Driving Successful Digital Transformations: Observations from a Chief Digital Officer

By Rob Milstead, SVP and CIO, The ReThink Group


Over the last fifteen years, digital transformations have become paramount for large corporations as they react to changing customer expectations driven largely by mobile technology and high-speed data access. Companies like Amazon, with their ease of use and convenience, changed consumer expectations permanently and companies of all types have had to react to drive revenue growth and profit improvement while improving the customer experience.

Recently, there have been a variety of studies that find the majority of digital transformations aren’t seeing the anticipated results and in the worst cases, are complete failures.

With experience as a consultant advising from outside a company and as a Chief Digital Officer and Chief Information Officer from inside organizations undergoing transformations, I have a variety of hard-earned insights into what it takes to navigate this complex terrain.

A successful digital transformation is a multifaceted endeavor that requires strategic vision, committed leadership, and a culture of adaptability. By following these principles and heeding the key lessons learned, organizations can navigate this transformative journey with confidence and achieve enduring success in the digital age.

Key Elements in Starting a Digital Transformation
  1. Clear Vision and Strategy:

The cornerstone of any successful digital transformation is a clear, well-articulated vision and strategy. This should align with the company’s overall business objectives and outline how digital technologies will drive growth, enhance customer experiences, and optimize operations. Since transformation can take a long time, this must be simple and easily understandable by employees to help reorient and unify the team when normal distractions and competing business initiatives may impact the focus required to drive success.

  1. Leadership Commitment:

Commitment from top leadership is non-negotiable. It’s imperative that executives not only endorse the transformation but actively champion it. This shouldn’t be just from the digital leader, but the key marketing, sales and operational leaders that own the teams that often will be doing things differently after key process and technology changes are a part of digital transformation. This sets the tone for the entire organization and ensures that resources, both financial and human, are allocated appropriately.

  1. Agile Culture and Mindset:

Instill an agile culture that embraces change, experimentation, and continuous learning. This involves empowering employees at all levels to contribute ideas and providing them with the tools and training needed to adapt to new technologies. This can be quite challenging for large companies and especially public companies.  Often, the technology teams go first by changing their development approach, but I’ve seen the most success when business teams participate heavily in introducing agile principles in identifying customer needs, developing requirements, and helping define priorities across the company.

  1. Customer-Centric Approach:

Placing the customer at the center of your transformation efforts is pivotal. Understand their needs, preferences, and pain points, and design digital solutions that address these effectively. Regular feedback loops and customer journey mapping are essential tools in this regard. This is harder than a lot of companies believe, but doing this correctly often involves new skills to understand qualitative and quantitative techniques to understand customer behavior and translate it into insights to inform technology and process change roadmaps. 

Execution and Implementation Observations
  1. Prioritize and Sequence Initiatives:

Not all initiatives are created equal. It’s crucial to prioritize projects based on their potential impact and complexity. Start with quick wins to build momentum, but also have a long-term roadmap that outlines the broader transformation journey.

  1. Cross-Functional Collaboration:

Break down silos and foster collaboration across departments. Digital transformations often require multidisciplinary teams to work together seamlessly. Encourage open communication channels and establish forums for knowledge sharing.

  1. Innovation Ecosystem:

Cultivate an ecosystem that supports innovation. This includes partnerships with startups, accelerator participation, and even in-house innovation labs. Such collaborations can provide access to cutting-edge technologies and fresh perspectives. This can be hard in a large company, so carving out any amount of budget to help fund various pilots and learning opportunities is critical in finding new ways to add value and support the culture change that needs to be in place long term.

  1. Change Management and Training:

Acknowledge that change can be met with resistance. Implement robust change management strategies that include clear communication, stakeholder engagement, and training programs. Ensure that employees have the necessary skills to leverage new technologies effectively. This will require continued focus and is not a one-time activity. The company and its employees will get distracted as new initiatives compete for focus and budget over the long term.

  1. Iterative Approach:

Embrace an iterative approach to development and deployment. Continuous feedback loops from customers and internal stakeholders are vital for refining solutions and adapting to evolving business needs.

  1. Data-Driven Decision Making:

Leverage data as a strategic asset. Establish robust data management and analytics capabilities to derive meaningful insights. This not only informs business decisions but also enables personalization, automation, and predictive capabilities. This is also a mindset shift in not only gathering data, but learning how to behave differently as an organization. So often, organizations have data, but still rely on instinct and the opinions of the most senior leaders.  Now, with machine learning and artificial intelligence on the rise, companies have to learn to trust models that are predicting and prescribing actions that may be counterintuitive.

My Key Lessons Learned
  1. People are the Core of Transformation:

Success hinges on the people driving the transformation. Invest in their development, create a supportive environment, and ensure they understand and embrace the vision.

  1. Fail Fast, Learn Faster:

Embrace a culture that celebrates experimentation and learning from failures. This accelerates the pace of innovation and ensures that mistakes serve as valuable learning opportunities. Acknowledge that the digital landscape is in a constant state of flux. Be prepared to pivot and adjust strategies as needed. Flexibility allows for seizing new opportunities and mitigating risks effectively.

  1. Balance Innovation with Stability:

While innovation is crucial, it must be balanced with the need for stability and operational excellence. Strive for a harmonious coexistence of cutting-edge solutions with robust, reliable systems.

  1. Communicate Relentlessly:

Effective communication is the bedrock of successful transformation. Ensure that the vision, progress, and wins are consistently communicated across the organization. This needs to occur up, down, and across the organization more often than you may imagine. Teams attention spans are short and they will need reinforcement regularly to maintain awareness, interest, and collaboration.

  1. Manage Competing Priorities:

Since a digital transformation may span many years of work, two things are likely to happen. First, fatigue in the organization will happen.  Often, teams are doing their day jobs and trying to support new capabilities being built. Consultants may also be a part of the transformation and it’s just a reality that fatigue will occur towards the consultants and their seemingly endless meetings and action items.  Leaders must be aware and consistently address fatigue to let teams know they are valued and work to maintain momentum. Second, there will inevitably be new initiatives that are suddenly competing for attention and effort.  Acquisitions, competitive shifts, market dynamics, and other factors are simply the reality today. You and your teams have to be ready to address and pivot.

In conclusion, a successful digital transformation is a multifaceted endeavor that requires strategic vision, committed leadership, and a culture of adaptability. By following these principles and heeding the key lessons learned, organizations can navigate this transformative journey with confidence and achieve enduring success in the digital age.

Rob Milstead is a seasoned digital leader having led large initiatives in numerous companies over the last 30 years. He has experience in consulting and corporate leadership connecting business strategy, enterprise technology, and exceptional customer experiences.