Three Questions To Ask Before Starting A Digital Transformation Project
Michael Tyrimos is the Founder/CEO of Capacitor Partners, an operations and technology consultancy that transforms large-scale enterprises.
gettyA director walks into a meeting three months into a transformation program and says, “I didn’t know we were doing this.” The consultant presenting the slides goes into a deep state of confusion. The program had already been marked green. What changed?
In another company, halfway through the program, a middle manager stops responding to emails and calls because another priority has taken over. We will revert at some point in the future, they say. When? It remains unknown.
In a workshop, a team member says they do not agree with a change that is meant to impact the entire organization. They do not wish to be part of the project.
If you are someone leading organizational transformation projects, I am certain that the above sounds a bit too familiar. Bain’s 2024 research found that 88% of business transformations fall short of their original ambitions. Situations like these help explain why.
The issue is not the technology itself, but the people and priorities behind it, particularly when key decision-makers were not in the room when the objective was agreed upon. No one sets out to undermine a transformation on day one. The problems emerge months later, quietly, when decisions stall, and teams are not given the backing they need to move forward.
The first question concerns the leadership team. Do the executives and directors share the same understanding of what the transformation involves? A digital transformation is not simply an IT project. It changes how people work, the processes they follow and, only then, the technology that supports that work. I need to hear that shared understanding from more than one person, not only from the sponsor who signed the engagement letter. If a director is surprised by the objective three months into the program, the issue is more than a communication gap. It means their support was never secured, and that can cost the program more than any technical decision.
The second question concerns the people whose day-to-day work will change. Do they understand the vision, the reasoning behind it and what it will mean for them? If I am brought in to lead the technology change before that awareness exists, the program is starting on weak foundations.
McKinsey puts the failure rate for digital transformations at roughly 70% and links a considerable part of that failure to whether the workforce is on board, rather than the technology chosen. When the people doing the work have not been brought along, the program can fail no matter how sound the technical solution is.
Awareness and team “buy-in” to the project matter. Change management models have made the same point for decades. People must first understand why change is happening before anything else can take hold and they want to be part of the change.
The third question is about authority. Who can make binding decisions for the program? The answer cannot be someone who simply attends status meetings or coordinates activity. It must be someone with the mandate to approve trade-offs, reduce scope, unblock a department or overrule a resistant middle manager. If I email that person and do not hear back for three days, it is already a warning sign. Transformations rarely fail because of one major wrong decision. They fail when a hundred smaller, necessary decisions go unmade because no one has the authority to make them.
Research conducted over three years by EY and Saïd Business School at the University of Oxford, and published in 2024, shows why this matters. Almost every transformation reaches what the researchers describe as a moment when the program goes off course and leaders must decide how to respond. They call this “a turning point.” Of the programs surveyed, 96% experienced at least one. Without a named decision-maker to step in at that point, the program can drift.
These questions matter on both sides of the table. For me, they show whether a project is realistic, viable and set up to deliver results, rather than likely to fail before it begins. For everyone on the client side, from the organization to the department and the team, they help protect the investment and, more importantly, the lasting impact the transformation was meant to deliver.
Always keep in mind that leaders who maintain people at the center of the transformation are up to 12 times more likely to improve program performance significantly. That can be the difference between a program that eventually succeeds and one that is eventually abandoned altogether.
Start by questioning the project’s leadership sponsorship, team awareness and point-person authority, before the project even begins.
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