Tory EvansDigital Transformation Keeps Failing for the Same Boring Reason
March 14, 2026
I want to be very clear about something before we get into this: I am not a pessimist. I believe in change. I believe in reinvention. I believe in the human capacity to build something new out of the rubble of something broken. I send a 6am motivational text every single morning from the parking garage of my old office building because the wifi still reaches and frankly the routine keeps me grounded. Optimism is a practice.
But even I - a man who has reframed every major loss in his life as a "growth corridor" - cannot look at the data on digital transformation and feel anything other than deep, exasperated frustration at an industry that refuses to learn the same lesson for the tenth year running.
Here is the lesson. Are you ready? The technology is not the problem. It never was.
The Numbers Are Embarrassing at This Point
Research from Boston Consulting Group and McKinsey consistently shows that 70% of digital transformation initiatives fail to meet their objectives - and Bain's 2024 analysis reveals that 88% of business transformations fail to achieve their original ambitions. Not 88% of bad ones. Not 88% of underfunded startups. 88% across the board. That's not a failure rate. That's a demolition rate.
We've collectively achieved something remarkable: burning through the IDC-reported $2.3 trillion while the failure rate stays stubbornly above 70%. By 2026, global spend on digital transformation is projected to reach $3.4 trillion, and based on current trajectory, most of it won't work either. We are collectively, as a business community, setting money on fire at industrial scale and calling it innovation.
Failed transformations cost organizations an average of 12% of annual revenue through wasted investment and opportunity costs. Twelve percent. That is not a rounding error. That is a line item that should end careers. And somehow, very few careers actually end over it.
What makes this especially maddening is that these numbers have barely moved in a decade. Digital transformation has been a top priority for enterprises for over a decade, yet the failure rate remains around 70%. The technology has changed. The budgets have grown. The consultants have multiplied. And the failure rate just sits there, nodding at us, completely unbothered.
The Boring, Preventable, Totally Obvious Reason
The thing that kills me is that the reason is so well-documented that there is no excuse for being surprised by it anymore.
Most projects stumble due to people-centric issues - unclear vision, poor process, lack of user adoption, and cultural resistance - rather than the technology itself.
That's it. That's the thing. It's the people.
Not the software. Not the budget. Not the vendor. Not the CTO who was "brought on to lead this." Digital transformation isn't a technology problem - it's about understanding how people actually work, not how we think they should work. One CIO put it very plainly: "Money rarely solves these problems. I've seen $50 million projects fail while $500,000 initiatives transform entire departments. The difference? Understanding the human element before touching the technology."
Derek came into the office last quarter with a fifteen-slide deck about how we needed to "completely overhaul" our client onboarding flow. New tools, new automations, new everything. I asked him if he'd talked to the three people who actually do onboarding about what slows them down. He had not. The deck was very good, though. Very thorough. There was a slide with a timeline graphic that I genuinely admired.
That is digital transformation in miniature.
GE, Ford, and the Art of Very Expensive Lessons
The corporate graveyard for this stuff is enormous and well-documented, and I think it's worth sitting in it for a moment because these are not small companies making rookie mistakes.
General Electric spent billions on GE Digital in 2015 to exploit data and become a tech powerhouse. The unit quickly got stuck chasing short-term goals instead of long-term innovative results. GE tried too many things without focusing on any specific area. They eventually retreated from their digital ambitions in 2018 with a loss of $22 billion. Twenty-two billion dollars. Gone. Because nobody stopped to ask whether the organization was actually ready to operate as a software company before they started spending like one.
Ford launched Ford Smart Mobility in 2014 to build digitally enabled cars with better mobility. The project failed mainly because it didn't connect with the rest of the company - it sat in a different location and worked like a separate business with no ties to other units. That is the summary. They built the transformation in a separate building and then wondered why the rest of Ford didn't feel transformed. Ford's strategic pivot to a "mobility company" faltered due to cultural and operational misalignment. Despite acquisitions and bold messaging, its internal systems and workforce were not prepared to operate as a tech-driven service business.
And then there's the BBC's Digital Media Initiative. The BBC's Digital Media Initiative lost over £100 million because "it lacked a shared vision between stakeholders and never showed how the new system would benefit different departments." A hundred million pounds. Vanished. Because different departments couldn't agree on what "good" looked like.
I'm not telling you this to be grim. I'm telling you this because these are billion-dollar organizations with armies of advisors, and they all tripped over the same wire. Not the technology. Not the budget. The people in the room who never got a shared definition of what success actually looked like - and the leaders who were too busy announcing the transformation to bother building one.
Why Everyone Keeps Skipping the Hard Part
Here is my actual theory, and I've thought about this a lot in parking garages and late-night coffee shops and also once during a coaching session where Chris very gently asked me if I was doing okay and I said I was doing great and then we spent forty-five minutes talking through it and it turned into a really productive session for both of us.
The reason companies keep skipping the people side is because the people side is slow, uncomfortable, and impossible to put in a press release.
You can announce a $50 million Salesforce implementation. You can publish a case study about your new cloud architecture. You cannot write a press release that says "We spent 18 months having honest conversations with our middle managers about why they feel threatened by automation and we're starting to make progress." The incentive structure rewards the announcement of transformation, not the execution of it.
Leadership announces bold visions. Departments reorganise. Dashboards get redesigned. And yet, core workflows remain untouched, or worse, are layered with additional complexity. This is transformation-washing - the organizational equivalent of repainting a house that has mold in the walls.
Pouring modern technology over bad processes is a recipe for failure. If you don't fix underlying processes and workflows first, technology will just accelerate existing inefficiencies. For example, automating a chaotic manual process without standardizing it will simply produce chaos faster.
Stephanie sat in on a vendor demo last month for a very expensive automation platform and kept asking about the ROI timeline. The vendor said eighteen months. She said that seemed long. She has never once had to wait eighteen months for anything. I love her but she is not the person you want making go/no-go decisions on change management timelines.
What Actually Works (And Why Companies Resist It)
The data on what actually works is not exciting. It is not a new platform. It is not an AI layer bolted on top of your existing stack. It is, annoyingly, the most human thing possible.
Prosci's global research found that projects with excellent change management are seven times more likely to meet or exceed objectives compared to those with poor change management. Seven times. These are not marginal improvements. These are transformational multipliers. And they come from investing in people and communication, not in new tooling.
Two-thirds of strong transformers ensured people assigned to transformations had at least half their time allocated to the new role. Half their time. Not a Friday afternoon. Not a shared Slack channel. Actual dedicated headcount, protected from other demands, focused on making the change land properly.
I've watched businesses do software rollouts where the "training" is a 20-minute Loom video and a PDF. I once trialed a CRM during a particularly difficult week - I was managing three active clients, sleeping four hours a night, and running on gas station coffee - and I genuinely could not figure out the pipeline view for two days because the onboarding assumed I had time to explore. I did not have time to explore. Most of your employees do not have time to explore. That is the normal human condition of a working person inside a company that is also trying to hit quarterly targets. If you want to understand how tools actually land at the ground level, the CRM space is a case study in the gap between demo-day promise and live-use reality.
Organizations average 897 applications but only 29% are integrated. MuleSoft's 2025 Connectivity Benchmark reveals massive integration gaps creating data silos. You can add a new platform. You can run a pilot. But if it doesn't connect to the systems people already live in, it will become another island. Another thing people use in parallel with the old thing. Another thing that quietly fails to transform anything.
The companies that get this right tend to treat transformation the way a good coach treats a client in crisis - you don't start with the goal, you start with where they actually are. You build something small that works before you build something big that looks good in a deck. This is also exactly how good project management is supposed to work, and yet somehow organizations that know this intellectually still launch enterprise-wide rollouts on an eighteen-month timeline with a single go-live date and then act surprised when it collapses under its own weight.
The AI Question Nobody Wants to Answer Honestly
Here is where I will say something that will make the vendor community uncomfortable: the current wave of AI-led digital transformation is on track to fail for exactly the same reasons. Different technology, identical mistake.
Most companies approach digital transformation like renovating a kitchen while the family's still cooking dinner. They bolt AI onto antiquated processes, implement cloud solutions without reimagining workflows, then wonder why productivity plummets and employees revolt.
The AI rebrand is happening at speed right now and I have written about it before. The pattern is familiar: announce the initiative, buy the platform, underfund the change management, be confused by adoption rates at month nine. When a company's response to transformation failure is to embrace the latest technology before existing efforts have clearly proven their success or failure, the result is that they end up with many half-implemented ideas and their personnel get fatigued.
Change fatigue is real and it compounds. Employees are asked to abandon established routines, often with little context or clarity. Years of top-down change initiatives have left teams skeptical, leading to passive disengagement. When change fatigue sets in, even the most promising tools fall flat.
If you want to know which tools are worth betting on during this cycle - and I say this as someone who has trialed a lot of them at 11pm from a laptop in a parking structure - the ones that reduce friction in the first five minutes matter more than the ones with the best feature set at month three. Employee training platforms are having a real moment right now specifically because someone finally figured out that software rollouts without embedded learning are just expensive frustrations.
What I Actually Think Is Going to Happen
I think the failure rate is going to stay stubbornly high for another five to seven years. I think spending will increase. I think the press releases will remain optimistic. I think the real story will continue to be buried in the retrospectives that nobody reads.
And I think the companies that break the pattern won't be the ones with the biggest transformation budgets. They'll be the ones where a mid-level manager had enough political cover to slow the rollout down, run a real pilot, actually listen to the people doing the work, and build something that stuck. They won't get a conference keynote. They'll just quietly have a team that uses the thing they bought.
Jamie - and I say this with genuine respect for his effort - came in last week with a fully built strategy document for how we should "digitally transform our internal communications." It was sixty-two pages. The font was beautiful. He had surveyed no one. Linda read three pages and said Gerald had once been on a transformation project at his company and the whole thing fell apart after eight months and they ended up going back to spreadsheets. Jamie said that wouldn't happen here. Linda smiled and said she hoped not.
I hope not either. But the data suggests we should be more worried about the process than the platform. The reason this keeps happening is not that companies are dumb or cheap or lazy. It's that the hard work - the slow, underfunded, un-press-releasable work of actually bringing people along - has no champion. Until it does, the expensive costumes will keep collecting dust in the corner.
The wifi in the parking garage is very good, by the way. I have had some of my clearest thinking here. Sometimes the right environment for transformation is just wherever you actually are, not wherever you planned to be.