Why does your Digital Strategy Fail?

May 1, 2023
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According to CIO Magazine, digital-first companies are 64% more likely to achieve their business goals than their peers. In fact, 56% of CEOs surveyed say digital improvements have led to increased revenue. These digital improvements are almost always a part of a larger digital strategy and digital transformation process.

So, What is Digital Strategy?

A digital strategy can revolutionize the way your organization thinks about your business goals and priorities, and help move you towards a digital-first era in the way products, services and experiences are delivered.

A comprehensive digital strategy takes into account business vision and goals, customer and employee expectations, market competitiveness, and business technologies, to form a footprint of the digital transformation.  It forms a roadmap to digitize an organization that will meet both short- and long-term business demands.

However, most businesses lack the skills to develop an effective digital strategy. Below are the most common issues with developing and implementing digital strategies:

1.     Lack of Alignment with Business Priorities

The organization’s digital strategy is not aligned with its business context and priorities. This can often be because leadership has difficulty identifying the business context. This lack of clarity impacts the creation of the digital strategy which then results in a strategy that is not clear enough for employees to understand.


Instead of guessing what your business needs, a deep dive will help you align your business goals and your digital goals. This will not only support your digital transformation but will also align your whole team and give them a purpose. This clarity around goals and the communication of these goals is critical since 70% of digital transformations fail, most often due to resistance from employees (Source: CIO Magazine).

2.    Leadership and Management Void

Digital strategy can fall apart if there is no strong centre holding the digital initiatives together. Your organization may have a roadmap of initiatives for the next three or five years but without management and leadership, you might be setting yourself up for executional failure. There is also a risk that your strategy becomes immaterial with no one responsible for adapting it, especially if market dynamics shift or disruptive innovation occurs.


Establish a Digital Transformation Office or hire a Chief Digital Officer. This will be your strong centre. Companies with an engaged Chief Digital Officer are 1.6 times more likely to report a successful digital transformation (Source: CIO Magazine).

A Digital Transformation Office (DTO) or a Chief Digital Officer (CDO) will support two critical aspects of your organization’s digital transformation: 

  1. Visionary Leader: The DTO and CDO are the change agent and visionary. They are creative, insightful and innovative about digitalization.
  2. Implementation Expert: The DTO and CDO will support the successful implementation of your digital strategy. They will ensure process standardization and delivery management. They will help your organization keep up the momentum, rigorously tracking progress and providing a signal when it’s time to adjust course. 
3.    Inflexibility and Not Thinking Big Enough

Digital strategies can fail because of too little ambition. Don’t be inflexible. Don’t be overly committed to your current tech stack or the legacy business model.

Did you know that Kodak created the first digital camera in 1975? But they were too married to their film and photo printing business to see the opportunity in digital photography. Kodak might still be around if they hadn’t made this mistake.


Start by thinking big. 80% of companies say their digital transformation efforts involve multiple business units or the entire company (Source: CIO Magazine). You can always scope down your digital strategy if you need to. But the best digital strategies need to be big picture to move the needle on value creation.

Let Us Help You Ensure A Successful Digital Transformation!

Our team of experts can help lead your organization on your digital transformation journey. We can help you assess your current state, plan your digital strategy, and implement it. Your first step is to contact us and we can bring your vision to life!

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Farzad Khan

Founder & Principal
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