Kiandra Insights

Five reasons your digital transformation might fail

Cassie Wallace - Head of Software Development
by
Cassie Wallace
Head of Software Development
|
September 25, 2025
Cassie Wallace
Head of Software Development
September 25, 2025
Man sitting at a desk with a laptop, wearing glasses and a blue shirt, holding his face in frustration or exhaustion.

A digital transformation can be a career-defining moment for any leader. Organisations that adopt digitals olutions effectively, create the right mindset and embed new ways of working often deliver real change worthy of the name transformation.

But not all projects succeed. In fact, research shows that around 70% of digital transformation initiatives fall short of expectations. The result? Wasted time, investment and resources.

With more than $1 trillion being invested globally in digital transformation, this is an initiative you’ll want to get right.

So, how do you know if your project might fail? Here are the five most common reasons.

1. The mindset is not there

Digital transformation is not just an IT initiative. It’s a business-wide effort that touches every department and every employee.

One of the most common reasons digital projects fail is resistance to change. People worry about new systems, new processes or losing familiar ways of working. Without a positive mindset across the organisation, even the best technology won’t succeed.

Leaders need to build enthusiasm early. Show how the change will make people’s jobs easier, improve outcomes and help the organisation succeed. Work with executives and managers to share that vision so it spreads company-wide.

2. The wrong technology is chosen

It’s tempting to adopt the newest tool because it looks impressive. But shiny doesn’t always mean suitable. Choosing technology that doesn’t fit your business goals is like trying to build a skyscraper out of rubber – it won’t hold up.

Instead, select a technology stack that supports your strategy and scales with your needs. For example, if you need rapid deployment, low-code might be a good fit.If your business has highly specific requirements, custom software could deliver better long-term value.

The right technology, aligned to business outcomes, is critical for success.

3. No clear strategy

Ideas alone don’t drive transformation. Execution does.

Too often, projects begin without a clear roadmap. A strong digital transformation requires:

  • An assessment of business and user needs
  • Research into industry trends and competitor activity
  • Defined goals and measures of success
  • A realistic budget and resource plan
  • Training or recruitment for new skills.

Without this foundation, projects risk stalling or drifting away from their original objectives.

4. Lack of leadership alignment

Even when the mindset is positive, projects can fail if leadership is not aligned.If executives and managers are pulling in different directions, confusion spreads and progress slows.

Successful transformations require visible sponsorship from the CEO down, with leaders modelling commitment to the change. When leadership alignment is missing, the transformation becomes fragmented and loses momentum.

5. Underestimating culture and people

Digital transformation is as much about people as it is about technology. Ignoring company culture or failing to prepare staff for change is a major reason projects collapse.

Staff need support to adapt to new systems and processes. This might mean training, mentoring or simply giving people time to adjust. A culture that encourages learning and experimentation helps staff embrace change instead of resisting it.

Setting your transformation up for success

When executed well, digital transformation improves efficiency, boosts customer engagement, strengthens security and increases employee satisfaction. But success doesn’t happen by chance. It requires the right mindset, strategy, leadership, technology and culture.

If you’re ready to begin your next transformation, Kiandra can help set it up for success.

Talk to us today.

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