David Cox

Principal Consultant - Product Strategy
EE Life

July 8, 2025

Revealing the Good, the Bad and the Ugly of digital transformation

It’s almost impossible to work in digital technology without regularly hearing the word “transformation”. As a result, it’s easy to lose sight of what the term truly means for businesses and their delivery teams. Transformation is not simply another word for change. It describes a particular kind of change, one that is enduring, irreversible, and has far-reaching consequences.

In opening our latest Expert Talks event in Leeds, I invited a room full of technologists and transformation leaders to remember that transformation – a long-lasting and profound shift from one state to a radically different one – shouldn’t be taken lightly. Throughout the evening, we explored what transformation really means in practice: the cultural shifts, the emotional demands, the unpredictability, and the lasting consequences that come with it. Because real transformation isn’t a one-size-fits-all process or a checklist of deliverables, it’s a deep, and often uncomfortable, change that challenges assumptions, behaviours and ways of working.

With the right levels of understanding and emotional intelligence, it can lead to positive and lasting outcomes. Without them, it is often flawed from the start. Even with the best intentions, the complexities and challenges involved in digital transformation can cause things to unravel, which is why there is real value in sharing experiences with peers and learning from the lessons they reveal.

That was very much the format for Digital Transformation: The Good, the Bad and the Ugly on the 18th of June. It was an evening when clients from the public and private sector came together to talk through their successes and failures, and the lessons they’ve taken from them.

We were very fortunate to hear from two outstanding speakers: DEFRA’s Deputy Director for Digital Delivery, Richard Baines, and Lucy Auckland, Product Director for the multi-brand holiday business Awaze. Here’s what they and our other attendees had to say about the realities of digital transformation.

The Good: Human-centred transformation

The most successful transformation efforts begin with a recognition that change is rarely predictable. Each step forward reshapes the context for what comes next. These initiatives cannot be fully planned in advance, nor do they follow a simple, linear process. Success depends on the ability to adapt, which requires emotional intelligence, open-mindedness, and a focus on cultural change over purely technical delivery.

To support ongoing transformation, organisations need a culture that doesn’t attempt to predict the future but instead builds confidence in its ability to respond to change as it happens. This means creating safe environments where people can take risks and learn from the results. Richard Baines described the ideal transformation leader as someone with a strong IQ, emotional intelligence (EQ), and a low ego. Lucy Auckland highlighted the need for early, honest conversations about what transformation means for each team and function. Without this clarity, alignment quickly breaks down.

This approach reflects Equal Experts’ past collaboration with Pret A Manger, where agile development at scale was employed to rapidly grow digital capabilities during pandemic lockdowns. By focusing on user-centred design and iterative delivery, Pret introduced new digital propositions like coffee subscriptions and marketplace services that were focused on customer and business value and which acted as a foundation for future transformation. Read the case study.

The Bad: Dogmatic and overly determined

The flexible, evolving nature of transformation poses challenges when leaders try to stick rigidly to fixed plans or take on too many goals at once. Several attendees shared experiences of being pulled into overambitious programmes, often with multiple initiatives running in parallel. Others described the problems caused by failing to question whether every “must-have” truly added value.

Richard Baines shared his own experience of an early transformation project, when giving free rein to different ideas rapidly slowed down a team’s ability to deliver. Lucy Auckland warned of the importance of communicating in terms of business transformation rather than focusing just on technical delivery. It’s a crucial element in keeping transformations aligned to business strategies that can themselves evolve.

These are challenges we’ve encountered and worked through with clients. In one example, our collaboration with John Lewis & Partners involved modernising their digital platforms to enhance customer experience and operational efficiency. By focusing on iterative development and aligning technical delivery with business objectives, we helped them navigate the complexities of large-scale transformation. Read the full case study.

The Ugly: Learning the hard way to prioritise value and values

Our open forum highlighted how digital transformation can expose difficult realities when vision meets execution. Optimism and clarity of purpose are vital, but several speakers reflected on what happens when priorities are misjudged or people are overlooked.

A recurring theme was the risk of misjudging priorities, whether by chasing quick wins that lack lasting impact or by underestimating the toll that transformation can take on people and culture. Many participants reflected on the post-pandemic landscape, where the speed of change was celebrated, but the burnout and structural risks it caused were too easily forgotten.

Attendees also explored the tension between methodology and mindset, particularly in how Agile is applied. While Agile remains a cornerstone for many transformation strategies, there was a strong consensus that it must evolve, moving away from rigid interpretations and back toward its core principles of adaptability and responsiveness.

Ultimately, the most poignant insights revolved around the dual importance of delivering real business value and nurturing the human values that underpin successful change. The conversation reinforced a collective belief that the most effective transformation efforts are those that are intentional in both what they aim to achieve and how they go about achieving it, aligning commercial goals with cultural sustainability.

“If you succeed in delivering something but compromise your values, then that’s not a good outcome,” Richard Baines discussed. “Ultimately, it’s a better outcome not to deliver, but to maintain your integrity.”

When organisations approach transformation the right way, they ensure that their people maintain their resilience, their open-mindedness and their continued ability to change. After all, transformation isn’t something that happens once. In the right hands, it’s an organisational instinct that keeps delivering, and one that’s well worth building a culture around.

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