Four Things Leaders Must Get Right to Make Digital Transformation Actually Work
- Aug 24
- 9 min read
Written by Dr. Jessica Herbert, PCC, Executive Coach
Dr. Jessica Herbert, PCC, has held every seat: investigator, cyber manager, data scientist, academic, nationwide consultant, and executive coach across 36 states, 100+ communities, and four countries. She writes about leadership, people, and technology from the inside, never from theory. Proven. Not Promised.
Many organizations do not fail at purchasing technology; they fail at the subsequent digital transformation activities: how the workflow changes, whether staff have the skills to adjust and perform with the new technology, and whether there is documentation to help train new staff. These failures don’t happen at once.
They occur in a handful of quiet decisions made months earlier: who was put on the project team, who was still on it by phase three, which leaders were told this one was not theirs to own, and whether anyone funded the work of teaching people how the job itself was about to change. Those four decisions belong to leadership.
What is digital transformation?
Digital transformation involves the integration of technology or digital tools into how an organization operates and delivers its services. Inherently, the adoption of technology and tools transforms processes, culture, and customer experience. The Columbia University Press description of David L. Rogers’s The Digital Transformation Roadmap similarly emphasizes that digital transformation requires organizational change, not simply new technology.
Digital transformation is not the purchase of a system or tool itself. It is a change to how work gets done: who does it, in what order, with what documentation, under what policy, reviewed by whom, and measured how. The software or hardware is the visible part. The workflow, the policy, the approval path, and the quiet redistribution of expertise are the actual change.
I watched this play out in a local government office replacing its records management system. Leadership described it, honestly and in good faith, as a technology upgrade. But staff were not simply learning new screens. The way information was entered changed. The report narrative standards changed. Supervisory review steps changed. How quality assurance audits were conducted changed. How information was shared with other stakeholders changed. Three months after the system went live, the office had a beautiful system and a workforce quietly maintaining a shadow process on the side because the new way had never been explained as a way of working, only as a tool.
When the tool didn’t work, staff created workarounds.
Why the odds are what they are
The numbers on this are not encouraging, and they are worth sitting with. Boston Consulting Group analyzed 70 BCG-supported digital transformations alongside a survey of 825 senior executives and found that only 30% of digital transformations met or exceeded their target value and resulted in sustainable change. The rest either created some value without meeting their targets or produced limited value without sustainable change.
Two findings inside that research matter more than the headline number. The first: only one in four organizations cleared BCG’s threshold for deploying high-caliber talent. The second: three out of four executives believed they had good leadership engagement. Only one in three actually had committed engagement from middle management, the people whose buy-in determines whether anything survives contact with the floor.
The distance between believing you are aligned and being aligned is where transformations go to die.
Here is the part that should encourage you. The same research found that organizations addressing all six of its success factors could move their odds of success from about 30% to more than 80%. That is not a rounding error. That is the difference between hoping and playing to win, and the four priorities below are the ones squarely inside a leader’s control.
What are four decisions that determine success?
1. Staff the team on fit and strength, not rank and role
The default is assignment by organizational chart. Whoever holds the seat, whoever has the rank, whoever is available. It feels fair. It is also the single fastest way to put a capable person in a role that will exhaust them.
Transformation work rewards two very different profiles. Some people are energized by ambiguity. They generate options, tolerate unfinished things, and move comfortably before the picture is clear. Others are energized by structure. They build the process, write the documentation, close the gaps, and make a thing repeatable. Both are indispensable. Neither is more valuable. They are simply not needed at the same moment, and they are rarely productive in the same room at the same stage.
I worked with an agency that put its commander with the strongest process discipline in charge of the discovery phase. He was excellent: meticulous, respected, thorough. The group spent four months exhaustively documenting the current state and never got to imagining the future one. That was not a competence failure. It was a fit failure, and the leader who made the assignment could not see it because he was staffing by reputation rather than by strength.
At Asbatra Coaching, we use the Predictive Index to map behavioral drives across a project team, so a leader can look at a phase and ask a better question than "who is available?" The Predictive Index describes its Behavioral Assessment as measuring natural behavioral drives and needs and provides tools for mapping behavioral strengths and needs across teams. The better question is: what does this specific phase demand, and who on my bench is built for it?
There is a compounding effect here that leaders consistently underestimate. People placed inside their strengths do not just perform better; they generate energy that others catch. Put three people in their sweet spot on a project team and the meeting changes character. That is the contagion you want running through a transformation.
2. Change the roster when the project changes phase
This is the one leaders resist, and I understand why. In most organizations, being moved off a project reads as a demotion. So leaders leave people in place long past the point of usefulness, and the person who was brilliant in discovery grinds themselves down through eighteen months of implementation detail they were never built for.
Build your success from the start. Announce that this is a phased assignment, that the roster is designed to change, and that rotating off is a completion, not a removal. When you name it in advance, the rotation stops carrying stigma and starts carrying credibility. Then honor it: hold a real handoff, and give public credit to the person leaving as they leave.
Public safety leaders should find this familiar. Specialty assignments occur based on perceived strengths and abilities. The rotation into an assignment is acknowledged as beneficial, but the rotation out is often unclear or not articulated. Rotation out of these assignments happens for many reasons: to prevent burnout, to build organizational depth, and to keep the work fresh. Transformation projects deserve the same discipline and for the same reasons.
The secondary benefit is bench strength. Every rotation moves transformation literacy into another part of the organization. By the end of a well-phased project, you have not just a new system. You have two dozen people who understand how change actually gets made here.
3. Align the entire leadership table, not just the sponsor
The most common alignment failure I see is also the most understandable. The division or unit that owns the project engages. Everyone else waits their turn and sometimes even criticizes from afar.
The logic seems sound. It is not my system, not my phase, not my budget line. But true digital transformation does not stay in one lane. It reaches and impacts all parts of an organization, whether as the doer, receiver, manager, or budget justifier, just at different times. When a leader taps out because it is not theirs yet, two things happen. Their people arrive at their phase with no preparation, and the leader has to perform a fluency they never built. Both are avoidable.
This is precisely the middle management gap in the BCG data, and it is the reason so many executives are surprised to learn their alignment was thinner than it looked. BCG found that three out of four executives felt they had good leadership engagement, while only one in three had committed middle management engagement.
What alignment actually requires is more specific than a briefing:
Articulate, division by division, what changes for them and roughly when, even if their phase is nine months out. Vague timelines are not kindness; they are a deferral of preparation.
Put leaders who do not own the project in the strategic checkpoints, not just the status updates. Being in the room where tradeoffs get made is what builds ownership.
Make the transformation a standing item on the leadership agenda rather than a periodic project report. Standing items signal permanence. Project reports signal that this will pass.
Know that engagement travels. When a leader in one division asks substantive questions in a transformation meeting, their supervisors start asking substantive questions too. Disengagement travels exactly the same way, just faster.
4. Fund the reskilling, not only the technology
Look at almost any transformation budget and you will find the same line items. Licensing, implementation, hardware, vendor support, contingency. Then, somewhere near the bottom and often added late, a modest line for training, usually meaning a series of demonstrations of the new tool. That budget is built for a software installation. It is not built for a change in how people work.
The scale of the need is well documented. The World Economic Forum’s Future of Jobs Report 2025 found that employers expect 39% of workers’ core skills to change by 2030. Its findings also indicate that 59 out of every 100 workers are expected to need training by 2030, while 63% of surveyed employers identify skills gaps as the biggest barrier to business transformation. Above culture. Above capital. Above regulation.
Here is the encouraging part, and it comes from Paul Leonardi and Tsedal Neeley’s work in The Digital Mindset. Their thirty percent rule suggests that people do not need mastery to be genuinely effective with technology; they need roughly 30% fluency. Leonardi compares this with learning a language, where about four thousand words can provide working competence compared with roughly twelve thousand for mastery. Nobody on your team needs to become a data scientist. They need enough fluency to ask good questions, spot when something looks wrong, and use the new workflow with confidence.
Thirty percent is a target you can budget, schedule, and measure. That is a far more useful goal than "training."
One more thing, and it is where most training plans fall short: be specific about what is changing beyond the tool. Which policy is different? Which documentation standard is different? Which approval now routes elsewhere? People do not circumvent new systems out of stubbornness. They circumvent them when the reasoning was never made clear and the old way still works well enough to get through the shift.
Five moves to make in the next thirty days if you are planning for digital transformation
Map the phases and staff them separately. Write down what each phase actually demands: divergent thinking, process discipline, stakeholder negotiation. Then name people to phases rather than to the project as a whole.
Say the rotation out loud at kickoff. One sentence, in front of everyone, establishing that the roster is designed to change and that rotating off is completion, not removal.
Put every division head on the record. Ask each one to state what changes for their people and approximately when. The ones who cannot answer have just shown you where your alignment gap is.
Fund the thirty percent. Separate the training budget into tool fluency, workflow change, and policy change, and protect the time for people to actually use it.
Define what "done" looks like for people, not just for the system. Adoption, proficiency, and the retirement of the shadow process, not the launch date.
None of these five necessarily requires new technology, though several require leaders to dedicate time and resources. They require leaders to make decisions centered on people with the same rigor they already apply to vendor selection.
The part worth remembering
Every transformation I have watched succeed had the same underlying quality, and it was never the sophistication of the platform. It was that leadership treated its people as the strategy rather than as the thing the strategy would be done to.
You are not managing a system implementation. You are asking a workforce to change how it does the work it built its professional identity around. Staff that intentionally. Rotate people before they break. Keep the whole leadership table in the room. Pay for the learning.
Do those four things and you are not hoping to land in the 30%. You are playing to win.
Call to action
If you are in the middle of one of these projects right now, or about to be, I write about the human side of organizational change every week in Leading Through Change. Subscribe and you will get the frameworks, the failure patterns, and the questions worth asking before your next phase begins.
Read more from Dr. Jessica Herbert, PCC
Dr. Jessica Herbert, PCC, Executive Coach
Dr. Jessica Herbert, PCC, has spent 27 years at the intersection of public safety, data analytics, and organizational change, not as a theorist, but as the detective in the networks, the orchestrator behind the analytical team, the scientist building the models, and the consultant and coach leading change across 36 states and 100+ communities in the United States. She is the founder of IDEA Analytics and Asbatra Coaching, companies that bring leadership, people, and technology together to find their path to high performance. Her work is built on a simple conviction: data helps us think and behave differently, but lasting change requires transforming both the system and the people running it.
