Why the Vast Majority of Digital Transformations Fail — And What to Do Differently

John Rossman

Digital transformation, the integration of digital technology into all areas of a business, is a fundamental re-thinking in how companies operate. Yet, according to a report by McKinsey, more than 70% of digital transformations fail. 

These failures could be due to various reasons, from lack of employee engagement to inadequate leadership. Let’s unpack these issues and provide solutions to lead a successful digital transformation.

Understanding Digital Transformation

Digital transformation isn’t merely about adopting more advanced technologies but about rethinking old operating models, fostering a culture of innovation, and driving profound change. It’s not just about digitizing for digitizing’s sake. It’s about creating more innovative processes and systems, increasing business agility, and driving better customer and employee experiences.

A time of turbulence is a dangerous time, but its greatest danger is a temptation to deny reality.” – Peter Drucker

The Importance of Digital Transformation

In our rapidly evolving digital age, being adaptable and innovative is more than just an advantage; it’s necessary. The businesses that are most likely to succeed are those that can anticipate and respond to change swiftly.

Digital transformation enables businesses to harness the power of data analytics, improve customer experiences, and automate processes for efficiency. It represents a profound cultural shift that requires organizations to challenge the status quo continually.

Pain + Reflection = Progress – Ray Dalio

Why Most Digital Transformations Fail

Despite its numerous benefits, digital transformations often fail to achieve their goals. Here’s why:

Lack of Clear Vision and Strategy

Digital transformation is a goal that takes time to be achieved. It’s a complex process that requires a clear vision, strategy, and patience. Many initiatives fail because they need clear objectives and a roadmap to get there.

Resistance to Change

People are typically resistant to change, especially when it’s as profound as a digital transformation. Many employees worry about job security or need help to adapt to new ways of working, leading to a lack of engagement and pushback.

Inadequate Leadership

Leadership plays a critical role in the success of a digital transformation. Inadequate or uninvolved supervision can lead to poor decision-making, a lack of direction, and failure. Because digital transformation is a fundamental rethinking of how a business operates, often it is leadership’s unwillingness or inability to change or lead the change which is a key contributor to the high failure rates. But leadership skills, like any other skills, can be developed.

The most dangerous leadership myth is that leaders are born – that there is a genetic factor to leadership. This myth asserts that people simply either have certain charismatic qualities or not. That’s nonsense; in fact, the opposite is true. Leaders are made rather than born. – Warren Bennis

Insufficient Skills and Expertise

Organizations often need more skills and expertise to navigate a digital transformation. This skills gap can result in inefficiencies, mistakes, and, ultimately, failure. Technology skills, design skills, communication skills, marketing skills and many others often need to be developed for digital transformation to deliver impact.

Leading a Successful Digital Transformation

While it may seem that digital transformations are fraught with risks and uncertainty, the sentiment that failure is inevitable couldn’t be further from the truth. Indeed, the right strategies can not only mitigate these risks but can pave the way for transformational success. By strategically aligning the technological capabilities with the core business objectives, securing organizational buy-in, fostering a culture of innovation, and investing in talent development, leaders can adeptly steer the digital transformation journey. Let’s delve into some of these crucial strategies that can chart the course for a successful digital metamorphosis.

Develop a Clear Vision and Strategy

You’ve got to start with the customer experience and work backward to the technology. You can’t start with the technology then try to figure out where to sell it. – Steve Jobs

Establish the clear customer or operational pain points to be improved; then define the outcomes – what’s the future vision of the customer experience or operational approach. With these two anchoring points, the current state and a future state defined, then establish an agile “test and learn” approach to testing.

Foster a Culture of Change

In the heart of every growing and vibrant company pulsates a culture of innovation, serving as the lifeblood for its growth and long term success. A blend of leadership, processes, resources, strategy and culture creates an environment where new ideas are not only encouraged but celebrated. When employees feel safe to take calculated risks and experiment, they break free from the shackles of convention, sparking insights and the struggle that drives innovative solutions. 

This spirit of innovation transcends mere product development and seeps into every corner of the organization – from processes to customer interactions, from strategy to execution. Thus, fostering a culture of innovation isn’t just beneficial; it’s crucial. It’s the engine that propels a company forward in an ever-evolving marketplace, ensuring not just survival, but a commanding lead in the race of relevance and success. As I always say, “culture is the most important ingredient to becoming a truly innovative company.”

A successful digital transformation requires a culture that embraces change, values innovation, and is willing to take calculated risks. Encourage open communication, provide ample training, and ensure employees feel valued and involved. This is the core of an agile culture – taking well calculated risks, testing them, and moving forward.

Lead with Commitment and Agility

If you’re co-founder or CEO, you have to do all kinds of tasks you might not want to do… If you don’t do your chores, the company won’t succeed… No task is too menial. – Elon Musk

True leadership, particularly in the context of digital transformation, demands more than mere passive involvement. It requires full commitment and active steering of the organizational ship, even in the face of choppy waters and unpredictable currents. Leaders must be willing to make difficult decisions, be it in terms of reallocating resources, redefining business processes, or even restructuring teams. This involves not just having a vision, but also a resolve to stick to that vision and see it through to fruition. Furthermore, they must possess the agility to swiftly adapt to changing circumstances, because in the digital age, change is the only constant. It’s about being present at the helm, guiding the organization towards the horizon of digital advancement, understanding the complexities of the journey, and having the courage to make necessary course corrections. This active, dynamic, and responsive style of leadership can truly make a difference in the success of a digital transformation.

Build the Necessary Skills and Expertise

“The ability to learn faster than your competitors may be the only sustainable competitive advantage.” – Arie de Geus

One of the most critical steps an organization can take is to invest in training and development programs that target existing skills gaps. This is a proactive strategy to empower your team and build internal capabilities. 

While the short-term temptation may be to primarily rely on external experts to fast-track digital projects, the long-term success of any digital transformation hinges on fostering a competent, self-sufficient team with a blend of employees and targeted expert contractors. Such a team, imbued with the right skills and backed by a continuous learning culture, can not only handle current projects but can also adapt and innovate as new digital trends and technologies emerge. 

Measure and Monitor Progress

Unless we determine what shall be measured and what the yardstick of measurement in an area will be, the area itself will not be seen.” – Peter Drucker

Craft a powerful set of key performance indicators (KPIs) as your compass guiding the course of your digital transformation. By diligently tracking these metrics, you can seamlessly calibrate your strategies, applaud wins, and maintain the transformative momentum. 

Constructing an equilibrium between different types of metrics is a nuanced art – starting with input metrics that shed light on customer pain points and operational bottlenecks, pointing towards opportunities for enhancements. 

Then, program metrics like budget allocation, resources used, and development progress offer a clear view of the unfolding transformational efforts. Lastly, output metrics like user adoption, the influence exerted, and improvements made underscore the true value of your digital endeavors.


Digital transformation is a challenging journey. It involves fundamental changes in how a business operates and engages with its customers. While many digital transformations fail, understanding these pitfalls and embracing the recommended strategies can significantly increase your chances of success.

Change is hard because people overestimate the value of what they have and underestimate the value of what they may gain by giving that up.” – James Belasco and Ralph Stayer

Remember, the goal of digital transformation is not merely about adopting new technology; it’s about leveraging technology to improve business processes, increase operational efficiency, and enhance customer experience. Remember this as you lead your business through the digital transformation journey.

John Rossman is the author of The Amazon Way: Amazon’s 14 Leadership Principles and is a leading leadership speaker on goal setting and high-performance teams. If you’d like to discuss your goals, let’s connect

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John Rossman | Leadership Keynote Speaker & Author