A Digital Transformation Roadmap for Every CIO

A Digital Transformation Roadmap for Every CIO

With the advent of the digital era, every company is involved with digital technology in one way or another. IT leaders are taking the center stage as organizations face a new digital reality. 

Organizations have understood the severity of this new reality and are undergoing Digital Transformation. With that comes new digital technologies and business models which can bring about a significant change for the business. 

The efficacy of the implementation of such initiatives decides whether its impact is positive or negative. The ideal way would be to create a Digital enablement strategy and combine it with Digital Transformation Roadmap.  Doing so helps navigate organizations through their Digital Transformation efforts. 

What is a Digital Transformation Roadmap? 

A Digital Transformation Roadmap is a set of steps that organizations can follow to achieve short-term and long-term business goals with the use of digital technology. 

The roadmap begins by understanding business needs and finding gaps in the existing system to build a strategy that avoids these gaps.  

Related Read: The practical guide for CIOs to initiate Digital Transformation 

How to Build a Digital Enterprise Transformation Roadmap? 

Digital Transformation is a long journey and even with a solid strategy in hand, organizations must be patient with the process and must put in effort for a long time to see it succeed. 

i. Assess the Current State  

The aim is to assess the current business state by identifying favorable internal and external factors. Based on this, take action in areas where there are gaps or flaws. 


Frameworks like SWOT, STEEP, or STEEPLE analysis can be used to measure these internal and external factors. 

SWOT: It evaluates any business, project, or transformation efforts based on their Strengths, Weaknesses, Opportunities, and Threats. It helps identify the digital capabilities of the organization. Even though it helps you analyze both internal and external factors, it is predominantly used to identify internal capabilities.  

STEEP: With STEEP analysis, you can measure political, social, economical, environmental, and technological factors. It goes beyond SWOT analysis and gives an in-depth understanding of the current state of your digital capabilities. STEEP is one of the best methods to analyze external factors. 

STEEPLE: It is just like STEEP but with added capabilities as it considers the legal and ethical factors which help you even identify cultural and compliance gaps within the organization. You can include these factors in your roadmap to improve the organization’s culture along with its digital capabilities. STEEPLE can be a bit tedious when compared to STEEP and SWOT methods.  

ii. Develop a Vision and strategy 

Now that you know all the possible gaps and flaws of the company. It is time to create a strategy that aligns with your business aspirations and goals. Once this part is sorted out, you can go ahead and set an implementation plan. 

While creating this plan, it is important to consider the latest Digital Transformation trends as they will act as a base for the future. 


Let’s say you are a retail business that has both offline and online stores. You want to understand customers better and enhance their experience across all platforms. To achieve this, you have to enhance your online capabilities to identify what they want whenever they interact with your brand.

You start investing in tools and resources which can map the user’s journey across all platforms and collect crucial data which can tell more about their preferences and behavior. 

Based on this data, you can suggest them better deals through both online and offline stores which will enhance their experience with your brand. This way you can achieve your goal of enhancing customer experience using digital means.  

iii. Start with Rewarding Projects  

Start the Digital Transformation journey with projects that are less complex, easy to deploy, valuable, and financially viable. The idea is to get a return on your investments at the earliest.  


Waiting for all existing projects to be completed to get a final verdict on the success of your transformation initiatives is just a waste of time. Each project must have its own goal that makes it self-sufficient. If things go out of hand, you can always restart that particular project instead of the entire Digital Transformation initiative. 

iv. Deliver in Phases  

Digital Transformation is a complicated process and deploying it in one go is usually impossible. Businesses must focus on executing the transformation efforts in a phase-wise manner and on testing the project in a focus group before scaling it up. 

Divide the Digital Transformation plan into measurable tasks to get a more granular view of your initiative. 


Let’s take the example from point 2, a company that wants to provide a better customer experience. Now they can either go ahead and execute it as a whole or they can segment it in executable phases. In this case, they have segmented it into 4 phases.  

Phase1: Optimization of existing processes and automating the mundane tasks for better employee output. 

Phase 2: Digitizing most of the new processes across all channels and platforms. 

Phase 3: Integrating all digitized channels and processes together for better visibility and improved decision-making. 

Phase 4: Ensuring the success of this digital ecosystem and new business models with successful learning and development programs

Phase 1 ensures that repetitive tasks are automated to save employees time. Relevant existing processes are optimized for better outcomes. In the subsequent phases, the company digitized processes, integrated the ecosystem, and ensured training for a better customer experience. 

These phases can further be divided into “N” number of segments but it varies from business to business. 

v. Build Capabilities on the Fly 

Modernizing core operating infrastructure and processes helps organizations to enhance their digital experience for both customers and employees. 

With new infrastructure, comes the responsibility to hire new talent and to train existing employees. IT and Business leaders must both be involved in creating a cohesive training program to benefit their transformation efforts. 


The training and expertise provided to existing employees will not provide any real value to your business once you revamp your processes. Even with years of experience, most employees find it hard to navigate through new software. This is why providing continuous training is crucial. 

Business leaders need to understand that there are two types of skills required for success; job-related and application-oriented. 

The approach for training for both these skills will change, as you may need to hire new employees for job-related skills or create an online training program for existing employees. However, this approach may not work for application-related skills.  

Training employees on any application should be an ongoing process and for that, tools like LMS and Digital Adoption Platforms can help.

What’s Next? 

IT projects will run behind schedule, processes will have gaps, training won’t be sufficient and new regulatory issues will emerge. With the right tools and strategies, these issues can be solved and there is no defined formula for success. Any company has to act on the outline created and improvise as projects proceeds.

Digital Adoption Platforms can provide support with identifying gaps in processes, improving the quality of training, creating readily available training content, and guiding employees with their day-to-day tasks. 

For succesful digital transformation select Apty

Krishnan Kaushik
Written by Krishnan Kaushik

Krishnan is a Marketer and Content Crafter. He has an in-depth understanding of Digital Adoption, Transformation, and Enterprise applications that helps business to generate business outcomes. In his former life, he was an IIoT & Automation engineer. You can find him trying new recipes, riding a bike, and wondering about the most complex object on the face of the earth i.e Human Brain.

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