Why Digital Transformations Fail — And Why That Still Surprises Us

Digital transformation sounds great on paper—until you’re the one trying to lead it.

The promise is compelling: a connected technology stack, seamless data visibility, and insights that drive smarter decisions in real time. It's where every organization wants to be. If you are reading this article, then you are likely to have worked on a project that promises to solve all of your data problems or have tried to get your organization moving on one.  Yet, despite the effort and the money spent, very few get there. Most end up with somewhat improved systems and are able to transfer some of the manual work out of spreadsheets and into a digital platform. 

In nearly every organization I’ve worked with, digital transformation has been a top priority—discussed in boardrooms, strategy sessions, and operational planning meetings alike. But despite the urgency and investment, up to 70% of digital transformations fail to achieve their intended outcomes ( BCG ).

That figure isn’t just disappointing—it’s revealing.

What’s most concerning isn’t the failure rate itself, but the consistency with which the same issues appear. Time and again, I’ve seen familiar patterns emerge and stymie success even as organizations double down and try to get these massive projects over the finish line.

The good news is, these failure points are not without solutions. They are not mysteries to be cracked by a handful of experts.  They’re visible, preventable, and—most importantly— quite easily addressable problems.

In this post, I’ll walk through five of the most common reasons digital transformations falter, and why they remain so persistent across industries and initiatives.

The Five Common Failure Points

1. No Clear Strategy or Alignment

Too often, transformation is framed as a tech upgrade rather than a business imperative. This creates an unnatural division between business needs and system requirements from the beginning. Instead of a shared vision that can be thoughtfully implemented, each department pursues its own agenda and the result is a siloed, disconnected yet more expensive ecosystem. Without a common understanding of business needs across the organization—anchored to real strategic goals and metrics — efforts drift, duplicate, and eventually stall.

✅ Fix this: Define a business-led North Star. Tie every digital investment to a measurable business outcome.

2. Underinvestment in Change Management

The tech might be brilliant, but if people don’t adopt it, it won’t matter. And it’s not that people don’t want to adopt better technology and improve the day-to-day operations; they are not given sufficient time to do so effectively. Too often digital transformation is an annual review checklist item; the process is rushed and the final product pushed through to meet an arbitrary deadline. Instead of excitement, exhaustion sets it.   Change fatigue, lack of clarity, and fear of obsolescence will doom even the best intended implementations.

✅ Fix this: Prioritize change leadership as much as technical rollout. Equip managers to become active sponsors of change.

3. Gaps in Talent and Digital Capability

The pace of tech change is relentless and you can’t execute tomorrow’s vision with yesterday’s playbook. Still, many teams lack the digital fluency and systems thinking needed to translate transformation plans into sustained performance. Without the necessary know-how, your staff will feel disposable and disconnected from the project. It will be difficult or impossible to garner the enthusiasm no matter how attention grabbing your PowerPoint presentation might be.

✅ Fix this: Upskill where you can. Recruit where you must. Build digital muscle as a core capability—not an afterthought. Invest in your people alongside the investment in technology.

4. Poor Data Foundation

Here’s the unvarnished truth about digital transformation - you will need to spend a lot of time cleaning, organizing and aligning your data. No matter how advanced your analytics tools or how skilled your staff might be, garbage in still equals garbage out. Data that does not have a common system of organization, a single source of nomenclature, that does not anticipate business needs in its level of granularity will not deliver the business insights you are seeking no matter how much you spend on the digital platforms. Do not underestimate the level of granularity and the amount of time it will take to create a solid, trusted data foundation. 

✅ Fix this: Treat data as infrastructure. Invest in integration, governance, and accessibility before layering on intelligence.

5. No Quick Wins = No Momentum

Your digital transformation will be a journey; more of a marathon than a sprint. The pace of that journey is not going to be even. Sometimes you will need to speed up and at other times, you will need to slow down. The level of dedication required from your staff will be high and transformation fatigue will become real. At the same time, long timelines without visible results will cause stakeholders to disengage and budgets to dry up.

✅ Fix this: Sequence early wins to win support and sustain investment. Prove value fast through easily achievable milestones. Then, use this success to build support for deeper transformation.

The Takeaway 

Digital transformation is no longer optional.  It is a core part of the operating foundation of a well functioning organization today. But implementing it successfully in any organization is far from guaranteed. The good news? These problems you are likely to face are not unique or insurmountable. With the right focus, leadership, and design, transformation becomes not just possible, but repeatable.  Success becomes ingrained in every part of the journey and the result is worth the effort and the money spent.