Not another ’why do digital transformation projects fail’ blog 

I know… you’ve probably read a hundred articles trying to arm yourself with the “do’s and don’ts” before kicking off your own digital transformation. Here’s a quick checklist — give yourself a point for every one you’ve seen before, and two if you’ve actually lived it. 

Strategy and Vision: Did you jump in with technology before fully thinking through the strategy? 

Leadership and Governance: Your change matters to you, but does anyone else in the organization care? And more importantly, do you need them to? 

Change and Cultural Resistance: Tried this before and it flopped? Consultants swoop in but miss what really happens on the ground? People left in the dark about how it affects them? And now no one’s getting on board? 

Skills and Talent Shortage: New tools mean new skills. Not enough time for training, not enough familiarity, not enough expertise to drive adoption. Sound familiar? 

Silos Everywhere: Did you forget who owns the data you need? Underestimate integration costs? Overlook the impact on other teams? 

Technology Over People and Process: AI will fix it, right? Automating the same processes you already have can just make the same mess faster. 

Data: BI tools, back-end systems, dashboards — yet still no consistency. 

Time and Money: What corners were cut? Why was the investment only for the initial transformation and not the ongoing journey? 

Success Metrics: You might track trailing metrics, but what about leading indicators like adoption and KPIs? Or long-term impact? 

The “Other” Stuff: Suppliers didn’t deliver as expected, or priorities shifted mid-project. Why is change always moving? 

For the record, if I score the transformation projects I’ve been involved with over the years… I hit 20 points. 

But this blog isn’t about strategies for fixing the above. They’re just listed as a reminder of the roadblocks we all end up navigating, and I’m sure a quick AI search will give you what looks like a credible set of plans and actions to remediate any of them. 

So why do I mention them at all, you ask? 

Well, I thought you might find it interesting – if not valuable – to understand some common themes that span several companies that I engage with, and how they’re taking a pragmatic approach to handling some of these pitfalls. 

A little background on my standpoint, and full disclosure. I work for Cyferd, a company built to help organizations rapidly deploy custom applications using a cloud-based development and deployment platform, unified data model, powerful workflows and integrations, enterprise-level visualization and embedded AI capabilities. So little wonder that the companies I speak with are all looking to innovate, modernize and digitize their existing digital portfolio.  

Business Engagement 

The first common theme I see across these companies is that I’m almost always speaking directly with the business stakeholders who want the benefits. Sometimes they bring their IT partners along, but far more often IT only gets involved after we’ve proven we can deliver the outcomes the business is looking for. 

The IT team asks us all the usual questions around security, business continuity, certifications (yada yada!), but those only get addressed once it’s worth everyone’s time—by then there’s usually business sponsorship in place to fast-track the process. 

We usually meet these business leaders through introductions, referrals, or at industry events (theirs, not ours). They tend to be a particular type: highly knowledgeable about the tools and processes that support their part of the business. They’re innovators, thought leaders, and budget holders, with a sharp understanding of both the strengths and the limitations of their current technology choices. 

They even typically have a pretty good idea of how AI-based assists could help them to accelerate. By the time I meet them, they’ve typically already assessed what shrink-wrapped solutions are out there that can meet their needs. Basically, they’re annoyingly smart, well-informed and curious! 

It’s not what you do, it’s how you do it 

When I first started having these conversations, I expected people to want to dive straight into the details of specific apps, whether those were things we had built or solutions from our partners. And to be fair, that is often where the conversations began. 

At procurement and supply chain events, the hot topics were sourcing automation, autonomy, and getting indirect spend under control. In legal, it was all about case and document management. In insurance, it was industrializing processes across syndicates, brokerages, and claims authorities. 

So yes, the entry point was usually an industry-specific solution. We built plenty of opportunities around that. But the most forward-thinking leaders, the ones I mentioned earlier, almost always shifted the conversation. Instead of staying focused on the app, they wanted to know about the platform behind it: integrations, conditional workflows, deployment speed, AI leverage. 

That is when the lightbulb moment hits. 

What they realized was that our platform could be applied across multiple use cases in their business without ripping out the investments they had already made. For them, that meant they could justify a single department-sized solution on its own budget, while also creating a launchpad for future applications. Those new apps could then reuse the same data and integrations, giving different teams a consistent “look and feel” while cutting out duplication. 

Of course, that’s exactly the conclusion we wanted – we’re a platform, after all – but we honestly didn’t expect them to evaluate us like that.  

What we learned in return was just as important: nobody really cares about “a platform”, what they care about is solving an immediate, real-world, industry problem. Once we show we can do that, then they are ready to see the bigger picture, the economies and repeatability that come from applying those same capabilities to other parts of the business. 

And the best part? We realized just how reusable our building blocks were in the real world. Approval workflows, privilege management across SSO, HR, and directory services, combining spreadsheet inputs with system data, AI-driven workflows that create and enhance text outputs – turns out these underpinnings were common across loads of use cases. 

Are you a hammer looking for a nail? 

“If the only tool you have is a hammer, you tend to see every problem as a nail.”  
Abraham Maslow (yes, the same Maslow who designed the hierarchy of needs J) 

How many systems have you seen stretched to handle “related” tasks, only for them not to quite fit? Over the years I’ve seen some eye-watering extensions of ERPs, service desk tools, and core business systems. 

The risk is that requirements change, and those extensions quickly become expensive and painful to maintain. But with so much money and effort already sunk in, you are forced to “sweat the asset” before even considering a change. 

Add in preferred supplier lists and catalog structures, and suddenly your transformation project is carved up according to the limits of whatever tech is already in place. 

In conversations with leaders, it’s clear they understand that a digital transformation is only as strong as its weakest link. They’ve already worked out whether it’s viable to stretch their existing systems into the gaps. If it isn’t, they’ve likely spoken to internal or external dev teams about custom builds (which is a bit like trying to make every problem look like a nail). 

After speaking with us, the situation changes. The message we hear is: “We love what you do and how you do it. Now we need to find the right problem for you to solve.” 

Traditionally, in software sales, this would be the moment you start questioning your career choices. It’s the equivalent of hearing: “It’s not you, it’s me.” 

But that’s not what we’re seeing. 

These leaders really do go back, sift through their innovation backlog and budgets, and find an appropriate landing point. They identify a use case with business sponsorship, allocated budget, and a clear role as a milestone in their wider transformation journey. 

Real-World Wins 

Here’s an example of how these situations often play out. 

We got the “it’s not you, it’s me” message. Then came the callback: they’d found a match. 

They were considering not renewing their employee communications system. Instead, they realized they could build an app on our platform that reused the employee security model and approval processes already in place across multiple backlog applications. 

Their budget came from redirecting the renewal spend. They also needed to address challenges in the legacy system to deliver improvements there. When they pulled the full costing together, they weighed the higher year-one development cost against reduced spend in years two and three. The result was a net saving even within the new-and-improved Employee Comms app. 

From there, they could extrapolate the savings across the next four projects, all of which relied on the same employee and organizational data. They gained further savings by only certifying data once for use across all projects, by hosting it on the cloud platform, and by avoiding repeated contracting and legal overhead through upfront software and services agreements. 

Another example: we were invited to propose a solution to bring indirect spend under control across thousands of stores for a large retailer. This wasn’t about replacing a legacy system but fitting neatly between their request system and procurement system. We built a request categorization and approval layer that pulled in organizational, budgetary, and ERP data before routing to procurement. 

We built a proof-of-concept and made strong progress—until we heard the dreaded words: “We’re going through a reduction in force; your project is cancelled until we’re through it.” 

We thought that was the end of it. 

We were wrong. 

One of the people affected by the RIF was an innovation leader. Soon after, he took up a leadership role in another team. After 30 days of discovery, he stopped one of his ongoing innovation projects because it didn’t create the baseline for future savings he had seen in our earlier engagement. Instead, he picked up the phone and called us. 

Key Takeaways 

A few key threads stand out that go beyond the traditional reasons I mentioned at the start of this blog: 

• Review your renewals — they might be the perfect landing point for transformation. 

• Keep an innovation backlog and a budget if you want any real shot at digital transformation. 

• Map the dependencies between innovation projects and your existing systems. 

• Start small, but choose projects that are strategic enough to justify their own budget. 

• Identify where AI can improve process intake or enhance outputs. 

• Explore innovations at your industry trade events, even if they don’t seem to tackle your immediate challenges. 

Best of luck, I hope these thoughts give you a start point of your plan for success