3 Critical Blockers to Transformation Success

After decades in the technology industry, I’ve learned that digital transformation isn’t just a buzzword—it’s a matter of survival for most organizations. But more than 60% of digital transformation efforts fail. It’s not faulty technology that does them in. What usually happens is that organizations consistently stumble over the same few blockers. 

The good news is, these blockers are entirely avoidable. We’ve experienced our share of setbacks and successes, and we’re passionate about helping others navigate this complex landscape. Let’s break down these blockers and chart a course for more consistent digital transformation success.

Blocker 1: Lack of a Clear North Star Outcome

Many organizations dive into digital transformation without a clear destination. They get lost in a sea of technical requirements and deliverables, losing sight of the “why” behind their efforts. It’s like setting sail without a compass—you’re moving, but are you really getting anywhere?

A clearly defined, measurable outcome—a North Star—is essential for aligning teams, focusing resources, and achieving success. This North Star should be:

• • Tangible and measurable
  • Aligned with broader business goals
  • Understood and embraced by all key stakeholders

For instance, when we worked with a large federal agency, the North Star was crystal clear: replace a legacy system that posed significant cybersecurity risks and hindered modernization. With one of our large financial services clients, the goal was to close five specific FDIC audit gaps that were stifling growth. In both cases, having a clear North Star provided the focus and direction needed to drive transformation.

Once defined, your North Star outcome becomes the foundation of your transformation efforts, guiding all organizational communication, setting a clear and unifying expectation across every level of the organization. 

Without a North Star, projects may seem successful on paper, but fail to deliver meaningful business impact, and stakeholders become disillusioned as they struggle to see the value of their investments. This misalignment can create a ripple effect, causing future transformation initiatives to be met with skepticism or resistance. Moreover, without a clear North Star, you’re more susceptible to “scope creep” and endless customizations that deviate from your core objectives.

How to Overcome It: 

The first step is to gather your key stakeholders for a facilitated session to unearth the fundamental “why” behind your transformation efforts. Consider enlisting a neutral third-party facilitator to lead this discussion. An external perspective can help mitigate internal biases and foster more open, honest dialogue.

Begin by creating a secure environment where participants feel safe to voice their thoughts candidly. This trust-building exercise is crucial before diving into the tough questions. Once you’ve established this foundation, probe deeper: What keeps you up at night? What would make this investment a game-changer for your organization?

As you refine your ideas, continuously challenge them with questions like “So what?” and “Who cares?” This process helps distill your North Star into a clear, impactful one-sentence statement. Remember, this exercise requires skill and experience to navigate effectively. If the prospect seems daunting given the personalities in your organization, don’t hesitate to seek expert help.

Your North Star should be so clear and compelling that everyone from the C-suite to the front lines can articulate it. In fact, it should be so simple that you could explain the business outcome to your partner at home, without any prior IT knowledge. Remember, if your outcome sounds like “implement XYZ software,” you’re still lost at sea. The clearer and more relatable your North Star, the more effectively it will guide your transformation journey.

Blocker 2: Underestimating the Human Element

It’s easy to get seduced by the allure of new technology, but remember: technology alone doesn’t produce outcomes—people do. If you don’t invest in change management, training, and driving user adoption, your transformation efforts will fall flat.

Think about your smartphone. What percentage of its features do you actually use? Most people only scratch the surface. The same is true for enterprise technology. 

Without proper communication and enablement, low adoption rates will undermine the entire transformation effort, regardless of how cutting-edge your solution is. You may find pockets of resistance throughout the organization, with employees reverting to old processes or creating workarounds. 

This not only diminishes the return on your technology investment but can also lead to deteriorating customer and employee experiences, putting your professional credibility on the line. Once you lose momentum, it’s incredibly difficult to regain. Remember, if you lose people from the outset, it’s an uphill battle to turn things around. While technology can often be fixed, poor communication isn’t so easily mended.

How to Overcome It:

Start by identifying key stakeholders early in the project and understanding their unique needs. Then, launch targeted, multi-channel communications tailored to different audiences. Focus on explaining why the change is happening, what’s in it for them personally, and how it will benefit the organization. Use a variety of formats like town halls, email campaigns, and open house events to create awareness and drive adoption throughout the project lifecycle.

At one federal agency, we created over 450 pieces of communication in 18 months across various projects. This level of engagement was crucial for driving adoption and ultimately achieving the desired outcomes. They reached 80% adoption of their self-service portal in ServiceNow.

But you can’t just talk at people—you have to engage them. Create feedback loops that make employees feel heard. Host “innovation jams” where staff can brainstorm ways to leverage the new technology. And remember, training isn’t a one-and-done deal. Create a continuous learning environment with refresher courses, peer-to-peer coaching, and easily accessible resources. Your goal is to make the new way of working so intuitive and beneficial that going back to the old way feels unthinkable.

Blocker 3: The ‘Project Completion’ Mindset

It’s tempting to draw up a finish line as soon as you start a transformation project. But digital transformation is an ongoing journey of evolution and improvement. If you don’t plan for continuous change and innovation, you’ll quickly lose momentum and fall behind.

Imagine a train that’s been stuck in one place for years. You invest enormous effort to get it moving again, only to immediately cut the fuel supply once it starts rolling. That’s what happens when organizations view transformation as a one-time project rather than an ongoing capability.

Without the right mindset, you risk falling into the “implement and forget” trap. Initial gains may quickly plateau or even regress as the organization fails to keep pace with evolving needs and technologies. This stagnation can lead to a widening gap between your capabilities and market demands. You may find yourself in a cycle of large, disruptive overhauls every few years, rather than benefiting from continuous, manageable improvements.

How to Overcome It:

Start by establishing a “transformation taskforce”—a cross-functional team charged with keeping the momentum going long after the initial project wraps up. Empower them with resources and executive support to continually identify and implement improvements.  Ensure that you have the appropriate leadership, architecture, development, and communications capabilities budgeted into your O&M function. If not, it will feel like the momentum has slowed or stopped, in which case, we have lost credibility, and it is hard to get it back.

Next, bake adaptability into your infrastructure. This might mean adopting modular systems that can be easily updated or creating APIs that allow for seamless integration of new technologies. The goal is to build a flexible foundation that can evolve with your needs.

Finally, shift your budgeting mindset. Instead of allocating all your resources upfront, create an “innovation fund” for ongoing enhancements. This sends a powerful message that transformation is a journey, not a destination. It also allows you to quickly capitalize on new opportunities or address emerging challenges without getting bogged down in bureaucracy.

The Path Forward

As you embark on or continue your transformation journey, keep these key principles in mind: start with a clear, measurable North Star outcome. Invest heavily in the human side of change. And build for continuous evolution, not one-time implementation.

Digital transformation is challenging, but with the right approach, it’s also incredibly rewarding. By avoiding these common pitfalls, you can position your organization to thrive in the digital age. The journey may be complex, but with a clear vision, a focus on people, and a commitment to ongoing innovation, you can navigate the path to digital transformation success.