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8 Steps to a Winning Digital Transformation Strategy

Explore how digital transformations are planned and executed. Define your business goals, aligning with your organizational values to develop a winning digital transformation strategy.

What Is a Digital Transformation Strategy? 

A digital transformation strategy is a plan for reshaping existing business models and changing organizational culture while adopting digital advancements. The digital transformation roadmap results from analyzing your current state of business, the need to make the transition, and the goals you wish to achieve. 

However, only 35% of organizations’ digital transformation efforts are successful.

An organization’s plan for digital transformation does not only include digital modernization and adopting new business patterns. It’s a process that aims to transform organizational thinking toward adaptability to changes, customer focus, and learning culture. 

A good digital transformation strategy aligns with the business goals and seeks specific outcomes such as improving work process efficiency, increasing growth or lowering operational costs.

Why Is It Important to Build a Digital Transformation Roadmap? 

Developing a systematic roadmap for your digital initiative ensures that the goals and focus of the transformation are clear. Whether you need to deal with workflow inefficiencies, in response to competitors or drive innovation, a well-documented digital transformation strategy keeps the goals in check.  

A good understanding of what you intend to achieve will help you align everyone around your common goals and contribute to better coordination of the digital transformation efforts.

How to Develop a Digital Transformation Strategy in 8 Steps?

Whether it’s a pilot team or the entire organization, a digital transformation strategy starts by identifying your business goals and objectives. The steps below can help you define your transformation plan. 

1. Identify business goals. Understand the business goals you seek to achieve through digital transformation. This could mean optimizing your work processes’ efficiency or employee performance, improving customer experience, and expanding into new markets. 

2. Assess current technological maturity and market conditions. Analyze your present technology infrastructure, applications, processes, and employee skillset and evaluate the ongoing market trends and technology disruptions. This will help you identify your technology strengths, weaknesses, and areas of improvement. 

3. Determine investments. Upon analysis of your current technological landscape, identify the investments that align with your organizational goals. This could include upgrading existing systems, investing in new technologies, and shifting from traditional project management to exploring different Agile methodologies, training, and coaching initiatives. 

4. Nurture a digital culture. Digital transformation does not just involve technologies, it’s a broad initiative that also seeks organizational culture change and creating new behaviors. Ensure that the laid-out transformation initiatives align with your company's values and traits that have been working for your organization so far. Aim to enhance the culture with new ways of thinking and working.

5. Start small but with a strategy in mind. Initiating a digital transformation on a small scale with a pilot team or project can help you scale digital and Agile transformation across the enterprise. Identify initiatives that align with your business goals, and track closely how they unfold. The learnings and insights will improve your scaling journey.

6. Set up a dedicated team. A dedicated team can focus solely on digital transformation initiatives, allowing them to develop deep expertise in the relevant technologies and processes. They foster better communication and collaboration among team members, leading to a more cohesive and efficient transformation effort.

7. Define success measures. Set specific success metrics to help you track the progress of your digital transformation strategy. This will enable you to take prompt actions if and when needed.

8. Embrace experimentation and continuous learning. Digital transformation is not a one-time destination. It is an ongoing journey. Successful companies continuously experiment with new technologies, gather data on the results, and adapt their strategies based on what works best. This requires a culture of innovation and a willingness to learn from failures.

While all of the above steps are important, a digital transformation should bring tangible benefits that help your organization achieve its goals. Furthermore, digital transformations are dynamic, just as technology innovations nowadays. Hence, a winning strategy is oftentimes evolving. Ensure you are flexible and ready to adjust your plans as necessary.

digital transformation strategyExample of a digital transformation strategy roadmap

Important Factors to Consider When Making a Digital Transformation Roadmap 

Besides alignment with the company goals, other key driving factors of digital strategies include better customer experience, business resilience, and improved employee performance. (Source: IDG Inc.

  • Customer experience: Understanding your customer’s needs and expectations is critical to developing a successful digital transformation strategy. Whether you would have to create new communication channels or be more active on social media, with customer experience at its highest level, enhancing in that area and delivering value should be the focus of your strategy. 
  • Risk management: Digital transformations often involve making significant changes to the technology stack, processes, work culture, and ethics. That’s why your strategy needs to include a risk management analysis that identifies such potential risks and mitigates their impact. 
  • Continuous improvement mindset: Digital transformations are ongoing initiatives that should not be time-boxed. As such, a transformation strategy needs to provide opportunities for continuous improvement and learning to ensure that your organization achieves the set goals and stays ahead of the curve.

Who Should Be Involved in Digital Transformation Planning? 

Another critical factor in creating a winning digital transformation strategy is having the right members on board with the initiative. Some key roles include executive leadership, designated change leaders, and implementation leaders. 

  • C-level leadership support is crucial to initiating the transformation, not only in terms of allocating the budget. Their commitment and enthusiasm for the change are critical to achieving an organizational shift in the culture and spreading the digital-first mindset across teams. Key drivers of the transformation may include internal business stakeholders, digital planners, or external experts in the field of digital initiatives. 
  • Change leaders are the digital transformation champions who drive the initiative. They come from various teams across the value creation process, from client-facing teams to design and operations, and serve as proponents of the vision behind digital transformation. Such roles may include a Chief Information Officer (CIO), Digital Adoption Management, or Digital Product Manager. 
  • Customer experience team members should be involved in defining customer needs. They need to ensure that the adopted technologies during the transformation process enhance the customer experience.


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In Summary

A digital transformation strategy is a strategic map of your efforts to adopt digital technologies to help you achieve your higher organizational goals. These may include improving customers’ experience, increasing growth, enabling business resilience, and maximizing team and process efficiency. 

There are 8 important steps to developing a successful digital transformation strategy: 

  1. Identifying business goals 
  2. Assessing the current technological maturity
  3. Defining investments 
  4. Nurturing a digital culture 
  5. Ensuring a strategy is in place 
  6. Setting success measures
  7. Refining your strategy
Nikolay Tsonev

Nikolay Tsonev

Product Marketing | PMI Agile | SAFe Agilist certified

Nick is passionate about product marketing and business development and is a subject matter expert at Businessmap. With expertise in OKRs, strategy execution, Agile, and Kanban, he continues to drive his interest in continuous improvement. Nick is a PMI Agile and SAFe Agilist certified practitioner.

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