Digital Transformation Mistakes Guaranteed to make you Fail

Digital Transformation Mistakes Guaranteed to Make You Fail
Mistakes That You Should Avoid

Digital Transformation is a business practice today. And, as more and more organizations experiment with the concept, Digital Transformation mistakes are getting pretty common. With this blog, we hope to help you and your company avoid some of these mistakes and in fact improve your digital transformation journey.

Digital Transformation is a necessity, much like any other component of an organization, say HR, operations, and more. In many organizations, there are dedicated teams to formulate digital transformation strategies, optimize the process and to make sure the entire company transitions smoothly. Not having a dedicated team or even an offshore partner to track the digital transformation process could be the first mistake for most companies. 

We’ve read examples of Nike, Ikea, Domino’s Journey to digital transformation. However, looking at someone else’s success and trying to emulate that onto your own company is a completely different challenge. Mistakes are inevitable and one way to get around is to learn about them.

At Leapfrog, being an IT service company, we have always been at the forefront of technology and implemented the best digital practices to innovate and serve all our partners. We have closely worked with numerous organizations to help them with their digital transformation journey. So, the mistakes that we point out in this article are not just words on your screen. You could say, this is our first-hand experience and observation of the past 10 years.

Failure to acknowledge and Analyze the Impact of Digital Transformation

In our own experience, we have seen a lot of companies struggle to understand the impact of digital transformation. Assessing industry and impact led by digital transformation allows companies to accurately measure their value proposition, which in turn allows them to implement transformation strategies with the big picture in sight.

A lot of companies decide to invest in social media, or build their own app, or search for new technologies without fully understanding how it’s going to help their business. 

This is the key difference between companies in the same industry who are excelling in branding, customer experience and revenue generation and those who aren’t. In our experience, the companies that are successfully navigating the digital world, are clear about who they are, why they need to transform and the impact digital transformation is going to have in the future of their business.

What’s the solution?

Approach digital transformation as a journey of re-invention. One question to ask yourself would be: Why does your company exist? 

This is going to lead to some follow up questions, like: 

What does your company need to do in order to serve your purpose in the modern business world of digital technology?

When you’ve answered these questions, you move on to other digital transformation mistakes you need to avoid.

Holding on to Past Legacies

A lot of companies are living in the stories of their glory days. We’ve seen memes and tiktoks of how Blockbuster shut down along with many other companies who just couldn’t evolve with their market. The fundamental mistake that’s common for the mega companies of the past that are struggling to survive today is that they refused change. They failed to adapt to the rapidly changing world of digital technology and were left behind.

Even today, a lot of companies seem to be satisfied with the results of the past. Why fix something that’s not broken? This mentality is toxic in the business world. Business, or running an organization is not about fixing broken things. Rather, it’s about pushing innovation, finding new ways to contribute to the world; something we constantly strive for at Leapfrog.

“Change is the law of life and those who look only to the past or present are certain to miss the future.” —John F. Kennedy

What’s the solution?

Companies have to let go of the “Wait and see” mentality. There are certain stages for every evolution, and blindly investing money isn’t necessarily the solution either.

After you’ve avoided the first mistake (see above), the second step might be something like, What can we do to make our operations smoother? 

Will building an app help? 

You take it one step after another, keeping in mind that every transformation step is a necessity in order to build for the future.

Mismanage the Process of Digital Transformation

Messing up the management is probably the easiest thing to do regardless of the project or process you’re involved in. When the issue is about something like digital transformation, it only takes one mis-step to disassociate the management of the business transformation from the rest of the company.

It might be beneficial to learn about What is Digital Transformation before you make any business plans.

Successful digital transformation journeys always start from a committed board of directors or high level employees who are involved in the intricacies of every planning and implementation.

You have to be aware about the process. Earlier we talked about figuring out the bigger picture, and now you have to make plans to achieve it. Proper planning and implementation is not as complicated as the internet will have you believe. As long as you get the basics right, you will achieve your goals in the long run.

Proper planning allows you to correctly estimate the resources and infrastructure. Once you know your process, prepare a plan, estimate the resources, the next step is to get everyone involved. Only then, you can execute your plans effectively. Your transformation can only be successful if you and your employees, customers and stakeholders are on the same page.

What’s the solution?

Do your research. Try and understand the process and various elements of digital transformation to the best of your abilities. Then, communicate your plans and understanding of the process with everyone involved. 

“70% of digital transformations fail, most often due to resistance from employees.”

Read more Stats of Digital Transformation.

Here are some tips on how to maintain employee engagement during your digital transformation journey.

Once everyone is on the same page and understands the process, the execution is actually the easy part. Granted, following digital transformation strategies isn’t always enough. You also have to be mindful of the trends in the market.
You might find some useful information here. Key trends of digital transformation.

Predetermined Assumptions

Being able to form a collective picture of progress is a valuable skill when it comes to digital transformation. A lot of companies get trapped in the loop of inward thinking. Companies opt to go for a low hanging fruit that can only yield limited short term gain.

For example, companies might try to copy their competitors instead of analyzing the customers’ needs. This is often a result of a fixed mindset.

The CDO or the board of directors should be open minded to allow room for more opportunities. Nobody could have predicted that Movie halls would be on the verge of going bankrupt, but it’s happening. Nothing is permanent and we have to adapt our business models accordingly.

What’s the solution?

Stop believing in the myths. You have to remember that digital transformation means setting up your business for years to come, not just gaining maximum Instagram followers in three months.


Technology is in the heart of digital transformation. However, a lot of companies tend to lose sight of what transformation should deliver. Only focusing on technology means the companies might spend too much time and resources on “the next big thing”, which could be AI, IoT, or a vast array of technologies available to experiment on.

These are definitely important aspects of transformation, but the question you should ask yourself is, will your business benefit from this? Will you be able to see Return on Investment within a certain timeline?

Customers who have a bad experience with a website are 88% less likely to return. So, maybe as a business, you would be better off prioritizing optimization of your website to best suit your customers’ needs.

What’s the solution?

Executives and digital transformation leaders need to prioritize the most pressing problems to solve. It might be enhancing your customers’ experience through your website, making your operations smoother, or something as simple as making data entry more efficient.

Forget to take Cultural Barrier into Account

An organization is more than just operations and revenue. Anybody who’s worked in a team understands the value of organizational culture and values. When we talk about digital transformation, we often fail to address this important topic. Earlier, we talked about involving employees in the digital transformation process, however, it’s not just about completing tasks.

For instance, as the daily operations of an organization evolves, it’s crucial to redefine and create new roles in order to adapt to change.

What’s the solution?

Leadership must address the employee concerns. Addressing people’s fears and misunderstandings is a great place to start. The purpose of maintaining culture is to make sure people actually want to work for the company.

This might require reinstating the company values and core ideas. When employees feel comfortable with the company’s initiatives, they are more likely to feel comfortable switching roles and even departments for the greater good of the company.

Lack of Communication

Communication between multiple departments is key for digital transformation. However, it’s easier said than done. You might have noticed within your company as well. There is a lack of communication between departments despite our best efforts. It’s even tougher when the company is going through an overhaul.

Discarding old processes to create new ones takes time and people need time to adjust.

Another thing that often goes missing is failure to define new roles and responsibilities. Assuming that everyone will take a shape to fit the puzzle perfectly is the biggest mistake.

Another problem that might arise due to lack of communication is certain departments being forgotten in the transformation process.

What’s the solution?

Someone needs to take the lead of the digital transformation process. Chief Digital Officer is a new position we are slowly starting to see in companies that are serious about reinventing their business for the digital future.

The team lead can create a process to make sure the entire company goes through a simultaneous transformation.

Adopting selective approaches, instead of focusing on the bigger picture.

Stepping into the digital transformation journey while being selective of the people or process to be responsible for the transformation is another common mistake made by companies. Some leaders only focus on a limited part of the company to simplify and quicken the process instead of focusing on digital transformation as the core of the business. This kind of approach is way off the track.

At times, top-level management is so invested in digital transformation that they are the only one who is grinding to implement digital transformation. They completely disregard employees and employees also think that it is none of their business.

“It is the job of the IT department”. The most common statement we hear when people talk about digital transformation. It’s impossible to achieve digital transformation with such mentality.

What’s the solution?

Integrating digital transformation in every process of business operations is surely a challenge but it is totally worth it. Business leaders should be responsible to lead the way but they should make sure that the employees are aware of what is going on in the business. Maintaining transparency and building a healthy two-way communication bridge will definitely boost employee’s morale to take on the challenge together.

Digital Transformation Myopia

We have seen many companies setting short term goals and rushing to achieve them. Digital transformation is an ongoing, continuous process that is implemented to adapt to the dynamic business environment. But many companies are over-enthusiastic to meet the deadlines just to never look back at it again. We have seen many physical retail stores quickly providing online services through websites or social media and they define it as “digital transformation.” It is a step in the right direction but the journey doesn’t end there. 

Having short term strategies definitely paves the way to achieve the vision. But getting off midway without reaching the destination is one of the most common mistakes we have witnessed.

What is the solution?

The digital transformation journey could be overwhelming and achieving short term goals could certainly be motivating for the company. Rather than being satisfied with short term victories, they should treat it as a checklist on a long to-do list. And this reverts the discussion back to having a big picture.

Author’s note:

Digital transformation is a fun, tedious, and highly fruitful journey for every organization. It’s a process as opposed to a destination and that is the truth of the modern business. But, it’s worth it and that has been proven by countless examples of digital transformation.

As a Digital Service Agency, our own experience tells us that the companies that are aware of why they exist are able to maintain their success and ease through any transformation.

Book a Free 30 minutes Consultation about how Leapfrog can help you bring digital transformation to your business.

Praveen Shrestha

Praveen has been working in content creation and marketing for over 6 years. He believes his background in psychology helps him understand people better.

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