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Thought Leadership

Your IT strategy looks solid. But has anyone tried to break it?

Author :
Ken Thomson

At Leading Resolutions, we have sat in plenty of rooms where an IT strategy is presented to a technology team, executive leadership or the board.
The audience may change, but the pattern is often familiar.

The slides are polished. The roadmap looks logical. The investment case appears sound. There are questions, some debate and, eventually, agreement on the way forward.

Everyone leaves believing progress has been made.

Then delivery begins.

Costs increase. Timescales move. Dependencies emerge that were not fully understood. The chosen technology does not fit quite as well as expected. The organisation struggles to provide the people, capacity or capability assumed in the plan.

In hindsight, the warning signs were there. They simply were not visible to the people closest to the strategy.

How blind spots develop

When an IT strategy is developed internally, it naturally draws on what the organisation already knows: incumbent vendors, familiar technologies and the skills available within the business.

It is also shaped by existing investment decisions, organisational priorities and internal dynamics. These factors can influence which options are considered realistic and which are discounted before they are properly explored.

None of this suggests poor judgement or a lack of capability.

Internal knowledge is essential. The people within the organisation understand its history, constraints and ambitions better than anyone. But familiarity can also create blind spots, particularly when assumptions become accepted as facts.

“We will use the platform we already have.”
“The team will adapt.”
“We can recruit the skills we need.”
“We should be able to deliver this within 12 months.”

Individually, each assumption may be reasonable. Collectively, they can make a strategy look more certain than it really is.

We have worked with organisations where the strategy was well considered, technically coherent and developed by capable people. Yet some fundamental questions had not been asked. Not because the team lacked the ability to ask them, but because nobody outside the work had been invited to challenge the thinking.

What should an independent review test?

Seeking an independent view does not mean the strategy is wrong. It means the organisation wants to test its thinking before making decisions that may be difficult or expensive to reverse.

A good review should not simply validate the document. It should examine the assumptions behind it.

Are the Technology choices right?

Technology decisions are rarely made in a vacuum. Existing relationships, previous investments and team experience all influence the options that reach the shortlist.

Sometimes the preferred choice remains the right one. But that conclusion is stronger when the alternatives have been properly tested and the evaluation criteria have not unintentionally favoured the most familiar option.

We recently worked with an organisation that had identified a preferred ERP platform. The initial choice appeared credible, but a deeper review of the requirements and available alternatives identified a substantially better fit.

The purpose of the challenge was not to overturn the original decision. It was to ensure the organisation made the right one.

Are the costs complete and realistic?

The headline cost of a transformation rarely tells the whole story.

Licensing may change as usage grows. Old and new systems may need to run together. Productivity can fall while teams learn new processes. Additional support may be needed after go-live. Internal people assigned to the programme still represent a cost to the wider business.

These costs are not always omitted deliberately. They are often difficult to see from inside the programme.

Benchmarking the assumptions against comparable transformations can expose gaps before they become budget pressures.

Can the timescale hold?

A confident roadmap can quickly become an unrealistic one if important dependencies have been underestimated.

Delivery may rely on scarce internal resources, third parties, data readiness, procurement, governance decisions or other programmes completing work on time.

A realistic plan should make those dependencies visible. It should also show where there is genuine contingency and where a date depends on everything going right.

An achievable timeline is more valuable than an ambitious one that begins to unravel as soon as delivery starts.

Does the organisation have the capacity to deliver?

Strategies often depend on people or capabilities that are not yet in place.

The plan may assume that new roles will be recruited, specialist knowledge will be developed or existing teams will find additional capacity alongside their day-to-day responsibilities.

Those assumptions need to be tested early.

What happens if recruitment takes longer than expected? What will be deprioritised to release internal capacity? Where will the organisation need external support? Who will retain the knowledge after delivery?

A strategy is only credible if the organisation can realistically mobilise the people needed to deliver it.

Is the future operating model clear? 

Technology strategies tend to describe what will be implemented. They do not always explain clearly enough how the organisation will operate afterwards.

Who will own the new platforms? How will they be supported? Which capabilities will sit internally and which will be provided by partners? How will decisions be made? Who will be accountable for improving the technology once the programme team has moved on?

Without clear answers, an organisation can successfully implement new technology but still struggle to realise the expected benefit.

Is there a credible plan for bringing people with you?

Technology transformation changes how people work. That change cannot be treated as an activity to address shortly before go-live.

Communication, engagement, training and adoption should be designed into the strategy from the start. They require clear ownership, sufficient investment and the same attention as the technical delivery.

A platform can be implemented exactly as designed and still fall short if people do not understand it, use it consistently or see how it improves their work.

This is not about competence. It is about proximity.

The people who develop a strategy have usually invested considerable time, judgement and credibility in it. They have explained it to colleagues, presented it to leadership and built support for the proposed direction.

Naturally, they want it to succeed.

That commitment is valuable, but it can also make it harder to step back and question the underlying thinking.

An independent reviewer does not carry the same history. They have not previously defended the recommendation or built the business case around it. They can test the choices and assumptions without needing to protect the original answer.

That distance is difficult to create internally, even with strong governance and capable people.

Challenge the strategy while there are still choices

Independent scrutiny is most valuable before major commitments are made.

Once contracts have been signed, delivery teams mobilised and expectations set, changing direction becomes more disruptive and expensive.

A review undertaken while the strategy is still being shaped can improve decisions, expose risk and strengthen the plan. A review carried out after delivery has gone off track is a very different exercise.

If your organisation is developing an IT strategy, or has recently approved one, it is worth asking a simple question:

Has anyone who was not involved in writing it been asked to find the weaknesses in it?

At Leading Resolutions, we provide independent challenge to help organisations make better technology decisions. We test the thinking, examine the assumptions and identify the issues that can otherwise remain hidden until delivery begins.

Because the best time to challenge an IT strategy is while you still have choices.

The Author

Ken Thomson is a Client Partner at Leading Resolutions, where he helps organisations develop pragmatic technology strategies that align with business goals and deliver measurable value. His experience spans technology leadership, transformation delivery and advising boards on some of their most critical decisions