Digital Transformation - Good Intentions, Big Hopes, and the Endless Depths of Hearsay, Broken Levers, and Failures to Launch

Digital transformation of legacy comes with formidable challenges. One could begin by citing the billions of dollars in overspends and the battle scars on CVs and careers that many consultants would use to instill fear and urgency in teams (simply Google “billion-dollar government projects” and you'll find numerous examples in any commonwealth government). However, I wanted to start with a more personal anecdote—one of my first experiences on the tumultuous side of digital transformation, for which no training or textbook could have adequately prepared me.

I was fortunate to join a small, high-performing transformation team. We had exceptional leaders, a diverse set of skills, and a deep understanding of the environment we aimed to change. Our mission wasn't just to meet expectations of what government could be, but to shatter them completely. Everyone in the organization shared this ambition, and the number of projects was too vast to count.

I felt ready. I had learned immensely from those around me, I knew the environment inside and out, and we had clear, decisive mandates for change. We had well-tested plans and execution frameworks, and I was eager to dive in and get started.

However, as I took on my first project with significant responsibility, the reality of driving these transformations hit me like a sledgehammer. Processes can only go so far in overcoming people and their perceptions, and the quote, “Everyone has a good plan until they get punched in the face,” became more of a mantra than an analogy. Suddenly, check-ins felt like interrogations. Hours were spent tracking down issues whispered in corridors and distorted through layers of communication before reaching steering committees. Suddenly, you were just one of those “project people.”

Interestingly, no individual or team had fundamentally changed their behavior or expectations from before the project started. It all came down to one glaring root cause:

People are Messy…

They are unpredictable, influenced by their perceptions, and will always prioritize their immediate selves and teams. Their experiences shape the culture, which in turn drives the project. The line between a failed and successful transformation is incredibly thin, and the challenges are not drastically different. I have worked on successful transformations that were far more draining than projects that never saw the light of day.

It’s easy to forget that we aren't just asking someone to use new software, follow a new process, or take on a new task. We are asking them to break a ritual, be trained in an unfamiliar way, follow a process they may not fully understand, and potentially take an ego hit by unlearning something they were previously confident in—or worse, replacing something they helped build or contribute to.

A person’s experiences are more than their interaction with a new software or process. While great UX is rightfully talked about more frequently, experiences don't happen in isolation. Real experience is far more complex than just user acceptance testing (yes, I've seen that passed off as UX). In fairness to project and implementation teams, gaining a deeper context is challenging when deploying to workforces of 1000+ people under intense time pressure.

This is why timelines can derail for the most unexpected reasons—reasons that no well-crafted risk management plan could anticipate. It’s these human experiences that lead to program directors being ambushed in steering committees and teams scrambling to chase shadows. Why does this happen? Emotions get involved, and it's incredibly hard to quantify or defend these issues with data.

So, You’re Telling Me People Are My Biggest Risk. How Do I Manage It?

First, ask yourself, “Is it my team’s job to manage everyone’s experiences?” The answer should be an emphatic NO! Program and project teams already have significant responsibilities, and expecting them to be fully skilled in change and people leadership is neither fair nor feasible.

So, if it's not the project team, then who is it? It's the people leading these employees every day. This creates a second dilemma: the addition of new technology, processes, or ways of working adds to their workload. This is often where transformation projects become perceived as the enemy of routine business.

This is where strong change management and communication become essential. Sadly, these are often left to overworked and under-resourced teams and individuals. Too often, change is treated as an afterthought rather than a prioritized capability, and experience measurement is relegated to a post-implementation review or a few listening roadshows.

Where to from Here?

Here are four key questions I challenge any great project/transformation team to ask themselves:

Examples of Successful Legacy Transformation

It’s not as simple as providing one perfect example of an amazing project or government department that has delivered a flawless digital transformation.

Understanding the contextual differences between environments is crucial when learning from others' successes. Core motivation should be the curiosity to see how we can improve. The examples I'm about to share occurred in their own specific contexts. A direct replication might not yield the same outcomes, but we can draw valuable lessons.

How the US Air Force Saw Challenges and Acted

One of the best examples of driving change through listening to the workforce is in an agency often perceived as traditional and resistant to change: the US Air Force.

Colt and his team treated warfighters and civilian staff as users, prioritizing their experiences during technology deployments and measuring them with the same KPIs used to understand customer satisfaction. They uncovered drivers of technology experience that directly impacted warfighter effectiveness. Terms like agility, speed, and reliability are now regularly used by Air Force leaders.

The key was gaining real-time experience insight, critical for a workforce undergoing constant systems modernization. Listening to the voices of 650,000+ people and integrating this qualitative data with incident response systems allowed for faster interventions. This wasn't just a single project approach but an enterprise-wide cultural shift.

How NSW Government Accepted Failure in Its Process to Modernize

I was fortunate to work in the NSW Department of Customer Service, considered a trailblazer in modern government. The pursuit of excellence was embedded in the culture. Servant leadership and engagement with senior leaders were normal. It was okay to fail fast and ask for help.

This led to massive transformations like digital licensing and a one-stop government shop. Top-down support was active engagement. Candor with impacted teams was a constant. Capturing experiences in data was a key business enabler.

Tried and True Methodologies Shouldn’t Be Left on PowerPoints and Papers

At Qualtrics, we work with partners to measure methodologies like ADKAR in the same way as CSAT, NPS, and Engagement. This focuses on performance, not just task completion. Work on training is similarly focused. Large changes require effective training, communication, and education. Measuring these gives early indications of potential issues.

How many methodologies are measured for effectiveness, not just task completion?

The New World of Benchmarking Change and Transformation

These are examples of teams that have delivered transformation well. Anyone whose work changes daily experience must take accountability for the whole environment that the technology will live in and not just the functions of a platform.

Central Government Programme activities

The techUK Central Government Programme provides a forum for government to engage with tech suppliers. We advocate for the govtech sector, evangelise tech as a solution to public sector challenges, facilitate market engagement, and help make the public sector an easier market to operate in. Visit the programme page here.