Credits: Chris Lawton

Why Most Digital Transformations Fail

Agron Fazliu
6 min readAug 23, 2024

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ARTICLE SERIES

Tech Realities Every Executive Must Hear: Insights from a Forthright Advisor

Digital transformation is an induced organizational change at unnatural speeds. Often, organizations cannot maintain this rapid pace and revert to their natural, slower rate of change, leading to what we call digital transformation failure. Most digital transformations fail due to unclear objectives, poor change management, technical debt, unrealistic expectations, and lack of executive support. Effective progress tracking, proper resource allocation, cultural alignment, and an iterative approach are crucial for success. Addressing these issues can significantly improve the chances of a successful digital transformation.

Digital transformations are often touted as the magic bullet that will catapult organizations into the future, promising increased efficiency, agility, and competitiveness. However, the stark reality is that most digital transformations fail.

If you’ve been involved in such initiatives, you know how frustrating and costly these failures can be. But why do so many digital transformations fall short? Understanding these pitfalls can help you navigate and mitigate them, ensuring your digital journey is a success. Let’s explore the causes of these failures and how to avoid them.

Lack of Clear Objectives

In my experience, setting specific, measurable, achievable, relevant, and time-bound (SMART) goals is crucial. For instance, instead of a vague goal like “improve customer experience,” aim for “reduce customer service response time by 50% within six months.” This clarity helps align your team’s efforts and provides a benchmark for measuring success.

One of the most significant reasons digital transformations fail is the absence of clear, well-defined objectives. Imagine embarking on a road trip without a destination in mind. You would waste time, resources, and energy driving aimlessly. The same principle applies to digital transformations. Without clear objectives, your transformation efforts can become disjointed and directionless.

Insufficient Change Management

Digital transformation is not just about implementing new technologies; it’s about changing the way your organization operates. This requires effective change management to ensure that your employees are on board and ready to adapt to new processes and systems. Unfortunately, many organizations overlook this aspect. We often observe that most, if not all, employees attend transformation workshops, but a month later, the outcomes are largely forgotten or not followed up on. What remains is the positive feeling and the collective desire to support change.

You need to communicate the vision and benefits of the transformation clearly and involve your employees in the process. Regular training sessions, workshops, and feedback mechanisms can facilitate smoother transitions. Remember, resistance to change is natural, but with proper change management, you can minimize its impact.

Many of us have witnessed situations where leadership and middle management are enthusiastic about change, while blue-collar employees continue their work, unaware of and unprepared for the first wave of change. This approach to digital transformation initially disrupts the organization, creating a wide division between upper management and the workforce, thereby greatly reducing the chances of long lasting success.

Underestimating Technical Debt

Technical debt accumulates when quick fixes are prioritized over long-term solutions. This can hinder your digital transformation efforts. Many organizations, in their rush to adopt new technologies, fail to address their existing technical debt, leading to integration issues, system failures, and increased costs.

Once, we agreed with the team to attempt calculating the technical debt based on IT engineers’ effort estimates for re-engineering the systems, resulting in 10 man-years of work. At this point, it became clear that patching systems to bypass the technical debt was futile, reinforcing the belief that digital transformation initiatives would be hard, slow, and painful if the organization did not address the technical debt as well.

Organizations need to conduct a thorough audit of current IT landscape before embarking on digital transformation journey. Address any existing technical debt and ensure that new systems are built on a solid foundation. This proactive approach will save significant time and resources in the long run.

Poor Progress Tracking

Tracking the progress of your digital transformation is essential to ensure that you are on the right path. However, organizations often lack effective progress tracking mechanisms, leading to missed deadlines and budget overruns.

Implement regular engaging discussions in addition to reports. Milestone reviews and performance metrics can help you stay on track and make necessary adjustments along the way. Transparency and accountability are key to successful progress tracking. The collective belief in transformation is the core value and pillar of digital transformation success.

Ignoring Cultural Change

Digital transformation is as much about changing the organizational culture as it is about technology. A culture that resists change can be a significant barrier to transformation efforts. If your employees are not willing to embrace new ways of working, your digital initiatives will likely fail.

Fostering a culture of innovation and continuous improvement is essential. Encourage your employees to experiment, learn from failures, and adapt to new technologies — all within business risk controls. Leadership plays a crucial role in this cultural shift. Lead by example and show your team that you are committed to the transformation.

Unrealistic Expectations

Many organizations embark on digital transformations with unrealistic expectations, believing that technology alone will solve all their problems. This leads to disappointment when the expected results are not achieved.

In many transformations, software refactoring is a key expectation. However, such transformation goals are often hugely influenced by business leaders rather than IT professionals, creating a significant divide between business/sales teams and product/development teams. This misalignment can result in transformation efforts causing more harm than good.

Set realistic expectations from the outset. Understand that digital transformation is a gradual process that requires time, effort, and resources. Be prepared for setbacks and challenges. Celebrate small wins along the way to keep the momentum going.

Lack of Executive Support

Executive support is critical for the success of any digital transformation initiative. Without strong leadership and commitment from the top, your transformation efforts can quickly lose momentum and direction.

Ensure that your executives are fully invested in the transformation. They should actively participate in planning, decision-making, and communicating the vision to the rest of the organization. Executive support provides the necessary authority and resources to drive the transformation forward.

Inadequate Resource Allocation

Digital transformations require significant investment in terms of time, money, and human resources. However, many organizations underestimate the resources needed and fail to allocate them appropriately.

Conduct a thorough resource assessment and ensure that you have the necessary budget, talent, and technology to support your transformation efforts. This includes investing in the right tools, training your employees, and possibly hiring new talent with the required skills and expertise.

One of the critical mistakes in digital transformation is hiring one or two external experts and relying solely on their contributions to drive the entire transformation. Instead, this process should be led by organizational leadership, with support and alignment from the entire organization.

Misaligned Incentives

If the incentives of your employees and teams are not aligned with your transformation goals, achieving success can be challenging. For instance, if your sales team is still incentivized based on traditional sales metrics, they may not be motivated to adopt new digital sales tools. Similarly, even if your products are highly competitive, relying solely on a salary-based sales model turns growth into a mere hopeful aspiration.

Align your incentives with your transformation objectives. Review and adjust your performance metrics, reward systems, and KPIs to ensure that they support your digital initiatives. This alignment will motivate your employees to embrace the transformation and work towards its success.

Failure to Iterate

Digital transformation is not a one-time project but an ongoing journey. Many organizations fail to recognize this, treating it as a one-off initiative, which leads to stagnation and missed opportunities. In these cases, blame often falls on external experts and subsequently fades away, while the organization reverts to its usual evolutionary processes.

Adopt an iterative approach to digital transformation. Continuously assess and refine your strategies based on feedback and performance metrics. Stay agile and be willing to pivot when necessary. This iterative mindset will help you stay ahead of the curve and continuously improve your digital capabilities.

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Digital transformations are complex and challenging, but they are also essential for staying competitive in today’s fast-paced business environment. By understanding the common pitfalls and proactively addressing them, you can significantly increase your chances of success.

As you embark on your digital transformation journey, remember to set clear objectives, invest in change management, address technical debt, track progress diligently, foster a culture of innovation, set realistic expectations, secure executive support, allocate resources appropriately, align incentives, and adopt an iterative approach. With these strategies in place, you’ll be well-equipped to navigate the challenges and achieve your digital transformation goals.

If this sounds familiar and you’d like to share your story, I’d love to hear from you.

ARTICLE SERIES

Tech Realities Every Executive Must Hear: Insights from a Forthright Advisor

  1. AI: The Misunderstood Threat to Your Business
  2. Why Most Digital Transformations Fail
  3. The Hidden Costs of Legacy IT Systems
  4. Misaligned IT and Business Goals
  5. Why do IT leaders prefer external hires?

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Agron Fazliu
Agron Fazliu

Written by Agron Fazliu

Chief Information Officer (CIO) | Co-founder

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