Addressing 5 Common Design Challenges in Enterprise Transformation

Tetiana Prokofieva
Yevheniia Sydorova
Daria Iaskova

A few years ago, research on enterprise digital transformation published by Deloitte revealed the striking statistics—70% of transformation efforts fail. Employee pushback, gaps in digital skills, executive reliance on legacy systems, or a lack of a holistic digital strategy—all of these factors are likely to make the undesired corrections to the company’s transformation agenda. 

Enterprise transformation makes a huge part of our expertise here, at Trinetix. As practitioners, we can confirm that no transformation comes without a challenge. But solutions to these challenges often lie in the plane of user experience, as the impact of each transformation is measured by the value it brings to end users.

In this blog post, we’ll look at five common challenges of digital business transformation and discover the ways to approach them using experience design best practices.

What is special about enterprise transformation?

Digital transformation takes time. This is especially true for enterprises, where each decision needs to go through a long corridor of validations and approvals from C-levels, line managers, and stakeholders.

The scale of enterprise companies often runs counter to the speed of today’s dynamic business landscape and makes digital transformation initiatives unsuccessful. Trying to keep up with the pace of the market, business executives are tempted by the desire to immediately bring innovation and adopt the changes within a reasonable time. 

At the same time, overlooking fundamental user experience research and neglecting feedback-gathering culture may result in digital transformation bringing no expected results. So, the principal challenge of enterprise digital transformation is aligning organizations’ complex structures with the desire to accelerate innovation adoption. Let’s uncover what it means in detail.

Key challenges of digital transformation

Years of digital partnerships allowed us to explore the barriers enterprises face on their way to digital transformation and define the key challenges that prevent them from getting desired results.

  1. Siloed organizational structures
  2. Internal reliance on legacy systems and workflows
  3. Lack of innovation-first company culture
  4. An inconsistent approach to growth and innovation
  5. Financial constraints slowing down the transformation process

Let’s break them down into meaningful details and find solutions that lay in the plain of transformation design. 


Siloed organizational structures

With enterprises having complex organizational structures, digital transformation is often characterized by biases and inconsistency of top managers’ and stakeholders’ opinions

Our experience shows that enterprise executives tend to focus on speeding up the transformation processes to gain a competitive edge. As a result, they skip gathering requirements from different business units and neglect to do UX and market research, considering them a waste of time in the long run. 

In this case, the entire digital transformation process is built on narrow business objectives or needs of a particular business unit and, as a result, brings no measurable outcomes. Having an incomplete picture of a company's operations becomes a serious roadblock to digital transformation’s success.

How can design help? 

In reality, collaboration is the main fuel of enterprise digital transformation, as it helps to break down silos and achieve consensus on the next steps. Leveraging a consistent approach to solution design and harnessing an open feedback-gathering culture can help enterprises subordinate digital transformation to their specific business challenges and focus on impact rather than chase innovation per se.

Experience design best practices allow enterprises to pay attention to a company's genuine needs and foresee the results of the changes. Design workshops, collective brainstorms, observations, and feedback sessions uncover deeper insights into users' behavior, thus helping C-suites look at the transformation from a different angle.

Form a unified product vision and align expectations with ease

Internal reliance on legacy systems and workflows

Sometimes, enterprise digital transformation is blocked on the technology side, and that’s completely justified. Developing a universal solution that would be used by a huge group of people on a regular basis is not just a time-consuming but not-so-easily feasible endeavor. And of course, there are a number of constraints to take into account. 

Why should we invest millions of dollars into destroying something that luckily keeps on working?”– this is the not lacking humor question we occasionally hear from enterprises that remain reluctant to change.

This is another concern dictated by the failures organizations might have experienced approaching enterprise-scale changes in the past. According to the ABBYY Digital Transformation Survey, 36% of senior executives consider replacing legacy systems to be the main challenge in digital business transformation.

How can design help?

Often, being bound to legacy software systems is dictated by the fear that a transformation will make employees learn to use new cumbersome systems, resulting in operational slowdowns and digital friction.

Design helps to reduce the complexity of innovations and boost the enterprise's adoption of new tools and technologies. Implementing intuitive user flows and enabling a seamless connection between multiple components of an enterprise system allows to create a holistic solution and helps organizations transform natively and smoothly. 

Lack of innovation-first company culture 

Employee pushback is often called a major barrier to digital transformation. A report by KPMG revealed that 19% of employees lack the technical skills required to implement or fully take advantage of new enterprise systems.

But what is important to recognize is that resistance to changes often comes from the top. According to the above-mentioned survey, 23% of global respondents experience difficulties getting buy-in from their senior management. 

At the same time, by harnessing a proactive digital-first culture and seeding innovation into an organization's DNA, enterprises are bound to achieve better transformation results. By developing employee digital dexterity and understanding the real value of the transformation, companies can embed innovation and digital literacy into their corporate culture, thus unlocking new growth opportunities and creating a long-term competitive advantage. 

How can design help? 

Organizations often remain hesitant about innovation when their understanding of its value is incomplete. Design helps humanize enterprise transformation by prioritizing the end users of digital solutions.

Comprehensive user experience underlies modern digital workplaces and allows enterprises to remain productive throughout the transformation processes. Once recognizing the difference brought by value-centered innovation, enterprises embrace changes as an irreplaceable part of a company's growth strategy to preserve agility and open-mindedness and stay ahead of the competition.

How to make sure your digital workplace is up-to-date?

An inconsistent approach to growth and innovation 

Getting started with digital transformation, organizations are often challenged by the need to create a sustainable system, capable of embracing future changes in a native and consistent way. In other words, they need not just to give the transformation a go but make it scalable at an enterprise level.

Let’s say a company uses a corporate space for online collaboration. When it comes to increasing process complexity, launching a new product line, or onboarding more employees, it’s always about the time needed to put things on track and make the system functional. At the same time, spending too much time may cost enterprises part of their revenues and result in reputational losses. 

How can design help? 

Investing in a scalable design system can help enterprises natively adopt innovation and become future-ready. Using a set of reusable components helps companies grow the functionality of complex systems and adjust workflows to help teams remain productive throughout the transformation process.

A scalable design system allows to speed up the growth and adoption of new features that make part of digital solutions by providing end users with a consistent and intuitive experience. 

Such a human-centered approach to business scaling pays off and prepares organizations for whatever changes, integrations, and curves the future holds.

Financial constraints questioning the transformation

Digital transformation is also a question of money. The stakes here become even higher when it comes to the transformation happening at scale. An average enterprise digital transformation requires a company to spend at least $27.5 million of its annual budget. This fact significantly slows down innovation adoption and complicates the transformation process.

As a rule, when there is a choice between providing value to the external consumer and introducing the changes that target employees, companies tend to choose the former—believing that developing new products and features will bring them higher ROI and help better address the needs of their target audience. In reality, they may simply approach digital transformation in the wrong way. 

How can design help? 

Digital transformation design affects the financial aspects of enterprise digital initiatives in a few different ways.

  • Human-centered, value-driven experiences streamline enterprise processes and workflows, thus boosting operational efficiency and increasing revenues.
  • Making end users the center of digital transformation allows businesses to get better results and improves employee satisfaction. As a result, workers feel more engaged and remain productive doing their jobs. 
  • Once investing in developing a holistic digital transformation strategy, organizations contribute to creating a sustainable business future, can avoid situational budget spending, and become 360-degree ready for scaling. 

How design enables the success of enterprise digital transformation 

Design prevents costly mistakes and helps ensure that future transformational changes are aligned with what employees feel on the ground floor. Incorporating user feedback into the digital transformation process improves adoption of changes.

Design is a universal tool that provides end-to-end support of digital initiatives at an enterprise scale. In fact, it gives substance to any change that happens within an organization and underlies a company's understanding of digital transformation.


From helping to uncover deeper process dependencies to creating meaningful user experiences that revolutionize enterprise operations, design brings success to each level of transformation. 

Unlock your growth potential by removing legacy roadblocks

Just like any future-forward business change, enterprise transformation has its own challenges to address. But operationalizing at scale, you always need to think proactively and have a broader view of your organization’s landscape. 

For years of digital partnerships, we developed a number of successful digital enterprise transformation solutions. None of them, however, would be possible without a user-centered design approach. If you are up for a strategic change, let’s chat about sharing the responsibility with a team of transformation practitioners and see what we can achieve together!  


While digital transformation is often associated with implementing new technologies and performing major infrastructure changes, in reality, it’s design that helps organizations adopt the changes and close the loop. Intuitive user flows, comprehensive UX copy, and a consistent system of design components help companies onboard new features and embrace the change.
Transformation design is an iterative and consistent design approach used to apply changes to complex large-scale systems. It deals with bringing fundamental changes to individuals' mindsets, organizational structures, and tech assets that support their work.
Trinetix's approach to digital transformation combines a discovery-first process aimed at identifying opportunities for sustainable business growth with strong tech expertise acquired during years of experience with multiple enterprise areas and domains. We harness a proactive impact-oriented culture and bring utmost dedication that helps enterprises achieve measurable results and grow.
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