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10 Reasons Why Digital Transformation Fails

Summary: The article examines the reasons behind the failure of digital transformation initiatives, including the absence of clear strategies, resistance to change, inadequate leadership, and organizational challenges. Real-world examples are used to illustrate these issues, providing insights for organizations undertaking digital transformation endeavors.


"Despite the enormous pressure to stay ahead of the competition, more than 80% of digital transformations across the globe fail."

Digital transformation initiatives can fail for various reasons, and understanding these challenges is crucial for organizations embarking on their transformation journeys. In this article, we will explore 10 common reasons behind failed digital transformation initiatives, accompanied by business case examples that Vanaya Indonesia has curated. By examining real-world scenarios, we can gain insights into the pitfalls and obstacles that organizations have encountered along the way.

Table of Contents:

1. Lack of Clear Strategy and Vision

2. Resistance to Change from Internal

3. Inadequate Leadership to See Digital Potential

4. Siloed Organizational Structure

5. Legacy Systems and Technical Debt

6. Lack of customer-centricity

7. Cybersecurity and data privacy concerns

8. Insufficient Scalability and Integration

9. Lack of continuous monitoring and adaptation

10. Lack of Data-Driven Decision Making

1. Lack of Clear Strategy and Vision

Image source: The Editors Club

Without a well-defined strategy and vision, digital transformation efforts can become fragmented and lack direction. Let's take a look at the case of Debenhams, a British retailer that went bankrupt and closed in 2020 because it didn't adjust to changes in how people shop and didn't embrace online sales. Debenhams was known for its evening wear department, which was popular among middle-class customers for important events. Despite trying to restructure for a year, the 243-year-old store failed to find a buyer and had to shut down.

This situation shows the common challenge faced by traditional physical retailers when trying to adapt to online shopping and competing with fast-fashion companies. Since February 2020, online clothing sales in Britain have grown by 17 percent, while in-store sales have dropped by 22 percent. Foreign fast-fashion giants like Zara from Spain and H&M from Sweden started offering cheaper and trendier clothes. They were followed by online-only startups like Boohoo and Pretty Little Thing, which catered to young women and used social media to sell low-priced fashion products.

Older retailers and department stores that didn't invest quickly enough in online operations now struggle with the costs of maintaining large physical stores that fewer people visit.

2. Resistance to Change from Internal

Image source: Behance

Resistance from employees, especially at the leadership level, can hinder the successful implementation of digital transformation. Kodak's failure to embrace digital photography despite inventing the digital camera technology is a well-known example of resistance to change.

Kodak's failure can be attributed to various factors, including resistance from employees, particularly at the leadership level, to embrace digital transformation. Despite being the pioneer in digital camera technology, Kodak struggled to adapt and capitalize on the emerging digital photography market, ultimately leading to its downfall.

One significant aspect that impeded Kodak's successful implementation of digital transformation was internal resistance. Employees, including key leaders within the organization, were resistant to change and hesitant to fully embrace digital technologies. This resistance stemmed from a combination of factors, such as a fear of disrupting the existing film-based business model, concerns about the potential impact on traditional revenue streams, and a reluctance to deviate from established practices.

"When George Eastman (Founder of Kodak) passed away, his significant influence on the company created a strong sense of nostalgia within Kodak," explained Nancy West, a professor at the University of Missouri who extensively studied the early years of Kodak. She emphasized that while nostalgia may evoke positive sentiments, it also acts as a barrier to moving forward.

3. Inadequate Leadership to See Digital Potential

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Digital transformation requires strong and visionary leadership. Blockbuster's inability to compete with Netflix can be attributed, in part, to the lack of leadership that fully understood the potential of digital technologies.

When he had already established his business, Reed Hastings (Co-Founder of Netflix), believed that Blockbuster and Netflix should put aside their rivalry and form a strategic alliance to strengthen the market , given its significance in the industry. However, Antioco, the CEO of Blockbuster at the time, did not view it as a favorable proposition and rejected the idea.

Despite Blockbuster having the necessary resources to enter this business, they deemed it more profitable to maintain their existing model instead of follwing Netflix's approach in offering its DVD rental service through email and streaming. Consequently, Blockbuster missed out on a golden opportunity by resisting change.

Around one year after this proposal, video rentals became obsolete in the United States, and eventually, in the rest of the world. In the subsequent years, Blockbuster experienced a decline in its customer base due to the success of Netflix. Blockbuster's customers found Netflix's streaming service more appealing, prompting them to switch their allegiance.

4. Siloed Organizational Structure

Source: TRaiCE

Organizational silos can impede collaboration and hinder the integration of digital technologies across departments. Greensill Capital, a supply chain finance company, serves as a recent example of a company that faced significant challenges due to a siloed organizational structure.

The complexity of Greensill's organizational setup, with various subsidiaries operating independently, hindered transparency and risk management. This lack of integration and communication made it difficult to have a comprehensive view of the company's financial health and risk exposure. Greensill heavily relied on selling and securitizing invoices to generate funds, but the siloed structure resulted in inadequate oversight and control over its financing activities.

Compliance and regulatory obligations also posed difficulties, as different units operating in silos struggled to ensure consistent adherence to regulations and proper risk assessment. These issues led to setbacks, including the loss of major clients and increased regulatory scrutiny, culminating in Greensill's insolvency filing. Ultimately, the combination of a complex organizational structure, limited risk visibility, and compliance shortcomings contributed to the company's downfall.

5. Legacy Systems and Technical Debt

Image source: GHP News

The healthcare industry, like any other sector, faces challenges when it comes to implementing digital transformation. Outdated infrastructure, software, and limited resources can hinder the adoption of new digital technologies. Technical debt, accumulated from outdated or suboptimal technology, further complicates the process. These challenges stem from the complexity and interoperability issues associated with legacy systems, which use different technologies and lack standardized interfaces, making seamless integration difficult.

Replacing or upgrading these systems requires significant investments of time and resources. Resistance to change from healthcare professionals, who are accustomed to working with legacy systems, adds to the challenges. Moreover, concerns about data security and compliance with regulations raise additional complexities.

Overcoming these obstacles necessitates careful planning, stakeholder engagement, the establishment of interoperability standards, implementation of robust data security measures, and the gradual modernization of legacy systems. By addressing these challenges, the healthcare industry can unlock the potential of digital transformation to enhance patient care, streamline workflows, leverage data analytics, and drive innovation in healthcare delivery. Strategic investments in modernizing infrastructure and software are essential for long-term success in embracing digital technologies and improving healthcare outcomes.

6. Lack of customer-centricity

Image source: CTV News

Failing to prioritize customer needs and preferences can lead to digital transformation efforts that miss the mark. Sears, once a retail powerhouse, failed to adapt to changing customer expectations and the rise of e-commerce, ultimately leading to its bankruptcy in 2018.

One of the key reasons for Sears' downfall was its inability to evolve its business model to meet the demands of modern customers. As e-commerce gained traction, Sears failed to establish a strong online presence and neglected to invest adequately in digital strategies. This meant that the company missed out on capturing a significant portion of the growing online retail market.

Additionally, Sears faced challenges in providing a seamless and convenient shopping experience for customers. As consumer expectations shifted towards personalized and efficient service, the company struggled to deliver on these fronts. Other retailers, particularly online giants like Amazon, were quick to adapt to these changing demands and offered a wider range of products, competitive prices, and hassle-free shopping experiences.

Moreover, Sears had a vast physical footprint with many brick-and-mortar stores, which became a burden as consumer visit declined. The company was slow to respond to the changing retail landscape, where customers increasingly preferred the convenience of online shopping over visiting traditional stores.

7. Cybersecurity and data privacy concerns

Image Source: CNBC

Inadequate cybersecurity measures and data privacy issues can undermine trust and hinder digital transformation initiatives. The data breach incident faced by Colonial Pipeline in 2021 highlighted the importance of robust cybersecurity practices in digital infrastructure.

Colonial Pipeline is a major American oil pipeline system that transports petroleum products such as gasoline, diesel fuel, and jet fuel from refineries on the Gulf Coast to various destinations along the East Coast of the United States.

The data breach incident faced by Colonial Pipeline in 2021 was caused by a ransomware attack, where hackers gained unauthorized access to their systems. It started with a compromised password for an unused VPN account, allowing the attackers to exploit vulnerabilities in their legacy IT systems. As a result, Colonial Pipeline had to shut down its operations, leading to fuel shortages and disruptions in the southeastern United States.

This incident highlighted the vulnerability of critical infrastructure systems, the economic impact of cyberattacks, the interconnectedness of digital infrastructure, the rising threat of ransomware attacks, and the need for robust cybersecurity practices. It emphasized the importance of comprehensive security measures, modernizing legacy systems, multi-layered defenses, regular security audits, and employee awareness and training. The incident served as a reminder to organizations to be proactive in cybersecurity preparedness to protect digital infrastructure and minimize the potential impact of cyberattacks.

8. Insufficient Scalability and Integration

Image Source: PCMag

Digital transformation initiatives may fail if they lack the scalability and integration required to support growth and innovation. Quibi, a short-form mobile video platform launched in 2020, faced challenges due to its inability to gain traction and integrate with other platforms, ultimately resulting in its shutdown.

Timing worked against Quibi as it launched during the COVID-19 pandemic when people already had access to established streaming services. The market was saturated, making it difficult for Quibi to stand out. The platform struggled to differentiate its content from what was already available on other platforms.

Additionally, Quibi's limited integration with other platforms and devices hindered its growth potential. The subscription-based model and lack of a free, ad-supported option made it less appealing to users. Marketing efforts failed to effectively communicate Quibi's value proposition. Content challenges, including shows that didn't resonate with viewers, also impacted its success. Ultimately, these factors contributed to Quibi's inability to gain traction and its subsequent shutdown in December 2020, just months after its launch.

9. Lack of continuous monitoring and adaptation

Image Source: NPR

Digital transformation is an ongoing process that requires continuous monitoring and adaptation. The failure of General Electric (GE) to adapt to the digital revolution and capitalize on the opportunities presented by Industry 4.0 resulted in significant decline and restructuring efforts.

GE was slow to respond to the digital transformation and did not fully embrace the potential of digital technologies and data analytics. The company's legacy infrastructure, culture, and lack of agility hindered its ability to integrate new digital solutions. It was hard for GE to foster innovation and keep pace with more agile competitors. General Electric (GE) struggled with ineffective execution and integration of digital ventures, economic challenges, and leadership changes, which worsened the company's difficulties.

These factors led to a decline in performance and profitability, prompting GE to undertake restructuring efforts, divest non-core businesses, and refocus on core strengths. Despite ongoing efforts towards digital transformation, the delayed adaptation has had a lasting impact on GE's competitiveness.

10. Lack of Data-Driven Decision Making

Image source: USA Today

Barnes & Noble, a prominent bookstore chain, faced challenges in the digital era due to its limited adoption of data-driven decision making. The company struggled to leverage customer data effectively to tailor recommendations, optimize inventory management, and enhance the online shopping experience.

Unlike its competitor Amazon, which leveraged data analytics to offer personalized book recommendations and seamless online purchasing, Barnes & Noble fell behind in providing a personalized and customer-centric experience. The lack of data-driven decision making hindered the company's ability to anticipate market trends, allocate resources efficiently, and adapt to changing customer preferences. As a result, Barnes & Noble faced declining sales and store closures, underscoring the importance of data-driven insights for retailers in the digital age.

In conclusion, organizations embarking on digital transformation initiatives must address challenges such as the lack of clear strategy, resistance to change, inadequate leadership, siloed organizational structures, legacy systems, and insufficient scalability. They must also prioritize customer-centricity, cybersecurity, continuous monitoring, and data-driven decision making. Real-world examples above highlight the consequences of neglecting these factors. By learning from these failures and adopting a proactive and adaptive approach, organizations can increase their chances of successful digital transformation and thrive in the dynamic digital era.

Implementing agile leadership to drive innovation in the context of digital transformation can be a challenging endeavor. However, o gain a deeper understanding of the underlying principles, our program explores the scientific evidence supporting agile thinking development, digital leadership development, and creativity development. Visit Leading Digital with Agility to develop your digital capability.



  1. Reuters. (2012, January 19). Kodak files for bankruptcy.

  2. We Are Drew. (2021, May 7). How Kodak Failed (and How to Avoid the Same Fate) [Blog post].

  3. Deloitte. (2021, June 7). The Future of Risk in the Digital Era. Retrieved from [insert URL]

  4. Harvard Business Review. (2021, October 26). Digital Transformation Is Not About Technology.

  5. Reuters. (2021, January 19). Debenhams set to close all stores with 12,000 jobs lost.

  6. Rogers, B. (2016, January 7). Why 84% of Companies Fail at Digital Transformation. Forbes.

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