Gartner series #1- Agents of Change Don’t Just Upgrade—They Transform
September 15, 2025
6 min read
September 15, 2025
6 min read
Every executive team today talks about transformation. Artificial intelligence, automation, and analytics dominate strategic roadmaps and board agendas. Yet inside many enterprises, the initiatives meant to move the business forward struggle to breathe. Budgets are consumed by a familiar cycle of vendor-dictated upgrades, forced migrations, and routine change activities that present themselves as essential while delivering marginal business impact. The outcome is paradoxical: at the very moment when organizations must become more innovative, more agile, and more data-driven, their resources are tied up keeping pace with someone else’s calendar.
Origina CEO Tomás O’Leary captured this pattern in his recent Forbes Technology Council article, “How Organizations Are Creating Space For True Transformation By Shrinking Their Change Budget.” The core message is plain: innovation cannot thrive if an enterprise treats upgrade notices as destiny. Leaders who want to transform must first reclaim the time, money, and talent that upgrade cycles quietly drain.
A helpful way to see the problem is through a simple model of three buckets. The run bucket contains the systems that keep the business operating—the applications, platforms, and integrations that process transactions, orchestrate supply chains, and serve customers daily. The change bucket holds upgrades, patches, and migrations—activities that are often justified in the name of risk management or vendor alignment. The transform bucket funds the work that actually changes competitive position: deploying AI to re-design a process, modernizing a service experience, automating a workflow that previously required human intervention.
In principle, these buckets are meant to coexist. In practice, the change bucket expands almost imperceptibly year after year. As estates grow more complex, as vendors deprecate older versions and as organizations add layers of tooling to keep pace, the proportion of spend devoted to change rises. The run bucket stays largely stable; the transform bucket is expected to do more with less. What suffers is not only the speed of innovation but the energy of the people who would otherwise be advancing it.
The direct costs of upgrades are well understood: licenses, labor, testing environments, rollbacks and emergency fixes when something breaks in production. The less visible costs are the most corrosive. Every major migration pulls engineers, architects and product-minded technologists into weeks or months of work that rarely changes a customer outcome. Teams postpone experiments, cancel proofs of concept and shelve ideas because they are consumed with remediation. Leaders rightly ask for stability, but the price of that stability is too often paid with the currency of opportunity.
There is also a cultural cost. When the most capable people spend the majority of their time managing version changes, they begin to identify as caretakers rather than creators. The organization internalizes a belief that IT is a cost to be minimized, not a source of strategic advantage. That belief becomes self-fulfilling: fewer transformative ideas are proposed, fewer are funded, and the enterprise slowly falls behind competitors who allocate talent differently.
Breaking this pattern is not about negligence; it is about leadership. “End of support” does not automatically equal “mandatory upgrade.” Intelligent leadership treats vendor timelines as one input among many and asks a more rigorous set of questions. What measurable business value will this change create? How will it reduce a specific risk we actually face, at a level proportionate to that risk? What customer outcome will improve, and by how much? If the answers are unclear, leaders explore alternatives that protect the business without consuming transformation capacity.
Those alternatives exist. Independent support models can maintain stability and security for mature systems without forcing a full migration. Targeted engineering can often deliver the capability that triggered an upgrade—such as a crypto library update or an integration endpoint change—without touching the surrounding estate. Risk-based maintenance allows teams to stratify applications by criticality and exposure, directing attention and funding where they matter most. None of this is about ignoring risk. It is about calibrating response, so that change serves strategy rather than the other way around.
Compliance conversations can harden into ritual. A vendor announces an obsolescence date, an audit clause is cited, and the assumption is that the “safe” path is a wholesale move to a newer version. Yet every large-scale upgrade introduces its own operational and cyber risk: new attack surfaces, new misconfigurations, new regressions, and new integration fragility. The safest posture is not perpetual change; it is intelligent change governed by business context.
Leaders who reframe risk this way discover they can maintain or even improve their security posture while minimizing disruption. They invest in the controls that matter—hardening, monitoring, segmentation, configuration assurance—rather than assuming that new equals safer. In doing so, they also preserve budget and attention for the truly strategic work: modernizing a customer journey, embedding AI into decision flows, and automating manual handoffs that slow the business down.
Budget is the visible resource reclaimed when the change bucket shrinks. Talent is the multiplier. Engineers who are not locked in an upgrade treadmill think differently. They look for ways to apply machine learning to noise-heavy processes. They challenge assumptions buried in legacy workflows. They prototype, measure and iterate. They collaborate more closely with product and operations, because they are not fire-drilling rollouts. The psychological shift is as important as the practical one: teams rediscover that their work can change outcomes, not merely preserve them.
This is where culture intersects with strategy. If leaders want a high-initiative, experimentation-friendly environment, they must remove the obstacles that train people to play defense. Shrinking the change bucket is one of the most powerful cultural signals an executive team can send. It says, explicitly, that transformation is not a slogan. It is the job.
Although the mechanics of upgrades sit with IT, the mandate to rebalance spend belongs to the CEO. Technology leaders can present options, quantify trade-offs and propose risk-based approaches. Only the chief executive can insist that the company’s capital be deployed in service of competitive advantage rather than vendor cadence. That insistence takes the form of better questions. What would we fund if we redirected a fixed percentage of change spend toward transformation each quarter? Which customer outcomes could we impact in the next six months if our best engineers were not tied up in migration work? How will we measure whether an upgrade produced real value beyond compliance?
When CEOs ask questions like these, they give CIOs and CFOs permission to think differently. The planning process expands beyond a single path. Boards begin to see that independence is not recklessness; it is stewardship. Over time, the organization learns to separate myth from mandate and to allocate resources like a company intent on leading its market.
The practical path forward starts with visibility. Organizations need an honest inventory of where change spend goes today, and why. They need to separate changes that reduce material risk from those that simply align with vendor preferences. They need a narrative that the business can understand: here is what we will not change this year and why; here is how we will keep it secure; here is the capacity we will free and the initiatives we will fund with it.
From there, executives pilot the new operating rhythm. They select a candidate system where a targeted enhancement can displace a large upgrade, or where independent support can maintain stability while teams focus on building something new. They capture the savings, quantify the risk outcomes and, crucially, celebrate what the team delivered with the capacity they reclaimed. The story begins to tell itself. Momentum grows, not because change is avoided, but because change is finally being applied intelligently.
The Symposium’s theme—Agents of Change: Leading Through Intelligence—is a call to this kind of leadership. It is an invitation to stop equating activity with progress and to start funding the work that moves the needle for customers and shareholders. It recognizes that the greatest constraint on transformation is not technology; it is attention. Enterprises have more tools than ever, but the attention of their best people is finite. Leaders decide where that attention goes.
When executives gather in October, the most valuable conversations will not be about which platform is newest. They will be about how to structure operating models so that new capabilities can be absorbed, scaled and sustained. They will be about the discipline to say no to low-value change and yes to initiatives that create advantage.
Enterprises that thrive in the next decade will adopt a new formula for resource allocation: run remains stable, change shrinks and transform expands. The formula is simple, but it requires courage. It requires the willingness to challenge assumptions that feel safe and to trust teams to design targeted solutions when the textbook answer is an overhaul. It requires leaders to measure success by outcomes rather than compliance.
Make that shift, and transformation gains oxygen. Customer experiences improve because funding and talent are available to redesign them. Risk posture strengthens because effort is focused on the controls that matter. Teams become more ambitious because they see that ideas can become reality. In short, the organization begins to act like the kind of company its strategies describe.
The AI revolution will not pause while enterprises complete another lap on the upgrade track. The organizations that lead will be those that reclaim their resources, redeploy their talent and reassert that business outcomes—not vendor rhythms—set the pace. That is what it means to lead through intelligence.
Agents of change don’t just upgrade—they transform.
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