How to Build a Technology Strategy Worth Funding

"Only one in five companies believe they have high-quality strategy." 

McKinsey, How Strategy Champions Win

"Even with strategic alignment among IT and business leaders, technical and transformational initiatives still fall flat at an unacceptable rate."  

CIO.com, Why IT Projects Still Fail

​​"Despite $30–40 billion in enterprise investment into GenAI, this report uncovers a surprising result in that 95% of organizations are getting zero return"

MIT, The GenAI Divide STATE OF AI IN BUSINESS 2025

What these publications are referring to is not an edge case. It isn't a rarity. It is a widespread challenge and a reality across the industry. Defining and then effectively executing on a technology strategy has become increasingly and notoriously difficult with the proliferation of technology choices, tools, frameworks, and trends.

It could be platform modernization, IT strategy, AI strategy, or a large-scale system re-architecture. The challenges are the same.

The question is - why is it so seemingly difficult to build a cohesive and strong technology strategy and roadmap, and then execute on it productively once it is built?

In this article, we will explore the main reasons why IT strategy exercises fail and what are the ingredients that are absolutely necessary to create a successful IT Strategy, technology strategy, platform strategy, digital modernization plan, or AI strategy.

IT Strategy - The Main Failure Points 

IT Strategy Lacks a North Star

Building a technology strategy - whether for general IT, platforms, AI, or software applications, means that we are creating a direction. We are establishing where the organization is going and why it is doing so.

Without a clear North Star goal there is no clarity to that direction. Without a unifying vision, it is not possible to build an executable roadmap. Therefore, the strategy is bound to stall, peter out, or outright fail at some point. As a result, the organization will spend a significant time on trying to make sense of how to move forward - wasting resources and energy in the process.

Unclear Strategic Objectives

While establishing a unifying vision and north star goal for a technology strategy is the first and foremost order of business, it is not enough to build a strategy that the organization can follow through. 

The vision is just floating out there at the top of your technology strategy. However, it does not have any concreteness to it. Without putting colour to that vision, and without adding more details, the IT strategy will forever remain within the confines of your executive slide-decks. Shiny but frozen in time.

Lack of Executive Buy-In

It's often the case that an IT strategy is developed by someone at the senior director, VP, or SVP level - depending on whether that leader's unit is where IT is concentrated. The problem is that this strategy is often developed without consistent feedback and support from the executive team. The result is a strategy and, further down the line, a roadmap that is far detached from the reality of organizational value.

The executive team, business stakeholders, and senior leadership across the organization need to understand and align to what is being promoted by any given strategy. They need to understand and align on why we are going towards that North Star that we have put forth in building this specific IT strategy. They need to know where we are going and how we are going to get there.

Without this alignment and buy-in, there is no moving forward.

Forgetting to Assess Risks, Costs, and Value

When it comes to technology strategy, and AI strategy in particular, nowadays, everyone loves to paint the most positive picture possible. They talk about how their organization will be at the forefront of technology and innovation. How they will delight customers with new immersive products. And how much value the organization will get with barely any effort.

Few like to talk about the risks involved with going one way vs another. Even fewer like to talk about the costs each strategic initiative will bear. Furthermore, most forget about the most basic and fundamental requirement of every successful IT strategy and technology roadmap out there. You have to establish the value proposition. Without identifying the value and the return on investment (ROI) that you plan receive in the short and long term - you cannot know whether an investment in this or that initiative makes sense.

No Governance Model

When it comes to broad exercises like those involved with creating a technology strategy, AI strategy, or platform modernization roadmap - there is a lot of effort typically put at the onset. If done properly, the "strategy champion" talks to stakeholders, investigates the effort required, and leads workshops meant to build a unified and cohesive vision as well as a plan of execution. Getting this done. Packaging these deliverables for the C suite. Engaging stakeholders to create a shiny new roadmap. This is exciting stuff.

However, what comes next is arguably even more important though it may seem not nearly as riveting. 

We need to ensure that there is the proper structure for the IT strategy and technology roadmap to execute productively, optimally, and with minimal disruption. There needs to be scaffolding and guardrails in place to ensure that the exercise of executing on our strategy isn't derailed, and if it is - how it will be brought back on track. Risks need to be taken into account. Operating models established. The plan needs the right governance model with the right team, the right stakeholders, and the right framework to ensure success.

All too many technology strategy initiatives and programs have withered due to lack of proper governance or the inability to make it operational.

Not Involving Teams in Building the IT Strategy

Anything strategic is undoubtedly under the direct ownership of the leadership team - most often the Senior Leadership Team (SLT), the CEO, or adjacent functions.

So it is no wonder that so many organizations are pre-occupied with building an IT strategy that is completely driven from the top down and without the involvement of the teams who will actually execute on that strategy.

To position an IT strategy, digital transformation, modernization, or something as cutting edge as an AI strategy for success there has to be a push both from the top as well as from the bottom. Teams need to take an active part in defining that strategy so that it reflects the real needs and requirements of your organization.

Without involvement from the teams who will be living and working through our IT strategy, it will end up being devoid of meaning. It will look great on paper and executive slide decks. However, it's ability to put the organization on the path to success will be minimal at best.

The Framework to Craft an IT Strategy Worth Investing In

The problems called out above do not exist in isolation. They are typically interconnected as each one of these common pitfalls arises from another issue on this list. For example, the lack of a north star goal or shared vision commonly has a cascading effect on lower level goals - or, more precisely, the lack of thereof.

Similarly, not properly assessing risks, costs, and value is a major factor in failing to secure executive and stakeholder buy-in. Failing to get stakeholder alignment will, in turn, make it impossible to establish the right governance model and to get support for the teams who will be at the forefront of implementing the technology, modernization, or AI strategy.

The way to craft a strong technology strategy that will be set up for success and secured by a real and executable roadmap is to incorporate the necessary components that flesh out its different levels.

There are many ways to do so and each organization will have its own context and nuances that will feed into each specific approach. That being said, there are some fundamental elements or layers of the strategy building exercise that need to be addressed holistically as we go through establishing said strategy.

Think of the exercise of building an IT strategy and accompanying roadmap as interconnected layers.

Executive Intent

This layer captures why the organization is investing in technology in the first place. It reflects business ambition, competitive positioning, risk appetite, and the outcomes leadership cares about most. This is your North Star.

When this layer is unclear or interpreted inconsistently across the organization, everything beneath it becomes unstable. Teams may execute efficiently. However, they will execute in directions that do not meaningfully advance the organization’s goals.

Strategic Objectives and Constraints

Below intent sits the layer where ambition is turned into commitment.

This is where priorities are set, trade-offs are acknowledged, and constraints are made explicit. This is where we begin thinking of costs even though they will be primarily high level at this point. It defines what matters most, what matters less, and what the organization is deliberately choosing not to pursue.

This is where we start turning our vision into something more concrete. Without this layer, vision remains aspirational at best.

Business and Capability Realities

This layer represents how the organization actually functions today. This is where we assess the current state with all of its constraints and capabilities.

It encompasses existing capabilities, processes, dependencies, and operational realities that shape what is feasible. 

Strategies that ignore this layer tend to overestimate speed, underestimate complexity, and struggle to gain traction once execution begins. They certainly will struggle to show value as they unfold.

Technology Foundations

At this stage, we surface the platforms, systems, data, and architectural foundations that enable or constrain change. This is where we flesh out our IT strategy to its components and begin getting into the specific details that will make or break our IT roadmaps.

This layer determines what can or needs to be built, integrated, scaled, and secured. It includes legacy systems, emerging platforms, and architectural decisions that may have been made years earlier but still exert influence today.

While this layer may feel like it is disconnected from higher-level strategy, without it - organizations often invest heavily in modernization without a clear sense of why or to what end.

Organizational and Operating Model Readiness

Technology strategies do not execute themselves.

This layer reflects how work gets done: team structures, decision rights, governance models, skills, responsibility matrices (RASCI, for example), and incentives. It determines whether the organization is actually capable of executing the roadmap it has defined.

Even the most coherent strategy will stall if this layer is not aligned with the pace and nature of the changes being proposed under our specific organizational context. 

Delivery and Sequencing

This layer translates all of the above into concrete initiatives, sequencing, dependencies, and timelines. It calls out detailed risks, costs, implications, and the "why" behind each initiative. It is where strategy becomes fully tangible, and where misalignment across layers becomes visible very quickly.

When delivery struggles, we can often find the root cause higher up in one of the upper layers that shaped it.

Technology Strategy Layers - Key Takeaways

The key to the  layered approach above is that these layers are interconnected. Although you need to address the top layer before tackling the next one, you will be going back and forth throughout this exercise of establishing and setting in motion your IT strategy.

There will be elements within these layers, especially at the bottom ones, that will constantly shift and fluctuate in terms of initiatives, dependencies, risks, and other lower level elements. At the same time, much of the topmost elements such as the vision and strategic goals will commonly remain the same or with little change. If they do change, this will cause a trickle down effect down the stream to all the layers that follow.

To position your technology strategy for success, it is imperative to ensure that it evolves in the right places and at the same time remains true to its foundations. 

Success depends both on the individual layers and their interconnectedness as well as how well they are understood, aligned, and reinforced over time.

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CloudWay Digital is an advisory that helps organizations build cohesive, concrete, and executable technology strategies and roadmaps. If your organization is struggling with defining its IT strategy, AI strategy, or platform modernization, it may be worth chatting with us.

Technology strategy is often tightly interconnected with software and enterprise architecture. Yet, many technology architects fell unhappy, inefficient, or unfulfilled in their roles, and therefore, are not set up for success within the organization. The Unlocking the Career of Software Architect guide helps technology and software architects grow, thrive, and succeed in their career as well as provide them with the tools to bring the most value in their role.