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Digital Transformation Missteps: Analyzing Failures to Forge a Path to Success

Authors: Jenny Magic Jenny Magic
Posted Under: Digital Marketing
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It’s likely that you have one, if not many, marketing innovation projects underway, with deadlines ranging from yesterday (ugh) into the coming year. Whether it’s incorporating AI, leaning into new social media platforms, finally getting serious about content personalization, or a million other possibilities, there’s probably no shortage of priorities on your to-do list.  

As we’ve written about before, there are a ton of roadblocks to digital transformation. It’s not enough to simply have a brilliant strategy. Without the right level of engagement and buy-in from those who will be most affected by the change, even the most meticulously crafted strategies can falter. You can have a comprehensive plan that checks all the boxes and has the full support of company leaders but somehow, a few months after kickoff, the effort has stalled out–either not fully adopted or sometimes not even started.  

Proceeding without employee buy-in is the #1 mistake. 

The often overlooked step that so many organizations skip is building buy-in with the key stakeholders who are going to be impacted by the change. Employees often outwardly agree to a change initiative at a high level, only to resist when it’s time to alter their established routines. This resistance can be subtle and hard to detect, particularly in knowledge work. It’s important to note that these individuals are not intentionally sabotaging the project. Rather, it’s a natural human response to the uncertainty and discomfort that often accompanies change. 

But they’re the ones who can make or break the outcome. Employees can behave in ways that look like work is happening but when there is no genuine partnership, eventually the momentum fails and the plan is scaled back, postponed, or canceled, with much time and effort going to waste. Success depends on understanding and addressing the human element of change. 

Our obsession with productivity is killing our capacity for innovation. 

If leaders are optimizing for full utilization, where employees are busy every minute and there’s no wasted time, there is also zero room in their schedule for new projects. When a change initiative comes up, the limited time employees have to contribute must be spent diving into tasks and action.  

Successful change requires two categories of time investment: time to do the actual tasks and time to plan, build buy-in, detour, brainstorm, gather feedback, calm concerns, quell resistance, reconfigure the plan—all before  actually doing the tasks. Most teams don’t even have the space for the actual change tasks, much less the change planning time. The result is essential employees aren’t committed and the project flounders. But there is a better way. If you take the time to build better buy-in up front, it leads to better change outcomes.  

Effective change can be learned.

Almost none of the visionary leaders we encounter have had any formal training in change management, behavioral psychology, or team performance and motivation as they climbed the corporate ladder. Many otherwise talented leaders are actually ill-equipped to lead transformational change because they excel at leading tasks but are missing the skills to build buy-in. The result of this leadership gap is that key elements are frequently omitted when scoping digital transformation projects.   

Think about the most recent change initiative in your organization and consider if you could easily articulate the following:  

  • The root cause issue that triggered the project 
  • The scope and impact of the project  
  • The change roadmap or plan that considered complexity, competing priorities and timing conflicts 
  • A problem statement that supports requests for the right people, funding, and support 
  • A clear and compelling purpose to boost community and collaboration 
  • A plan for stakeholder communication and engagement in a relevant and targeted way 

If you answered “nope!” you’re not alone. Many organizations try to create certainty by diving into doing. They skip important information gathering and problem agreements before they start collaborating on solutions. 

It can feel tedious to slow down at the beginning of a project and think clearly about desired outcomes and listen to our team, especially when no one has any extra time to contribute. But without this work you might as well not start at all. Research shows that somewhere between 70% and 80% of all change initiatives fail, which likely means if you don’t have time to plan, shelve the idea until you do. And if it’s critical that this gets done now, ask what projects will take a backseat to make realistic space for this project to succeed.  

A vertical roadmap outlining steps to implementing change in organizations. The steps go from top to bottom in the following order: catalyst, capacity, commitment, collaboration, calibration, and calculation.

Build a change roadmap with key elements for adoption built right in. 

A good change roadmap not only outlines the strategic steps to be taken but also considers the human impact of the change. The steps to lay out the roadmap aligns organizational goals with the goals of the stakeholders whose buy-in is critical for project success. This process also ensures the project is considered not in a vacuum but in the context of the entire organization. It’s important to understand the context and capacity before committing to a change initiative. 


What is the problem, who is feeling the pain (and what do they want to do about it), and how urgently does this need to happen? In this phase it’s essential to ensure the visionaries who have identified a strategic gap are aligned and clear on the problem. The milestone for this phase is to understand the context and the root cause of the problem and draft a clear problem statement to socialize with key stakeholders (these are individuals impacted by the change, at all levels of your organization). 


Do we have the capacity to do this now? What happens if we don’t? Here we ask our leaders to pause and consider the strategy in the context of the larger organization. How many team members will be impacted, how motivated are they to support this, and what other constraints or priorities could detract from their ability to successfully see this strategy to completion? The milestone here is a thorough review of how various teams and key stakeholders perceive the problem and their capacity to take on this challenge. 

(Sidebar) What employees won’t tell you 

There are many reasons employees withhold valuable information and perspectives about an upcoming project, including the belief that their feedback will not be taken seriously, a lack of confidence in their ability to clearly articulate their feedback, or concerns about being seen as overly negative or critical.  Whatever the reason, it’s a significant problem for any leader seeking to lead a change initiative. The insights most likely to help your project succeed are locked in the experiences of your employees, and without that information you are making decisions on incomplete information and burying hidden objections.  

It’s your job to make it more rewarding and beneficial for them to provide feedback than to keep it locked inside. A valuable tool at this phase is Confidential Inquiry. 

Outside facilitators get the most honest feedback

As we described in our book, CHANGE FATIGUE, Flip Teams From Burnout to Buy-In, bringing in an objective interviewer to gather employee feedback during a major change project can be a game-changer. Employees often feel more at ease sharing their true feelings and concerns with an outsider, someone who isn’t part of the company hierarchy and has no influence over their job status. This can lead to more honest and open feedback, which is crucial for understanding and addressing employee concerns. It’s like opening a window to let fresh air in – sometimes, it takes an outsider to clear the air and bring new perspectives.  

It can also be valuable to have a fresh pair of eyes on the situation. Change facilitators can ask questions that insiders might not think to ask, and they can spot patterns and trends that may not be apparent to those who are deeply involved in the project. It’s like having a bird’s eye view of the situation – sometimes, you need to step back to see the bigger picture.  

Multiple research studies have found that external facilitators were more effective than internal ones at leading organizational change. The research suggests that this is due to employees’ greater willingness to disclose sensitive information to a trusted outsider, and the external facilitator’s greater freedom to challenge existing norms and routines. 

When it comes to planning organizational change, make sure you use every possible tool to ensure your team shares their true concerns, feedback, and experiences so the project can be adapted early to any red flags their insights might highlight.  


Confirm buy-in from leadership and key stakeholders. Is everyone in agreement on the situation and the plan moving forward? Here we’re looking to all the key leaders to commit to execute whatever the specifics of the strategy require. The milestone here is that resources are allocated, executive sponsors are enthusiastic, and key stakeholders are ready to kick off a collaborative solution process.  


The rest of the change roadmap unfolds based on the collective effort of key stakeholders. This is the “diving into doing” part that so many teams are already good at, pulling together the cross-functional team and starting to map out a solution that meets the objective. When we teach the step-by-step guide to building buy-in for change, the tools and templates focus on the first three steps of the change roadmap process so teams are ready to collaborate effectively.  

You can see that the steps most often skipped (before collaboration begins) are essential groundwork for the eventual adoption of whatever strategy the collaboration creates.  

Successful Digital Transformation Brings Employees Along.

Successful change management is about more than just strategic planning. It’s about understanding and addressing the human element, building a roadmap that considers both the logical and emotional aspects of change, and equipping your stakeholders with the knowledge and skills they need to navigate this journey. By doing so, you can increase the likelihood of your change initiatives being adopted and sustained, leading to lasting improvements in your organization’s performance.  

Implementing new approaches can be challenging. Helping prepare people creates better results for your team and for your customers. If you can set your team up for implementation success, you’ll be more likely to be in that rare 20% to 30% of projects that are actually successful, and you’ll do so while building respect and psychological safety with your team by considering their needs and taking time to build buy-in along the way.  

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