideration is timing: you don’t want to prematurely drop SA if it provides value until you’re fully on the new platform, but you also don’t want to carry SA far beyond the value point. Microsoft has historically offered bridging discounts (like the “From SA” license transition offers) to help migrate customers into cloud services at a lower cost. Avail yourself of these when they make financial sense – they can reduce double-paying for cloud subscriptions while still under an EA. But note that as the cloud becomes the norm, Microsoft is tightening some of these deals (for example, as of 2024, new “From SA” discounted user subscriptions are being discontinued, signaling that Microsoft expects customers to shift outright). Thus, think about your long-term licensing trajectory. If your future is mostly cloud/subscription, strategize an exit from SA at the right moment (maybe by the next renewal cycle) and possibly negotiate migration bundles or credits. Conversely, if certain systems will remain on-prem for the foreseeable future (for technical or regulatory reasons), factor that into your SA renewal – those systems might justify ongoing SA to stay supported and updated while other parts of the portfolio go cloud. In essence, align your SA investments with the pace and scope of your cloud journey.
• Enterprise Agreement and Budget Considerations: In many large organizations, SA is baked into Enterprise Agreement (EA) enrollments – it provides the convenience of spreading payments annually and budgeting predictably for upgrades/support. From a financial management perspective, consider how SA fits into your IT budget strategy. The ability to spread out payments (rather than large lump-sum upgrades) is a cash-flow benefit of SA. However, it also becomes a fixed annual cost that needs to be justified each cycle. Work with your finance and procurement teams to model the next 3-5 years: Will SA help avoid big capital expenditures (by smoothing costs as operational expenses)? If so, that predictability might be valuable in itself. On the other hand, if budgets are tight and you foresee minimal usage of SA benefits, it might be time to trim those costs. Also, remember that Microsoft EA negotiations often allow some flexibility – you might negotiate credits, concessions, or alternative licensing mixes. For example, if you’re dropping SA on a product, you can convert some of those funds into a new cloud service in the same deal. Think holistically: sometimes, the best value comes from optimizing the overall EA package (licenses + SA + cloud subscriptions together) rather than looking at SA in isolation. And don’t forget the opportunity cost – money spent on SA for one product is unavailable for other initiatives. Ensure that continuing to invest in SA is among the best uses of that portion of your IT spending.
• Risk and Compliance Considerations: Deciding on SA also involves risk management. Ask: What is the risk of not having SA on a given product? For instance, if you choose to forgo SA on a critical database server, you risk being stuck on an old version or scrambling to fund an upgrade later if a security issue emerges. You might also lose license mobility and face limitations or higher costs if you move that workload to the cloud. There’s also compliance risk: if you don’t carefully plan and track your licensing when transitioning off SA, you could end up out of compliance (e.g., using a version you weren’t entitled to). Mitigate these risks by having a license lifecycle plan. If dropping SA, have a clear upgrade contingency plan (perhaps using savings to purchase an upgraded license later or having a support contract to bridge any gaps). If keeping SA, ensure you remain eligible for all benefits by maintaining continuous coverage (lapsed SA can’t usually be reinstated without buying new licenses). From a vendor management standpoint, consider the negotiation leverage aspect: having SA (or not) can influence your relationship with Microsoft. Sometimes, consolidating your spending (licenses + SA + cloud subscriptions) in one negotiation can give you more leverage for discounts. But if Microsoft perceives that you might drop SA, that could also motivate them to offer a better deal to retain your maintenance business. Use this as a strategic consideration – make Microsoft compete to demonstrate the value of SA to you, especially if you have options to go without it.

In summary, think strategically about Software Assurance: understand its cost structure, ensure other licenses don’t duplicate it, stay alert to program changes, align it with where your technology is headed, and weigh the financial and operational pros/cons carefully. SA should not be treated as an automatic renewal each cycle – it should earn its place in your IT strategy by providing tangible value aligned with your organization’s needs.

Practical Impact

How you manage Software Assurance can potentially impact your IT operations and financial outcomes.

Here are some practical scenarios illustrating the difference between fully optimizing SA and neglecting it:

If SA is actively managed and optimized:

• Maximized Return on Investment: Enterprises that diligently use their SA benefits effectively “reclaim” a lot of value. For example, a company that upgrades all its servers and desktops to the latest versions under SA doesn’t have to spend millions on new licenses for those versions. Suppose they use Azure Hybrid Benefit to move a workload to the cloud. In that case, they might save on Azure charges (e.g., one organization saved ~35% on their cloud VM costs by applying existing Windows Server licenses via SA rather than paying for Windows VM rates). They avoid consulting fees on migration projects by utilizing included planning services or FastTrack. In training, they upskill dozens of IT staff using what was provided in SA, saving perhaps hundreds of thousands in training budgets and ensuring better use of the software features they already own. These savings and cost avoidances mean the money paid into SA generates a strong return through offset expenses and improved capabilities.
• Improved IT Agility and Performance: IT departments can be more agile with an active SA strategy. New Version Rights ensure they always run supported, modern software, which typically means better performance, features, and security. This leads to downstream benefits like higher end-user productivity (e.g. employees using the latest Office 365 Pro Plus via SA have access to more collaboration tools), and reduced security incidents (because systems are up-to-date). Planning and deployment benefits result in smoother rollouts of new technology (less downtime, fewer rollout problems), accelerating time-to-value for new solutions. Additionally, by leveraging SA’s flexibility (such as license mobility and dual-use rights), these organizations can execute migrations or DR failovers with minimal hassle or cost. For example, in a disaster recovery scenario, a company with SA had pre-provisioned a passive failover SQL Server in a secondary data centre at no extra licensing cost. They failed seamlessly when the primary site went down, avoiding a major outage. That resilience and continuity is a practical benefit of having SA and using its terms wisely. In short, optimized SA usage translates to a smoother-running IT environment with fewer costly surprises.
• Support and Operational Efficiency: Organizations tapping into SA’s support structure are better prepared for incidents. Instead of paying per incident or hesitating to call Microsoft, their team leverages the included support (or uses the Unified Support credit) to resolve issues faster. This can significantly reduce downtime for critical systems. Moreover, well-trained staff (thanks to SA-funded training) manage and troubleshoot systems more effectively, leading to day-to-day operational efficiencies. The IT team isn’t scrambling to find budget approval for an urgent hotfix or consulting help – they have resources via SA. All of this contributes to a more proactive, stable IT operation, which, for a CIO, means fewer fires to fight and more time for innovation.

If SA is neglected or underutilized:

• Wasted Spend and Lost Value: The most immediate impact of not leveraging SA is waste. Companies paying for SA but not using the benefits are throwing money away. For example, consider an enterprise that spent a seven-figure sum on SA over three years but never used their training vouchers or planning days and delayed most upgrades. They’ve paid for service (maintenance and extras) and received little in return – effectively paying a premium on top of their license costs for nothing. This wasted value can be substantial; it directly affects the IT budget’s efficiency. Sourcing leaders may face tough questions when it becomes evident that “we paid for SA on 500 Windows Server licenses, but only upgraded 50 of them and didn’t use any of the training or support.” It’s like a gym membership you never use – the organization is left with a heavier cost with no fitness benefits. Over the years, this can accumulate into millions of dollars in opportunity costs.
• Higher Costs Elsewhere: Ironically, neglecting SA benefits often leads to spending more money through other channels. If you’re not using the included training, you might pay external training vendors for the same knowledge. If you don’t use the provided planning services or FastTrack, you might hire consultants for deployment guidance – again, paying extra for something your SA covered. Not paying attention to license mobility rights could mean you buy new licenses for a cloud project that existing ones could have covered. Or, if you ignore Azure Hybrid Benefit, you pay full price in Azure when you have credits you failed to apply. These “missed savings” show up as inflated project costs and cloud bills that could have been lower. Additionally, an organization that doesn’t upgrade via SA might need to purchase a new software version outright later – a capital expense that could have been avoided. For instance, skipping an Office upgrade and
  later buying Office 2025 for all users as a separate purchase will likely cost more than having kept SA and done it under that coverage. In short, underutilizing SA can make your overall IT spend higher than it needs to be, as you redundantly pay for software, services, or support.
• Operational Risks and Gaps: There are also less tangible but significant impacts on operations. A firm that doesn’t stay current because it ignores SA upgrade rights may run older, less secure software, potentially leading to security breaches or software that isn’t fully compatible with new systems. If you let SA lapse and a critical new feature or compliance requirement appears in the next software release, you might be caught unprepared (facing delays and unplanned costs to get that new version). Not using training benefits can leave skill gaps in your IT team, meaning slower issue resolution and lower adoption of new technologies. For example, if you deploy Windows 11 without using training vouchers or Microsoft Learn resources, your helpdesk and users might struggle with new features or changes, impacting productivity. Additionally, ignoring SA’s DR/HA rights could mean your IT architecture is less robust: maybe you didn’t set up that secondary server because you assumed you’d need another license, and then an outage hits. You suffer a longer downtime that could have been avoided. In terms of support, not leveraging included support incidents may slow down response to critical outages if the team hesitates to call Microsoft due to cost concerns, and precious hours could be lost. Overall, the consequence of neglecting SA is a less efficient IT environment, one that’s more costly and risk-prone than it should be. Over time, this can erode the confidence of stakeholders in IT’s ability to manage assets wisely and extract full value from vendor contracts.

To sum up, the practical impact of SA optimization vs. neglect is stark: companies that actively manage SA see better financial outcomes, higher utilization of their software assets, and smoother operations, whereas those that don’t will suffer unnecessary costs and potentially avoidable operational issues.

This contrast underscores why senior leaders must consider Software Assurance a discipline, not just a line-item cost.

Clear Recommendations

In light of the above, here are actionable recommendations for CIOs and sourcing leaders to maximize the value of Microsoft Software Assurance:

1. Conduct an SA Benefits Audit: Immediately task your IT asset management or software licensing team to catalogue every Software Assurance benefit your organization is entitled to. Map out which benefits have been used, which remain unused, and who in the organization is responsible for each. This audit creates awareness and is the foundation for improvement. (Include data centre and desktop SA benefits in the review – from server failover rights to Office Home Use Program availability.)
2. Create a Benefits Utilization Plan: To leverage each significant SA benefit, develop a plan (with owners and timelines). Schedule upgrades to new versions as part of your regular IT roadmap. Plan out training sessions or awareness campaigns to use learning resources. Line up FastTrack engagements or partner workshops for upcoming deployments. Essentially, treat SA benefits as projects to be executed, with the goal of zero wastage by the end of your agreement term. Review this plan quarterly to track progress.
3. Align SA with Strategy (No “One-Size-Fits-All”): Make SA renewal and usage decisions based on your business and cloud strategy. For each product line, ask: “Does continuing SA here support our plans?” If you are moving a workload to Azure or a SaaS app, outline how SA will facilitate that (e.g., through Hybrid Benefits or transition discounts) and when it might no longer be needed. If a system stays on-prem, ensure SA is maintained so you’re not caught on an outdated, unsupported version. In other words, tailor your SA portfolio to match your enterprise architecture plans – invest where it aligns and divest where it doesn’t.
4. Eliminate Redundant Spend: Use the findings from your analysis to cut out any overlap or waste. If you discover you’re paying for SA on products that duplicate capabilities you now get via Microsoft 365 or other subscriptions, plan to reduce or drop those at the next opportunity. If some benefits (like training or support) have alternates you already budgeted for elsewhere, consolidate them into the “free” SA-provided ones first. Every dollar of SA spend should have a purpose; if it doesn’t, reclaim it. Part of this step is also optimizing license counts – for example, don’t renew SA on 1,000 licenses if you only have 800 in use after a cloud migration. True-up or true-down wisely to fit actual needs.
5. Leverage SA in Vendor Negotiations: When your Microsoft renewal or true-up comes around, leverage the knowledge of your SA usage to negotiate better terms. If you’re a good customer who fully uses SA, highlight that and push to maximize its value (maybe ask for additional training passes or advisory hours to be bundled or better pricing on a needed product since you plan to keep investing in SA). If you are considering dropping certain SA elements, use that as leverage, too – Microsoft may offer concessions to keep that business. Always evaluate Microsoft’s proposals (like migrating to a new bundle or cloud service) through the lens of “Does this improve my value vs current SA setup?” and negotiate accordingly. Don’t passively accept standard renewals – engage Microsoft with data-driven requests (e.g., “We didn’t use X benefit that you removed, so we expect a cost adjustment” or “We want to trade these unused licenses’ SA toward Azure credits”). Negotiation is key to ensuring you get a fair deal and do not overpay relative to value.
6. Invest in Internal Expertise and External Advice: Ensure your internal licensing managers and procurement teams are well-versed in Software Assurance details – consider formal training or knowledge sharing on the intricacies of Microsoft licensing and SA (a complex domain that directly affects costs). Additionally, engage independent licensing experts to periodically review your strategy. An outside perspective (free of vendor sales motives) can identify improvements or validate that you’re on the right track. They can also assist in larger true-up negotiations or compliance checks, acting as your advocate. This combined approach – a knowledgeable internal team plus trusted external advisors – will keep you confident that you’re not leaving money on the table or taking on avoidable risks.
7. Implement Ongoing SA Governance: Treat Software Assurance management as an ongoing process, not a one-time task. Set up a governance rhythm: for example, a semi-annual SA value review meeting that includes IT, finance, and sourcing stakeholders. In these meetings, review which SA benefits have been utilized in the last 6 months, which are coming up, and any new developments from Microsoft that might affect your benefits. Track key metrics like “SA utilization rate” (e.g., percentage of available vouchers used, number of licenses upgraded, cloud savings achieved via SA, etc.). Keeping SA on the management agenda ensures continuous alignment with needs and can adjust quickly if something changes (like Microsoft altering a benefit or your company shifting strategy). Good governance will catch issues early, such as a benefit about expiring, so you can take corrective action. Over time, maximizing SA value is a standard operating procedure within your IT procurement and operations rather than an ad-hoc effort.

By following these recommendations, CIOs and sourcing leaders can systematically drive more value from Software Assurance. The key is to be deliberate and informed: know what you’re entitled to, use it fully, align it with your goals, and don’t hesitate to adjust or seek help. When managed in this manner, software assurance becomes a powerful tool to economically support the enterprise’s IT strategy, rather than just a renewal fee.