How to Build an IT Roadmap When Your Vendors Aren’t Ready

Tina Marie Baugh
Sep 19
6 min read

Updated: Oct 18

Every IT leader sets out with the same intent: to build a roadmap that modernizes systems, reduces risk, and positions the organization for growth. It’s the blueprint for how technology aligns with the business. But in highly regulated industries like healthcare, airlines, or banking, that neat and forward-looking plan quickly collides with a stubborn reality: your vendors don’t always keep pace.

Your IT roadmap points forward.

Your vendor roadmap points sideways—or sometimes backwards.

And that tension isn’t just frustrating. It can derail strategy, introduce risk, and leave your team explaining to executives why a “simple” upgrade is anything but.

Why Vendors Lag in Regulated Industries

Vendor lag usually comes down to two forces: regulation and investment.

In healthcare, systems tied to diagnostic testing or medical devices can’t be updated on a whim. A software release may need FDA review, which stretches timelines from months into years. In airlines, the FAA enforces strict approvals before flight systems can be changed. In banking, compliance audits and financial regulations create layers of checks before any upgrade can go live.

Then there’s the investment side. Vendors may not have the appetite—or the funding—to rebuild legacy systems that thousands of customers still rely on. Re-architecting for cloud or rewriting code bases costs millions. So vendors stabilize instead of modernize, leaving customers stuck with outdated stacks.

For IT leaders, the impact is the same: you’re trying to steer the business forward with tools that keep dragging you back.

The Real Cost of Misaligned Roadmaps

This gap between IT and vendor roadmaps isn’t just a nuisance—it has real consequences. Four of them show up consistently.

Security Risk Increases

When vendors delay upgrades, systems often sit on unsupported operating systems or databases. The security exposure is obvious, but the fix isn’t always in your control. IT leaders end up relying on compensating controls to mitigate risk: segmenting networks, tightening access, and building custom monitoring.

These band-aids work—but they add weight. Every layer of control increases complexity. And the more complex a security environment becomes, the harder it is to sustain. Teams spend countless hours patching around vendor gaps rather than focusing on proactive security.

Even worse, regulatory auditors and boards rarely accept “our vendor isn’t ready yet” as a full excuse. Leaders must demonstrate they understand the risk and have a strategy in place, even if it means carrying legacy exposure longer than anyone would like.

Cloud Strategies Stall

Many organizations today are “cloud-first” in name and strategy. But vendors that lag behind in cloud readiness force leaders to maintain on-premises systems long past their planned retirement date. The impact goes far beyond slowed innovation—it drives up operating costs.

Instead of leveraging elastic cloud recovery, IT teams must fund and maintain expensive disaster recovery solutions for legacy platforms. Backup and recovery exercises—processes that can often be scripted or automated in the cloud—become heavy, manual, and resource-intensive.

High-availability configurations require duplicate infrastructure, licensing, and support contracts—sometimes across multiple colocation facilities. Each layer adds cost without adding future value. What should be a simple, repeatable recovery drill in the cloud becomes a high-cost, high-risk event every time.

Meanwhile, the business questions why the cloud strategy seems stalled, leaving IT leaders to explain that “our vendors aren’t ready” is not a lack of vision—it’s a constraint of the ecosystem.

Costs Multiply in the Shadows

Every time you keep an outdated platform alive, hidden costs pile up. Skilled staff spend more time babysitting fragile integrations. Recruiting becomes harder when you’re asking engineers to maintain technologies their peers have long abandoned. Vendors charge premiums for extended support on out-of-date products.

None of these costs typically show up in the project budget. They creep in through overtime, consulting hours, retention challenges, and operational inefficiencies. Leaders who don’t account for these hidden costs risk underestimating the total burden of vendor lag—and overspending on “keeping the lights on” instead of building for the future.

This is where financial literacy for IT leaders becomes critical. Being able to articulate these costs—both direct and hidden—helps executives understand why sticking with the status quo is often more expensive than pushing for change.

Executive Trust is Tested

Perhaps the hardest cost to measure is credibility. Executives and boards rely on IT leaders to deliver clarity and progress. When roadmaps repeatedly shift because vendors are late, trust can erode.

The key here is transparency. Leaders who present both the ideal roadmap and the vendor-constrained version set realistic expectations. They show executives not just what’s possible, but what’s dependent on external timelines.

By documenting risks, trade-offs, and compensating measures, IT leaders turn a difficult message into a managed plan. Instead of appearing reactive or unprepared, they demonstrate foresight—even when the outcomes are constrained. In other words, credibility isn’t lost because vendors are behind; it’s lost when leaders pretend the lag doesn’t exist.

Three Ways Forward

While IT leaders can’t erase vendor lag, they can lead through it with three deliberate approaches.

Anchor Roadmaps to Business Priorities

It’s tempting to measure success by version numbers or release dates, but technology maturity is never the end goal. The real driver is business outcomes—resiliency, security, agility, efficiency.

When you anchor your roadmap to those priorities, vendor timelines become a constraint, not the definition of success. For example, if resiliency is the priority, you may not be able to upgrade to the vendor’s latest version, but you can strengthen disaster recovery processes, implement compensating controls, and build monitoring that demonstrates progress. If cost efficiency is the goal, you can still consolidate overlapping systems or renegotiate contracts, even if a critical application is stuck on an older OS.

By continually tying the roadmap to business priorities, IT leaders keep the conversation focused on value, not on which patch level a vendor has reached. This creates trust with executives because you’re delivering outcomes the business can see—even when vendor roadmaps lag.

Plan in Two Realities

Plan two tracks: Ideal and vendor-constrained

The best IT leaders learn to work in parallel. On one track sits the ideal roadmap: the cloud migrations, modernization efforts, and upgrades that represent the best technical path forward. On the other track sits the vendor-constrained roadmap: the adjustments you must make because a vendor is behind, a system is locked, or a regulatory cycle slows release.

Both realities matter. The ideal roadmap demonstrates vision. The vendor-constrained roadmap demonstrates pragmatism. When you show both, you’re not hiding limitations—you’re exposing them with clarity. That transparency allows executives to understand where trade-offs exist and why.

For example, you might explain: “Here’s the cloud-first path we want to take. But because our core vendor won’t support Azure until 2027, here’s the constrained plan, and here’s the additional cost of staying on-prem for three more years.” With that framing, executives see the gap, the risk, and the business impact. They’re empowered to make informed decisions rather than feeling blindsided later.

This dual planning is harder, but it’s what earns IT leaders credibility. It shows that you’re managing reality, not just describing aspiration.

Influence, Don’t Accept

You may not control vendor roadmaps, but you’re not powerless. Influence comes in several forms.

Push for transparency. Instead of accepting “we’re working on it,” press vendors for specific timelines, regulatory hurdles, and investment plans. Even partial visibility helps you plan better.

Leverage advisory boards and customer councils. Vendors listen more closely when multiple clients raise the same concerns. By joining these forums, you amplify your organization’s voice and sometimes shape vendor priorities.

Use contract renewals as pressure points. The best time to negotiate roadmap alignment is when a vendor wants your signature for another three years. Ask for commitments on support timelines, cloud readiness, or modernization milestones as part of the deal.

Finally, build peer alliances within your industry. Healthcare leaders face one set of vendors and FDA requirements. Banks navigate a different ecosystem of providers and regulators. Airlines deal with their own FAA-driven constraints. By coordinating within your industry, you create a unified front that carries far more weight than any single organization trying to push change alone.

Leading Through the Tension

The gap between vendor and IT roadmaps won’t disappear anytime soon. But leaders who anchor roadmaps to business priorities, plan in two realities, and influence vendors with intention can navigate the gap without losing momentum.

Leadership isn’t about waiting for perfect conditions. It’s about guiding your organization forward—even when the path is constrained. At the end of the day, it’s not about waiting for vendors to catch up. It’s about leading your business confidently through the in-between.

💡 Your turn: Which of these three approaches—anchoring to priorities, planning in dual realities, or influencing vendors—has been the hardest in your world?