Turning the Corner on Digital Failure — Strategy, Storytelling & Outcome-Driven Adoption

In my previous edition, we explored the top five reasons digital transformations fail—and offered practical ways to course-correct. Despite significant investment in time, money, and effort, research shows that 70% of digital initiatives still fall short. That’s a staggering statistic—and one that continues to surprise leaders across industries. While quick fixes can help regain momentum, lasting success requires a different approach. So in this one, we are flipping the question: instead of asking why digital transformations fail, let’s examine what sets the successful ones apart. Based on my experience and conversations with fellow transformation leaders, two themes stand out—a clearly communicated “why” and a disciplined focus on the right metrics. In other words: storytelling and KPIs.

Let’s explore how pairing a compelling narrative with the right metrics can directly address the five most common reasons digital transformations fail.

Issue #1 - No clear strategy or alignment

Solution - Clarify the business case for digital transformation by connecting technology investments directly to measurable business outcomes. 

A successful digital transformation starts with a clear, unifying narrative—one that connects your digital initiatives directly to the organization’s vision, values, and growth priorities. This story isn’t just for messaging; it’s a strategic tool that brings the CIO, CFO, COO, and business unit leaders together. The C-suite can start by jointly examining where processes intersect across departments, identifying inefficiencies, and clarifying where technology can unlock value. Then, involve business unit leaders to ground those conversations in day-to-day realities. Encourage business leaders to involve their teams in these conversations to harness the collective wisdom across all levels of the organization. This type of deep involvement will surface issues and obstacles that can be effectively planned for in advance instead of managing reactively plus everyone will get a sense of how their individual work will be elevated through this project. When stakeholders understand why the change matters—whether it's to drive growth, improve efficiency, or enhance customer experience—alignment becomes far easier. A strong, enterprise-wide narrative breaks down silos and ensures that technology decisions are rooted in business outcomes that everyone, from executives to frontline teams, can stand behind. 

Bold Take: You have subject matter experts on every team! Make sure to involve them early and consult them often!

KPIs:

• Alignment scorecard

  • measures continuous alignment with goals via executive surveys.

• Percentage Reduction in Manual Processes

  • tracks overall decrease in manual effort over time.

• Time Saved per Process

  • measures efficiency gained through automation or workflow redesign.

• Automation Coverage Ratio

  • shows how much of the workflow is now digitized or automated.

    
    

Issue #2 Underinvestment in Change Management

Solution - Make change relatable by showing how it improves real work. 

Change efforts often fall short when they’re perceived as top-down mandates or disconnected from the realities of daily work. If you’ve already brought together a cross-functional team of subject matter experts—as discussed above—you’re ahead of the curve. But alignment alone isn’t enough. One of the most common pitfalls in digital transformation is framing it purely as a technology initiative. This narrow view not only misses the mark—it can actually diminish the perceived value of the entire effort. Technology is the enabler, not the end goal. To drive real engagement, shift the conversation from systems to outcomes: how will this make work easier, improve collaboration, and support the organization’s long-term success? Clearly point out how tedious tasks will be diminished and how more interesting and higher level work can now get done. Frame change as an opportunity for growth, not a tech upgrade. When employees see how the change benefits them—and the broader mission—it becomes tangible. A well-crafted narrative connects the transformation project to what employees care about, building trust, personal relevance, and faster adoption.

Bold Take: Make change relatable, not transactional

KPIs:

• Workflow Touchpoints per Process

  • fewer touchpoints often reflect more streamlined, automated workflows.

• Digital Workflow Completion Rate

  • measures how often a process is completed fully through a digital system without manual intervention.

• Achievement of Transformation Milestones

  • tracks whether transformation goals are being met on time and within scope — with adoption as a leading indicator.

  
  
  
  

Issue #3 - Gaps in Talent and Digital Capability

Solution - Embrace upskilling and re-skilling as a continual business necessity

As a leaders, we believe investing in upskilling is not optional—it’s essential. The pace of technological change is relentless, with new tools and platforms emerging almost daily. Staying current isn’t just about keeping up—it’s about making informed decisions on what’s relevant and valuable to our work. That’s why prioritizing both time and budget for professional development across your team is essential. Whether through conferences, workshops, peer exchanges, or hands-on training, continuous learning must be part of the culture. When team members are encouraged—and funded—to explore areas like AI in finance or automation in reporting, learning becomes purposeful, not reactive. Over time, this commitment builds a growth mindset and positions both individuals and the organization to adapt, innovate, and lead.

Bold Take: Treat skills development as an imperative on your team. 

KPIs:

• Digital Skill Gap Index

  • quantifies how widespread the skills gap is within the transformation-critical workforce.

• Skills Development Progress Rate

  • measures the effectiveness of training and reskilling efforts.

• Self-Reported Digital Confidence Score

  • gauges mindset, not just ability—important for adoption and sustained usage.

Issue #4 - Poor Data Foundation 

Solution: Reframe data as a business asset, not an IT expense

Strong data governance is essential for growth, risk management, and informed decision-making—but it only gets traction when leaders see it as a strategic priority. From personal experience, we can confidently say that a unified, standardized data foundation is key to scaling decision making and accelerating innovation. Most organizations lack this foundation and getting there can be difficult and contentious without the right leadership. That’s where collaboration with your technology team becomes critical. Partnering with your CIO can bring clarity, structure, and best practices to the table. Together, you can craft a narrative that positions data not as a cost center, but as a strategic asset. Framing data governance this way shifts the conversation from compliance to competitive advantage. Without consistent definitions and standards, even the most sophisticated enterprise platforms will fall short. Data discipline isn’t just IT’s responsibility; it’s an organizational commitment. Involve stakeholders across departments in shaping these standards so they reflect the realities of the business.Cultivate the mindset of “trusted data as a business asset” elevates data governance from a technical project to a core driver of growth, risk management, and decision-making. When every team understands the value of creating a single source of truth, they’re more likely to engage—and that’s when the real transformation begins.

Bold Take: Shift data governance from a backend task to a competitive advantage the entire organization depends on.

KPIs:

• Data Quality Index

  • a composite score measuring accuracy, completeness, consistency, and timeliness of critical data sets.

• Percentage of Standardized Data Elements

  • proportion of critical data elements that conform to defined data standards, formats, and taxonomies.

• Data Dictionary Coverage

  • percentage of enterprise data elements defined and catalogued in a centralized data dictionary or metadata repository.

Issue #5 - No quick wins = No momentum

Solution: Focus on visible results early on to show real value of the project.

Even with all the right planning, a transformation effort can quickly lose momentum if it doesn’t deliver visible, early value. Without tangible outcomes, questions will surface—is this worth the time, the cost, the disruption? As a leader, your role is to keep the energy high and the progress clear. That starts with sequencing your implementation to deliver early wins that matter. Prioritize the needs of end users, and design your rollout to maximize immediate impact for key stakeholders. Early outcomes are the fuel that keeps transformation moving—they build trust, validate the investment, and give your team the confidence to keep going. Momentum can and should be planned as a business strategy with measurable milestones and successes to fuel the rest of the journey.

Bold Take: Sequence quick wins to show impact to your stakeholders early and keep momentum going

KPIs:

• Adoption Rate of Early Solutions

  • indicates whether early wins are being embraced and used as intended.

• Time-to-Impact for Early Initiatives

  • tracks how quickly teams are moving from concept to execution.

• Number of Early Wins Completed

  • demonstrates momentum and the ability to deliver tangible results early.

The Takeaway

Success in digital transformation projects come from patient and steady investment in people, processes and outcomes. Upgrade your approach with meaningful KPIs and prioritization of data to see results.