What I learned from a messy billion-dollar digital transformation

Approximately 70% of all digital transformation initiatives fail to meet their objectives. Often, that’s because organizations chase flashy new tech without fixing foundational issues. We learned this the hard way over three years, while embedded as a team of consultants-researchers in a nearly $1 billion digital overhaul at one of the world’s largest tourism companies. Instead of deploying AI or blockchain, our focus was on untangling decades-old systems and bridging siloed departments. It wasn’t glamorous, but it was transformational: Hugo Michou (senior consultant in Risks and Strategy, Deloitte Canada) and I shifted from a traditional supply chain mindset to a supply network approach, and how managing complexity, stakeholder alignment and governance ultimately saved the day.

Big plans, big challenges at a tourism giant

In 2015, a top executive at the company openly admitted that it was years behind in technology. That frank wake-up call set in motion a massive digital transformation program. The parent corporation had mandated a modernization across all subsidiaries, and local national leadership committed hundreds of millions of dollars to bring everything from procurement to inventory onto modern platforms. As the project lead, we soon discovered just how messy this “digital dream” would be in reality.

On paper, the plan was straightforward: replace legacy systems, standardize processes and integrate data across the enterprise. In practice, we were dealing with a 30-year-old organization that had accumulated layer upon layer of processes without ever revisiting underlying assumptions. As one colleague quipped, the company “had added a significant number of processes since its creation, but the way of thinking about these processes [had] not evolved,” leaving employees coping with obsolete methods (Michou & Richet, 2025a).

The purchasing system, for example, was a patchwork of homegrown tools and spreadsheets that different teams had tweaked for their own needs. Each department (parks, hotels, restaurants, retail) operated in its own bubble. Projects were often implemented in isolation; the benefits “only serve the interests of the team that carried it out,” leading to a multitude of disconnected solutions. We progressively identified these strategic misalignments between our technology investments and business needs.

The scale of operations added to the complexity. This tourism giant isn’t a single-site business: it’s an ecosystem. There were roughly 180 locations (theme park zones, hotels, restaurants, a shopping village) that needed daily supplies from the company’s own warehouses, external warehouses and many other suppliers. In other words, it wasn’t a simple linear supply chain at all, but a sprawling supply network of internal units and partners. And virtually every part of the organization was intertwined with this network: Changes in one area (say, hotel inventory or park entertainment schedules) could cascade into impacts on suppliers, warehouses and even customer experience. From day one, we were arguing to the top management team that the digital transformation was socio-technical, we were changing a living organism, not a machine.

The first major initiative, rolling out a new source-to-pay procurement platform, drove this point home. It wasn’t just an “IT project.” It affected six different departments at once, each with its own processes and priorities. Getting them onto one system meant surfacing long-standing conflicts (for example, between the finance team’s desire for strict controls and the operations team’s need for flexibility in sourcing). We had big plans to improve efficiency and visibility, but equally big challenges in getting everyone aligned.

The strategic pain points soon became clear: outdated systems that didn’t communicate, siloed departments protecting their own turf and structural misalignments where our subsidiary’s processes didn’t match the corporate standard (Michou and Richet, 2025b). We were, in effect, trying to rewire the plane while flying it.

From supply chain to supply network thinking

Early on, we made a subtle but essential shift in mindset: we stopped talking about “the supply chain” and started thinking in terms of the supply network. A traditional supply chain implies a linear sequence of steps focused largely on cost efficiency. That mindset had led our teams to optimize locally (each department squeezing its own costs) without seeing the bigger picture.

In reality, our supply network was a complex web of relationships (internal teams, suppliers, partners) all interconnected and constantly influencing each other. Even the phrase “supply network” reflects these nonlinear flows and webs of suppliers/customers in today’s operations. I witnessed exactly that: Information and goods flowed in multiple directions, and a hiccup in one node could disrupt many others.

Embracing this network perspective changed our approach. Instead of trying to simplify away the complexity, we set out to manage it effectively. We mapped out how orders, data and decisions moved across the company. The picture wasn’t pretty (think spaghetti diagram with dozens of feedback loops) but it was illuminating. For instance, we found that a delay in updating inventory data in the warehouse system would trickle into procurement (purchasers placing orders based on old data), which then impacted vendors downstream. These insights reinforced that we needed better coordination more than we needed fancy algorithms.

In fact, we learned that complexity isn’t always a bad thing; it’s a reality to be acknowledged. Our complex adaptive system of a supply network had many self-organizing parts. If we tried to force simplicity by ignoring those interdependencies, we’d create new problems. (One manager warned us not to “add bricks of complexity” on top of an already tangled environment, but to work on strengthening “the existing links between all members of the organization”.) So we shifted our focus to improving those links. We created cross-functional working groups to tackle each major process, ensuring representatives from all affected departments were in the loop. Instead of each team pulling in its own direction, we nudged everyone to pull together.

A vivid example of network thinking in action was how we addressed the disconnect between hotel operations and the rest of the company. Initially, the hotels managed guest bookings and supply needs almost independently; they weren’t “in the loop” with new product launches or park events that could spike demand. This lack of synchronized evolution between the hotels and other units led to some nasty surprises. For instance, stockouts of critical items on peak weekends happened because the hotel team didn’t know about a park promotion, a classic strategic misalignment. To fix this, we established new communication channels and integrated planning sessions, effectively weaving the hotels back into the broader supply network. We started treating internal units like part of the network, not isolated kingdoms.

We also looked at feedback loops within our system. Some loops were vicious cycles that fueled misalignment. For example, we saw that when stakeholder involvement was low during the design of a new process, the resulting solution didn’t meet their needs. That poor fit then caused those stakeholders to disengage further, leading to even lower involvement and worse outcomes: a textbook case of a vicious loop.

Our research into this transformation later confirmed this pattern: deficiencies like weak stakeholder engagement, outdated tech capabilities or structural issues tended to trigger misalignment, feeding back into further project troubles. Recognizing these dynamics, we took action to break the cycles. We made a rule that end-users would be involved at every stage of design and rollout, no exceptions. We also paused to upgrade some core infrastructure that was causing repeated failures, rather than plowing ahead on new features built over a shaky foundation. Bit by bit, we turned some of those vicious loops into virtuous ones, where early wins (like a smooth pilot deployment in one department) built confidence and led to greater stakeholder buy-in for the next phase.

Adopting a supply network mindset also meant redefining success. Instead of measuring each silo’s KPIs in isolation, we set shared metrics across the network (for instance, end-to-end order fulfillment time, which no single department could achieve alone). This encouraged collaboration because everyone’s performance was now tied to collective outcomes. In essence, we started behaving more like a network: more collaborative, adaptive and aware of interdependencies. It was a far cry from the old linear thinking, and it set the stage for the next element: bringing people along on the journey.

Aligning stakeholders and systems for co-evolution

The hardest part of this transformation wasn’t the technology; it was getting humans to work together in new ways. We learned that if the people and processes don’t evolve in sync with the new systems, the transformation will falter. In fact, roughly three-quarters of digital transformations fail to deliver ROI, and of those that fail, 70% are due to a lack of user adoption and behavioral change. Armed with that knowledge, we doubled down on stakeholder alignment and change management.

First, my colleague Hugo Michou took the lead in establishing a strong governance structure. A steering committee with executives from every major function (IT, operations, finance, merchandising, etc.) met bi-weekly to review progress and resolve disputes. This was not a perfunctory committee…it had teeth. If marketing and supply chain had a data-sharing issue, it got aired and addressed in these meetings rather than festering. The governance team’s mantra was “no blind spots.” By having all the stakeholders at the same table, we caught misalignments early. For example, when we discovered that a new inventory system feature might slow down front-line staff workflows, the operations lead flagged it and we adjusted the rollout plan on the spot. In the past, that kind of issue might only surface after full deployment (and lead to finger-pointing between IT and business). Governance gave us a forum to navigate complexity collectively.

Next, we focused on communication and culture. We knew from prior failed projects that sending a few emails about “new software coming, get ready” wouldn’t cut it. So we tried a more personal approach. We identified influential employees in each department (respected veterans, informal leaders) and recruited them as change champions. We shared with them not just what was changing, but why, and even showed them that messy “spaghetti” map to illustrate how their work fit into the bigger network. This transparency helped win allies. People started to see the transformation not as an IT dictate, but as a necessary evolution for the company’s survival and growth. One warehouse manager told us that seeing the full picture of the supply network made her realize the importance of standardizing processes: “We can’t master the whole value chain the same way as a simple chain…we need to understand our complex ecosystem, where all systems and agents communicate with each other.” Comments like that were a good sign: mindsets were shifting.

We also made training and co-evolution a centerpiece of the program. Co-evolution, in this context, means the technology and the organization adapting to each other over time. For instance, as our new procurement platform rolled out, we found we needed to reorganize teams and redefine roles to fully leverage it. We merged some purchasing and logistics teams under one process owner, which forced greater collaboration day-to-day.

We likewise updated job descriptions: Buyers were now expected to analyze data insights from the system, not just place orders, so we invested in upskilling them. Conversely, user feedback led us to tweak the software, such as adding a dashboard for hotel managers who needed a specific view of inventory that corporate hadn’t considered. This mutual adjustment between people and tech was messy, but it’s what ultimately delivered results. It reinforced a lesson: digital transformation is a journey of joint evolution between new tools and the people who use them.

Throughout the project, we consciously addressed two dimensions of change: the structural and the organizational (Michou & Richet, 2025a). Structural changes included org chart adjustments, governance frameworks and process redesign – essentially, the “hard” side of change. Organizational changes were the “soft” side: behaviors, norms, communication styles and skills.

Our academic research later highlighted that these two dimensions (structural and organizational) must be synchronized with the complexity of the network to avoid strategic misalignment (for more details, see Michou & Richet, 2025b). In practice, this meant whenever we introduced a new system or process (structural change), we paired it with workshops, coaching and sometimes even changes to incentive structures (organizational change) to encourage adoption. For example, when we rolled out a centralized supply planning process, we also adjusted the performance goals of local managers to include network-wide metrics instead of just local efficiency. If either side of that equation lagged, we risked creating a gap.

By the end of the three-year program, the company was far from perfect, but we had achieved a lot: A unified core system for procurement and inventory, clearer governance, better data visibility and departments that actually talked to each other. Perhaps more importantly, we fostered a new mindset that accepted complexity and emphasized continuous learning. The digital transformation wasn’t a one-and-done project; it became an ongoing capability of the organization. As a researcher-consultant, it was a challenging, sometimes chaotic ride. But it underscored that not all digital transformations are about glitzy technology – the unsexy work of fixing foundations and aligning people is what really drives success.

Key takeaways for CIOs

Every large-scale transformation is unique, but here are three practical lessons from my consulting experience and Digital Transformation research that may help fellow CIOs and digital leaders:

• Focus on foundations, not flash. It’s tempting to start with high-visibility tech like AI. Resist that urge. Modernizing core systems and processes (even if they’re old-school) often yields the biggest long-term gains. As we learned, adding a “flashy” digital tool on top of broken processes just creates more complexity without solving anything. Make sure your foundational capabilities are solid before layering on new tech.
• Bring people along (early and often). Technology doesn’t transform a business: its people do. Invest in change management from day one. Communicate the why behind changes, empower change champions and involve end-users in design and testing. Remember that lack of user adoption is behind roughly 70% of transformation failures. Create feedback loops with your teams so you can adjust and improve as you roll out new systems. Culture change is a marathon, not a sprint, so start aligning incentives and breaking silos as early as possible.
• Think in networks, not chains. Businesses today are interconnected systems, not linear chains. Encourage cross-functional and cross-company visibility. Map out how value actually flows through your organization (and partners) to identify bottlenecks and hidden interdependencies. This systems view will help you design a transformation that improves the whole, not just the parts. It also prepares you to be more resilient. Indeed, a truly resilient supply network aligns strategy, operations and governance so it can adapt quickly when conditions change. In practice, this means fostering collaboration and agility across departments and being ready to adapt plans when you discover new ripple effects.

Tackling complexity is never a smooth journey…but it pays off

Large-scale digital transformations can feel overwhelming and decidedly unglamorous. But as I saw firsthand, tackling the messy foundations pays off. Our tourism company went from a fragmented, outdated supply chain to a more adaptive supply network that’s ready for future innovation. The journey was anything but smooth (complexity never is!), yet that complexity holds the seeds of innovation if you learn to navigate it. For CIOs, the bottom line is this: Success isn’t about rolling out the fanciest new technology; it’s about enabling your organization to evolve alongside technology. Manage that co-evolution well, and even a “boring” transformation of core systems can unlock billion-dollar value for your business.

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