Digital Transformation Strategy: A Night of Insights from Industry Experts

There is a whakatauki (proverb) that describes transformation beautifully: "As one fern frond dies, another rises to take its place." At Digital Garage, we understand that digital transformation projects are key drivers of change across industries. At some point, every organisation will face the need for a major upgrade or renewal in the face of changing customer demands or simply new and better tech coming along.

Digital transformation strategy is so important to get right that we thought it would be a good idea to host a discussion with a few seasoned professionals in the digital transformation space. Here are the highlights from the forum, hosted by our director, Jamie Blackwell and presented here as food for thought.

Big Bang vs. Iterative?

Digital transformation projects usually start with a defined methodology, either a 'big bang' approach, where changes occur simultaneously, or an iterative, agile approach, where smaller, incremental steps are taken over time. One of the key questions we asked our expert panellists was how they decide between the two.

Paul Munro, who leads a Product Engineering team for a multinational payments business, explained that both big bang and iterative approaches have their pros and cons. The Big Bang approach is often necessary for overhauling core systems and enabling future agility. This approach allows companies to re-baseline their tech infrastructure, so future changes can be implemented without substantial additional costs. However, in rapidly changing industries, the ideal position tends to be iterative. The Big Bang approach requires more careful upfront planning, as well as an awareness of potential challenges and risks.

Karlene Uelese, previously a transformation program manager at a training and workforce development organisation, noted that a Big Bang approach works well for high-stakes initiatives, such as aligning with major government reforms before a significant data migration. In these cases, every element was carefully planned, tested, and launched simultaneously to meet a critical deadline that couldn't be missed.

For less time-sensitive projects, however, she found that an agile approach allowed her teams to incorporate feedback iteratively, improving solutions while minimising disruption.

Communication is Critical

Throughout the discussion, a key theme surfaced repeatedly: the importance of clear and consistent communication. "Early and often" is best, especially for far-reaching transformations that affect all areas of an organisation.

Avoiding communication gaps is essential. Sharing updates about no changes is better than no updates at all. When there is prolonged silence, stakeholders might start drawing their own conclusions, which can lead to all sorts of problems.

A sound communication strategy fosters team engagement and builds a shared understanding of project objectives. When stakeholders understand the purpose behind each change, they're more likely to feel invested in the outcome and contribute constructively. Everyone needs to understand why they've been asked to come along for the ride.

Will Palmer, a co-founder and CEO of DevRamp, illustrated his experience with communication challenges when leading dev teams. Getting everyone on board, he said, "was about understanding the 'why' behind each decision." For Will, this meant spending time with key players individually, addressing their concerns, and ensuring they felt heard before moving forward with a large-scale announcement. By building consensus in smaller groups, he was able to create a critical mass of support - which made it easier to win over the remaining team members.

Karlene Uelese added that the level of leadership involvement is a deciding factor in successful transformation. Without leadership buy-in, a standalone transformation team cannot accomplish its goals effectively. By helping team members see "what's in it for me," she added, it's easier to build a shared sense of purpose and direction that keeps teams motivated throughout the process. "When you keep people informed, you keep the energy up."

How to Keep Momentum Going

Sustaining momentum in digital transformation projects involves more than just setting a course. Mark Daniels, a CTO on our panel, spoke about this point, saying that leaders must provide reassurance, not just direction. The journey won't be smooth, and there will be obstacles, he said, but with engagement, "we can keep the goal in mind."

Will Palmer also shared a personal lesson on the pitfalls of distraction. Reflecting on his time as a CEO, he recounted a situation where introducing new ideas mid-project led to confusion and actually derailed progress. This, he admitted, affected the team's morale.

The lesson from that experience, he said, was to recognise that protecting teams from distractions - whether internal or external - is just as crucial as coming up with new ideas. It's the leader's role to "prevent competing priorities from getting in the way" of the team, he said.

Our panel also highlighted the importance of removing obstacles for teams engaged in projects. The obstacles could be anything from adequate staffing, funding, or managing competing other priorities, but it's leaders who must recognise these roadblocks and work to eliminate them. That's the best way to keep momentum going and prevent teams from getting bogged down by unforeseen challenges.

Tapping into Data for Decision-Making

Analytics helps leaders assess progress and adjust strategies, the panellists agreed. Speaking from his point of view as a CTO, Mark Daniels said real-time data metrics give early indications a project is veering off course. "Managing project risk around data is really important."

Whether it's targets for revenue, cost optimisation, human capital investment, or technical metrics, weighing up that data against project results is essential for making the right impact, he said.

Data collection, Will Palmer added, can take many forms - whether through user engagement metrics, qualitative feedback, or A/B testing. His own startup tracks every interaction within its platform, gaining insights into customer preferences before pouring more resources into a project.

In start-up environments, the MVP approach allows organisations to make smaller and incremental changes, testing assumptions fully with multiple data points, before going all-in with resource investment. This ethos, Palmer argued, could benefit organisations of all sizes, not just startups.

If businesses prioritised learning through small experiments, they would be able to truly validate projects before they fully get off the ground, said Palmer. In other words, organisations would create less waste and have more purposeful transformations.

Defining Success Beyond Financial Metrics

Financial outcomes are often the primary focus of digital transformation projects - but the speakers agreed that true success involves more than just profitability.

Compliance and security are critical drivers, particularly as regulations evolve and cyber threats grow more sophisticated. Systems get old and need updating simply to stay viable.

Nurturing Project Advocates

Speaking of his experience in a previous business, Paul Munro said it's crucial to establish a change advocate who can pass on the baton when an external consultant ends their engagement. "There's got to be a leader who takes over at that point."

As a consultant herself, Karlene Uelese said she works closely with managers to ensure the ball isn't dropped when she ends her involvement with a project. Organisations benefit from embedding knowledge gained from external consultants and developing it further in-house. If that knowledge doesn't stick, it's going to fail - "we've seen that time and time again."

The Golden Nugget

So, what's the key takeaway from this discussion, the golden nugget of wisdom? The answer is "it depends"... Jokes aside, it's clear that organisations must be able to anticipate a wide range of human and material factors when planning a transformation. The path forward might not always be clear, but adding enough flexibility into project planning upfront often helps companies avoid unpleasant surprises.

Whether through a bold, big-bang approach or a cautious, iterative one, the success of any transformation lies in the ability to adapt, communicate and engage.

This journey, as all agreed, isn't easy. Yet by empowering your teams, prioritising learning, and banding together on a shared vision, you can build a transformative culture where innovation is the default.

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