Get the first three moves right or risk everything

Starting a digital transformation?

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  • Insight
  • 10 minute read
  • 03/09/25

Digital transformation often comes with bold ambitions, big budgets and even bigger expectations. Yet, in many organisations, the early excitement fades when results don’t match the promise. The reality is that the initial phases – the ones often seen as preliminary or “just prep work” – are where success is built or lost.

Here are some lessons from transformation programmes across different industries, combined with insights from respected voices in the field.

Step 1 Be absolutely clear on why you’re doing this

In one large transformation, the leadership team kept referring to “digital transformation” as though it were a universally understood goal. It wasn’t. Early on, it became clear that the leadership team didn’t have a shared understanding of why the programme was being undertaken. When asked individually, each leader described a slightly different objective. That lack of alignment would have undermined the effort if left unresolved.

The goals for transformation can vary widely: top-line growth, new market entry, faster go-to-market, new product development, supply-chain optimisation, better data visibility, preparing for an IPO or enabling an M&A. Treating digital transformation as a one-size-fits-all solution is a costly mistake. Different goals demand different target operating models.

Sometimes, a full global “big-bang” roll-out is the right answer. Other times, a hybrid approach – sequenced by region, business unit or function – delivers better results, especially when process maturity is uneven.

One of the best ways to sharpen the case is to bring in an outside-in perspective – but always interpret it in the context of the organisation’s DNA, not an “ideal-world” model. Then build a solid business case, define clear milestones and KPIs and incorporate those KPIs into the LT’s own performance objectives.

When digital transformation is done right, it’s like a caterpillar turning into a butterfly; when done wrong, all you have is a really fast caterpillar.

George Westerman,MIT

Step 2 Don’t ignore change readiness – it’s where most fail

If there’s one question organisations should answer honestly, it’s this: Are we ready for the change we’re about to demand?

One consistent finding across programmes is that readiness for change is rarely uniform. In one programme, the push for change came from headquarters, driven by a global reporting need. But when the country-level teams were consulted, many were perfectly happy with their local systems. To them, the “improvement” looked like more work for less flexibility. Without careful preparation, this misalignment can lead to resistance.

Roadshows, interactive Q&A sessions and open forums can be powerful in building understanding and trust. In several cases, forming a network of change agents from different geographies and functions helped maintain momentum and created a two-way channel for feedback.

Simple but visible actions – programme branding, posters, newsletters and even small giveaways – can help the initiative feel tangible and present in daily work life. Most importantly, being transparent about the impact is critical: some roles will benefit, others will become more complex, and a few may be phased out. That honesty builds credibility.

People don’t resist change. They resist being changed

Peter Senge,Senior Lecturer of Behavioral and Policy Sciences, MIT

Step 3 Get the phasing right – resist the big-bang urge

It’s tempting to move from planning directly into full-scale implementation, but programmes that succeed often include a deliberate preparation phase.

In one multi-country programme, a couple of months were spent purely on Enterprise Architecture: aligning the business strategy with a technology roadmap, reviewing processes and systems across different markets and assessing organisational readiness. This revealed wide variations in how the same processes were run – some countries were at near world-class maturity, others were decades behind.

And here’s the key: don’t roll straight from prep into delivery. Pause, review findings with the leadership team, challenge assumptions, and, if needed, revise the entire roll-out strategy before a single system is touched. This pause can prevent what could become an expensive misstep and provides the time to design pilot phases that prove the concept before scaling.

Phasing might mean piloting in one market, rolling out by business unit or sequencing functions. Each phase should yield lessons that shape the next stage. The pressure to “just start building” is real – but giving in to it is often the fastest path to rework.

Vision without execution is hallucination — but execution without preparation is chaos.

Thomas Edison,American Inventor and Businessman

The CIO’s role: lead from the start, not the sidelines

The CIO function is uniquely positioned to bring all the moving parts of a transformation together. Unlike most functions, IT sits at the centre of the organisation, touching every business unit, process and geography. This vantage point enables the CIO to act as the orchestrator – ensuring that strategy, process, people and technology are aligned, dependencies are understood and risks are managed across the enterprise. Yet, in many transformations, CIOs are brought in after strategic decisions have already been set. By then, IT becomes the delivery arm rather than a strategic partner – and that’s a lost opportunity.

In the most successful programmes, the CIO is in the room from day one. They help shape the vision, bring a technology roadmap to the table and explain how technology can accelerate – or even help define – the business goals.

Before a transformation starts, CIOs should run a readiness project that includes:

  • Building an applications and systems catalogue
  • Assessing the health of the technology stack
  • Reviewing IT structure and skills
  • Mapping the technology roadmap
  • Cataloguing all active and planned IT projects

When the CIO enters the transformation with this baseline in hand, they can anticipate challenges, spot synergies and influence sequencing. More importantly, they position IT as a transformation driver, not just a service provider. This is critical because the orchestration role doesn’t end when the new technology goes live. The IT function must also be ready to operate and support the new technology construct that emerges from the transformation. This includes embedding the right capabilities, governance and service models so the organisation can sustain and evolve its new digital capabilities long after the initial programme is complete.

The CIO is no longer the head of technology – they are the conductor of the organisation’s digital orchestra.

Andi Mann,Digital Transformation Expert and Book Author

The hard truth

Technology may be the visible face of digital transformation, but the invisible foundations – clarity of strategy, readiness for change, thoughtful phasing and empowered CIO leadership – are what determine success.

Get these right, and you’ll have the traction, alignment and momentum to make the transformation stick. Miss them, and you risk building a very expensive, very fast caterpillar.

Contact us

Amit Singh

Director Technology & Data, Zurich, PwC Switzerland

+41 58 792 13 41

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