No, the Role of an IT Strategy Is Not to Please the Business

Recently, we worked with the Health & Benefits division of a leading insurance broker to redefine its IT Strategy, in a situation that will feel familiar to many insurance industry executives. On one side, business expectations continue to grow: accelerating operational processes, improving service quality, unlocking more value from data, preparing the organization for AI-enabled use cases, reducing time-to-market, and supporting ambitious growth plans.

On the other side, the information system bears the scars of decades of successive layers of complexity. Incidents are increasing, teams spend most of their energy keeping legacy systems running, every change becomes more complex than expected, and some critical capabilities depend on a very small number of experts. As is often the case in the insurance industry, the issue goes far beyond IT performance. When incidents affect core operations, customer journeys, or business processes, service quality deteriorates, operational efficiency suffers, and growth itself can be impacted.

Adding to this is a situation many organizations are facing today: a new financial shareholder and the beginning of a new value-creation cycle, bringing heightened expectations around cost control, operational performance, integration capabilities, governance, and scalability. In short, expectations of the information system are increasing at exactly the moment when the resources available to transform it are becoming more constrained. The natural response is to deliver what the business asks for. Yet in this context, saying yes to every business priority often weakens the organization’s ability to transform. This is the paradox many insurers now face, and it raises a question that is rarely asked explicitly: Should the IT Strategy be driven by business priorities, or should it place limits on them?

The Real Cost of Obsolescence Is the Loss of Strategic Freedom

When organizations discuss obsolescence, they usually focus on technology: outdated software versions, legacy architectures, technical debt, security vulnerabilities, or poor maintainability. All of these concerns are real but they are not the core issue. The true cost of obsolescence is not technical, it is strategic.

Aging information systems create consequences that eventually affect every part of the business:

  • Increasing incidents
  • Teams consumed by operational support activities
  • Rising maintenance costs
  • Reduced control over delivery timelines
  • Dependence on a handful of long-serving experts
  • Growing difficulty adopting new capabilities

From this perspective, the true measure of obsolescence is not the age of your applications, but the number of decisions your organization can no longer make.

When a valuable business initiative is postponed because it would require six months of impact analysis, complex developments, or endless testing, the problem is no longer architectural. It is a matter of strategic freedom. The business may still have ambitious objectives, but the information system no longer has the capacity to support them.

When a Good Business Idea Becomes a Bad Collective Decision

In a healthy environment, the logic seems straightforward: business teams express their needs, IT prioritizes them, the most valuable initiatives are delivered, and everyone moves forward. But this dynamic can quickly break down. When the information system becomes fragile, not all business requests have the same consequences. That does not mean some requests are legitimate and others are not. Most address genuine business needs.

However, some initiatives create more value than they consume transformation capacity, while others do the exact opposite:

  • A highly anticipated feature may introduce another layer of complexity.
  • An urgent development may deepen an already problematic technology dependency.
  • A perfectly justified business requirement may move the organization further away from its target state.

This is where tensions emerge, business teams see an opportunity, IT sees another point of failure : both are right. No meaningful prioritization can be achieved by looking only at immediate business value. In a highly constrained technology environment, organizations must also assess:

  • The impact on technical debt
  • The consumption of scarce resources
  • Compatibility with the future technology foundation
  • Component reusability
  • The risk of creating additional workarounds and exceptions

An initiative can be highly beneficial for one business function and harmful for the company as a whole. That reality is difficult to accept, but ignoring it is far more costly.

Choosing Means Letting Go: An IT Strategy Is an Exercise in Strategic Discipline

For many years, an IT Strategy followed a familiar pattern: Target state → roadmap → portfolio of initiatives → delivery plan

That approach works when an organization has sufficient room for manoeuvre. But when resources become scarce and obsolescence significantly constrains execution capacity, the nature of the exercise changes. The IT Strategy is no longer a catalogue of initiatives. It becomes a tool for making trade-offs. Its role is no longer simply to define what should be done. It must also clarify what the organization is willing to postpone, simplify, address temporarily, or stop pursuing altogether. It must determine which investments should take priority in order to restore the underlying technology foundation. In other words, the IT Strategy organizes the trade-offs required to restore transformation capacity. The concept may not be popular, but every strategy is built on choices, and choices inevitably mean giving something up. Some short-term opportunities must be declined in order to preserve long-term transformation capacity.

AI Ruthlessly Exposes What Organizations Have Refused to See

The rapid rise of Data and AI initiatives introduces another layer of tension. Expectations are understandably high:

  • Automated operations
  • Improved customer experiences
  • Predictive decision-making
  • Fraud and anomaly detection
  • Process optimization
  • Personalized services

The opportunities are real. But they all rely on the same assumption: that a solid foundation is already in place.

That foundation includes:

  • Accessible data
  • Reliable master data
  • Standardized processes
  • Controlled information flows
  • A coherent architecture

In reality, many information systems are still far from that position. Data remains fragmented. Manual workarounds persist. Shadow spreadsheets proliferate. Business rules are duplicated. Traceability is incomplete. AI will not fix these weaknesses. It will simply expose them faster and more dramatically.

Restoring Transformation Capacity

The debate is not between business teams and IT. The debate is ultimately about balancing short-term delivery with long-term transformation. Both perspectives are legitimate. The challenge lies in reconciling them. This is precisely where the IT Strategy regains its true value: as a governance tool that provides a framework for collective decision-making. The question is not whether the IT Strategy should follow business priorities or constrain them. The real question is: Which constraints are we willing to accept today in order to regain the freedom to transform tomorrow? How do you build a shared vision when every stakeholder sees the problem through a different lens? This is where an IT Strategy succeeds or fails. At Talisker, we believe an IT Strategy only creates value when it becomes a tool for decision-making, alignment, and action. A target operating model, no matter how well designed, is meaningless if the organization cannot understand it, commit to it, and execute it collectively. That is where transformation truly begins. It is also the conversation we most enjoy having with executives, CIOs, and business leaders facing these challenges.

Let’s talk: https://www.linkedin.com/in/nicolas-riboud-sainclair-648a1b67/