What two decades of technology transformation taught me about why organisations resist their own strategies
16 April 2026

I learned to think of strategy as a political process in the classroom before I could refine it in practice in the boardroom. Andrew Pettigrew taught the strategy module on my MBA, and his core argument stayed with me long after the programme ended: the moment someone raises a problem, the strategy process has already begun. Behaviour precedes intention. Change is not a sequence that starts with a plan. It starts the moment tension becomes visible — and the real question is whether the organisation treats that tension as a signal or as a threat.

Since then, I have spent years leading change and transformation initiatives in the technology sector, working across a wide range of customers. What I have seen consistently is that the technical challenge is rarely the hard part. The hard part is the politics. Every transformation redistributes power, and the people who stand to lose it can see it coming long before the project plan lands in their inbox.

Organisations do not resist change. Individuals within them resist the specific losses that change implies.

The gatekeeper problem

Pettigrew framed strategy as simultaneously a change, influence, and political process. The political dimension is the one most project teams are least equipped to navigate. I saw this play out clearly while working with one of the UK’s largest retailers on a digital transformation programme. They were migrating from a legacy Access database to a cloud-based Salesforce CRM system — a move that would give the wider organisation direct access to data, insight, and campaign tools that had previously been controlled by a single individual.

That individual was a long-standing contractor who had managed the existing database for decades. They knew the system intimately. They had shaped its structure. They had become, in effect, a single point of failure that the organisation had learned to work around rather than address. The migration threatened all of it — not the person’s competence, but their position. Moving to an accessible, cloud-based system meant the organisation’s dependency on this one person would disappear.

The contractor still controlled the live database that powered ongoing work, which meant they could slow progress, question decisions, and create friction at every integration point. The project could not move forward without their cooperation, and their cooperation was conditional on a future that still included them.

What shifted this was a deliberate redesign. We brought the individual into the design process for the new system, gave them a meaningful role in shaping the structure of the Salesforce CRM environment, and defined a post-go-live position that preserved their expertise in a new context. The resistance did not vanish, but it became manageable once the person could see a version of the future where they still mattered.

As Pettigrew put it, change is political because some gain power and some lose it.

What I learned in this case is that sometimes the work is not about overcoming resistance but about redefining what power looks like in the new world — so that those who feel exposed can find a footing that does not depend on blocking everyone else.

When the incentives say the quiet part out loud

If the retail case was about an individual protecting their position, a second experience with one of the UK’s largest energy providers revealed something more systemic. I was working to consolidate requirements across a distributed set of stakeholders — departments that needed to align on a shared platform. The challenge was that each stakeholder was optimising for their own function rather than for the organisation.

One stakeholder made this explicit. In a meeting, they said, “Thanks for all the work you’re doing. I recognise you’re trying to do what’s best for the organisation, but what I care about is what’s best for my department.”

There was no ambiguity. This person understood the politics clearly. They knew that the organisation’s incentive structure rewarded departmental performance, and they were responding rationally to that structure. If their department succeeded — even at the expense of other departments — they would be recognised for it. There was no reward for collective progress and no penalty for undermining it.

This is Pettigrew’s misaligned incentives lens in its purest form. The stated strategy was enterprise-wide transformation. The revealed strategy — visible in the reward system, the performance metrics, the promotion criteria — was departmental competition. When those two signals conflict, people follow the incentive rather than the strategy deck.

The structural answer is straightforward in theory and difficult in practice: redesign the reward system so that collective outcomes carry weight. If individuals are measured and rewarded only at the functional level, they will optimise at the functional level. If there is a meaningful organisational reward — one that connects personal success to enterprise success — the equation changes. But this requires executive sponsorship with sufficient authority to redesign incentive structures, not just to commission a transformation programme.

Reward systems are the organisation’s revealed strategy. If they do not change, nothing else does.

The pattern underneath

Both cases share a common structure. In each, the technical change was understood and broadly supported at a strategic level. In each, progress stalled not because of capability gaps but because of political dynamics that the project governance was not designed to surface or address. And in each, the path forward required something beyond better planning — it required confronting the way power, dependency, and incentives actually operated within the organisation.

Pettigrew’s framework — context, content, process, time — remains the most useful lens I have found for reading these situations. Most change programmes over-invest in content, the “what,” and under-invest in understanding the inner context: the political norms, legacy relationships, and cultural assumptions that determine whether a change will be absorbed or rejected. Dealing with what is harder than dealing with the how, because the how is a design problem. What forces you to sit with competing interests and make choices that not everyone will welcome.

The organisations that succeed at transformation are not often the ones with the best technology or the most detailed plans. They are the ones willing to treat change as a political arena, to name the power dynamics rather than pretend they do not exist, and to redesign the systems — especially the reward systems — that tell people what the organisation actually values. Smart power, as Joseph Nye defined it, is not hard or soft. It is the judgment to know which context demands which response. After two decades of watching change programmes succeed and fail across the technology sector, I am convinced the same holds true for organisational transformation.

The skill is not in designing the change. It is in reading the room long enough to let it land.