2024 Top Struggles in Digital Transformation Initiatives
Change is easy to envision, but hard to implement.
Transformation is a Journey and a Destination
Digital transformation is often misunderstood as a one-and-done initiative—a big project with a start, finish, and a box to check. This mindset is limiting because true transformation is much more dynamic and complex. We’ve all heard the phrase, “It’s a journey, not a destination.” While this wisdom rightly highlights the ongoing nature of transformation, it leaves out a critical truth: there is a destination—a clear goal to achieve.
The destination serves as a north star, providing alignment across teams and ensuring that efforts stay focused on driving tangible outcomes. Without it, transformation can quickly turn into aimless exploration—an endless series of experiments without direction. However, fixating too rigidly on the endpoint can lead to frustration when things inevitably don’t go as planned. That’s where the journey comes into play. Transformation is not a straight line. It’s filled with uncharted paths, lessons learned, and necessary pivots.
This is why agility is paramount. Digital transformation, by its very nature, is about radically changing how things are done. It’s not just about implementing new technologies but fundamentally rethinking processes, workflows, and ways of working. A rigid, waterfall approach rarely works because it assumes you can map out every step in advance. But transformation demands flexibility—adapting to unforeseen challenges, leveraging new opportunities, and continuously improving along the way.
The phrase I often use is, “Set the destination, but focus on the journey.” A defined destination—whether it’s increased operational efficiency, better customer experiences, or enhanced business agility—provides the strategic anchor. It ensures that teams, processes, and investments remain aligned toward a common vision. But the journey requires an agile mindset. It’s about being willing to course-correct, to test and learn, and to recognize that transformation is as much about discovering what works as it is about reaching the goal itself.
𝐂𝐡𝐚𝐧𝐠𝐢𝐧𝐠 𝐒𝐭𝐫𝐮𝐠𝐠𝐥𝐞𝐬
Right now in 2024, according to a LinkedIn study I recently conducted, the top struggle for many companies is WHY (justification and buy-in). And this matches data from WalkMe’s 2024 State of Digital Adoption report, which found that on average 𝟑𝟖% of digital transformation efforts over the last year failed to meet their objectives due to a lack of adoption by end users.” This tells me that most people don’t truly understand the WHY.
Convincing stakeholders and teams of the need for transformation and securing their support is critical. However, this may change from year to year and company to company. Next year, the biggest hurdle might be defining a clear vision or aligning the strategy with real-time feedback and data. Even if you created what was thought of as a clear vision in the past, that may change as you progress, learn more about your own company, the market, competitors, or as technology changes. So what was once clear in the past may need additional clarity again in the future, and that is okay!
𝐇𝐞𝐥𝐩𝐟𝐮𝐥 𝐚𝐝𝐯𝐢𝐜𝐞 𝐫𝐞𝐠𝐚𝐫𝐝𝐥𝐞𝐬𝐬 𝐨𝐟 𝐲𝐨𝐮𝐫 𝐜𝐮𝐫𝐫𝐞𝐧𝐭 𝐬𝐭𝐫𝐮𝐠𝐠𝐥𝐞
What: Defining the Vision
Transformation begins with a clear, compelling vision that serves as the North Star for the organization. Without a shared understanding of what you are aiming to achieve, teams can easily lose direction, creating misalignment and confusion. Start by facilitating workshops with key stakeholders—executives, managers, and frontline teams—to co-create a vision that answers core questions: What problem are we solving? What does success look like? Use a customer-centric approach by incorporating Voice of the Customer (VoC) insights to ensure the vision delivers meaningful value. To make the future state tangible, create visual representations—such as roadmaps, diagrams, or storyboards—that illustrate how the transformation will unfold. Finally, don’t underestimate the power of repetition. Regularly communicate the vision through town halls, internal newsletters, and dashboards so that it stays top-of-mind, reinforcing alignment across all levels of the organization.
How: Crafting the Strategy
Once the vision is set, the challenge becomes how to achieve it. Digital transformation is rarely a straight path; it requires an agile, iterative approach to navigate the inevitable complexities. Break the transformation into manageable phases—plan, build, test, and scale—starting with smaller pilot projects to validate ideas and learn what works. Instead of adhering to a rigid waterfall approach, adopt agile methodologies with sprint-based processes that allow for quick pivots, continuous improvement, and measurable progress. Set specific, incremental milestones with clear KPIs to ensure teams can track progress and celebrate small wins along the way. To remain adaptable, establish robust feedback loops, such as employee surveys, focus groups, or real-time dashboards, that provide insights and allow the strategy to evolve based on real-time results and challenges. By staying flexible and iterative, you can adapt the “how” as new opportunities arise, ensuring steady progress toward the vision.
Why: Securing Justification & Buy-In
The why of transformation is often the biggest hurdle. Without clear justification, gaining buy-in from stakeholders and teams becomes an uphill battle. Start by mapping out your key stakeholders—executives, employees, and customers—and tailoring your message to their priorities. Executives care about ROI, cost savings, and competitive advantage, while employees focus on how the transformation impacts their day-to-day work and growth opportunities. Combine storytelling with data to make the case compelling. For instance, use statistics (like WalkMe’s report showing 38% of transformations fail due to lack of adoption) alongside real-world stories of how transformation can improve outcomes. Identifying and empowering change champions across the organization can further drive buy-in, as peers often inspire greater trust and support. Quick wins are also essential—showing small but tangible results early on demonstrates progress, builds confidence, and strengthens support for larger initiatives.
Where: Prioritizing Initiatives
With so many competing priorities, knowing where to focus first is critical. Start by using an Impact-Effort Matrix to assess initiatives based on their potential impact and the effort required to execute. High-impact, low-effort initiatives should be prioritized first, as they deliver quick value and build momentum. Align each initiative to broader business goals—whether it’s improving operational efficiency, increasing customer satisfaction, or driving revenue growth. Dependencies also matter; sequence projects logically, prioritizing those that enable future initiatives or create foundational improvements. Taking a “start small, scale fast” approach allows organizations to focus efforts on high-potential areas, delivering results early while building the confidence and learnings needed to scale transformation across the organization.
Transformation is a complex process, but tackling the challenges of what, how, why, and where ensures both strategic clarity and operational flexibility. By defining a clear vision, adopting an agile approach, securing strong buy-in, and prioritizing effectively, organizations can navigate the journey successfully while staying focused on their destination. The key lies in balancing direction with adaptability, knowing that each milestone reached brings new opportunities to evolve and improve. Set the destination, embrace the journey, and celebrate progress every step of the way.
References
Jeff Winter LinkedIn Poll 3/3/2024, n=263
Walkme - The State of Digital Adoption 2024: https://www.walkme.com/the-state-of-digital-adoption-2024/
