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Why Do Digital Transformations Usually Fail, and What Corporate Leaders Can Do to Prevent It (Post-COVID Era Update)

Updated: Apr 16

Digital transformation is not a luxury but a drive for survival for the rest of the century. However, the process is fraught with challenges, and a significant number of these initiatives fail.

One of my clients recently said, “We spent a lot of money on DX, but users cannot use those new systems due to UI issues, bugs, or some of their processes are still in manual and on paper. We didn’t do a good job!”

Understanding the reasons behind these failures and how to prevent them, especially in a post-COVID world, is crucial for corporate leaders.

Common Reasons for Failure in Digital Transformation

  1. Lack of Clear Strategy and Vision Digital transformations often fail due to the absence of a clear, compelling vision. Without a strategic direction, initiatives can become disjointed. Organizations may adopt new technologies without understanding how they contribute to the overall business goals.

  2. Resistance to Change Resistance from both employees and management can significantly impede the adoption of new technologies and processes. This resistance often stems from a fear of the unknown and a lack of commitment, exacerbated by the challenges of remote and hybrid work models introduced during the pandemic. Inertia and resistance to change is natural because it takes energy and it is risky. It is particularly tricky in Japan, where the culture, generally speaking, one of the most risk averse ones in the world. The reasons for not changing things are usually rationalized due to potential customer objections or risk of errors.

  3. Inadequate Leadership Effective leadership is crucial in driving digital transformation. Failures often occur when leaders do not show full commitment or when they fail to lead by example, resulting in insufficient resource allocation and a lack of motivation among team members. Leadership across all levels, not only at top, is badly needed in companies where working in silos and verticals have been the norm. We see this usually in Japan, where "us" is usually someone's immediate team. The leaders should redefine "us" and make sure there is a sense of urgency and mutual benefit in creating camaraderie.

  4. Poor Integration of New Technologies For digital transformation to succeed, new technologies must be effectively integrated with existing systems. Poor integration can lead to operational disruptions and diminish the potential benefits of digital initiatives.

  5. Neglecting Sustainability and Stakeholder Feedback Ignoring sustainability goals or failing to incorporate stakeholder (customers and employees) feedback can lead to a misalignment between transformation objectives and actual user needs. This oversight has become increasingly problematic as consumer and regulatory demands for eco-friendly practices have grown.

Strategies for Successful Digital Transformation

  1. Establish a Clear Vision and Strategy Corporate leaders must articulate a clear vision that aligns digital transformation with the organization’s overall objectives. This strategy should address not only technological adoption but also how these tools will facilitate flexible work arrangements and enhance operational sustainability. The vision and the reason for change have to be clear and has to be shared with the leaders and employees of customers and suppliers as well. In one of the workshops I ran on “Digital Leadership,” the participants were debating how to influence their agents for DX. They were worried that those agents wouldn’t agree with the benefits and would focus on short-term cost impacts.

  2. Foster a Culture of Change and Innovation Leaders should work to create an organizational culture that embraces change and innovation. This includes providing training and resources to help employees adapt to new technologies and processes, particularly in a remote or hybrid setting. Especially in Japan, the case for change has to be very clear and has to consider both short and long term perspectives. Sometimes, it can be about customer satisfaction, which is extremely important in Japan. Sometimes, it is all about “fear of losing out” to competition. The best one could be to see an opportunity for taking a lead in competition. Again in Japan, the middle managers, who are only a few years away from their retirement might be reluctant to take any risks in the final years of their career. In such cases, the organization has to make sure that “there is something in it” for those managers as well. This is where coaching will help to create a personal narrative of change. If nothing works and those managers keep becoming bottlenecks in change, some hard decisions need to be made. In Japan, you cannot (easily) let go of people, but you can change their positions without causing them to lose face and salaries.

  3. Lead by Example Leaders must demonstrate their commitment to the digital transformation through active involvement and by adapting to new technologies themselves. This visible leadership helps inspire confidence and motivates employees throughout the organization.

  4. Ensure Seamless Technology Integration Seamless integration of new technologies with existing systems is essential. This requires careful planning, testing, and support to ensure operational continuity and to leverage the full capabilities of new digital tools.

  5. Prioritize Continuous Engagement and Feedback Regularly soliciting and addressing feedback from both customers and employees is vital. Leaders should establish mechanisms to capture this feedback effectively and use it to make ongoing adjustments to the transformation strategy, thereby ensuring alignment with user needs and sustainability objectives.

  6. Embrace Sustainable Practices Integrating sustainability into digital transformation strategies is not only about compliance but also about leveraging digital technologies to achieve more efficient and environmentally friendly operations. Leaders should ensure that their digital initiatives help reduce the organization's carbon footprint and promote sustainable business practices.


Digital transformation is a complex process that requires a comprehensive and strategic approach, particularly in the evolving post-COVID landscape. By addressing key areas such as strategic alignment, cultural adaptation, leadership, integration, and sustainability, corporate leaders can significantly increase the likelihood of successful transformation.

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