At the growth hacking conference, one slide brought the whole room to silence for three seconds.
It was a stage diagram of digital transformation. Five stages, from “Sensing the Threat” to “Successfully Building a Digital Experience Platform,” drawn clean and tidy, every arrow pointing forward, as if you could arrive simply by following the steps.
Looking at that diagram, what came to mind wasn’t success stories, but corpses.
In more than a decade of consulting and running my own ventures, I’ve seen at least a dozen companies launch digital transformation. The ones that went the full distance? Two. The rest, for the most part, died before stage two—not killed in battle, but bleeding internally, doing themselves in.
If you compare transformation to childbirth, the five stages on that slide are the dilation of the cervix. The problem is: until the dilation is complete and the baby has cried its first breath, nothing counts as success. And most of the companies I’ve seen were already screaming for it to stop when they were barely two fingers dilated.
The First Cut: Shifting Mindsets Equals a Blood Transfusion
The biggest lie in digital transformation is: “Let’s bring in some new tools.”
It’s not a tool problem. It’s a brain problem.
Reading inspirational transformation articles and actually driving change in an organization with live ammunition are two entirely different things. Just as watching a medical documentary doesn’t mean you can perform surgery.
I saw a case once. The owner of a traditional manufacturing business was struck by those four words “digital transformation” at some forum, came back full of ambition, and declared: “We’re going to become a digital enterprise!” And then? He had the IT department buy an ERP system, spent six months implementing it, and the result was that the veteran masters on the floor refused to use it. Because the old master had managed the production line his own way for twenty years, with every parameter living inside his head. Now you want him to enter all of that into an interface he can’t make sense of? His reaction was: “I’ve done it my way for twenty years—is there a problem with the product quality?”
There wasn’t. His methods genuinely worked. The problem is that his methods can’t be scaled, can’t be passed on, can’t be optimized by AI. But how do you tell someone who has done it for twenty years, with consistently good results: “Your methods need to change”?
This is the pain of shifting mindsets. It isn’t as simple as swapping out a system—it’s like a blood transfusion. Replacing type A blood with type B is fatal. And what’s more terrifying: failing to transform quickly won’t make the company collapse immediately. It’s the boiling frog—a slow loss of competitiveness, “imperceptible” to most people. By the time you feel it, it’s usually too late.
The Second Cut: The Desert of Digital Talent
Transformation needs talent. But what kind of talent?
Not engineers who can write code—there are plenty of those on the market. What you need is a rarer species: people who understand the industry, understand the digital world, and also have the managerial capability and political savvy to drive change within an organization.
Just how scarce is this kind of talent? Among everyone I know, the people who possess all three abilities at once number no more than twenty.
Where does the problem lie? Traditional education.
Our education system produces specialists—you understand technology but not business, or you understand business but not technology. To understand both at once, and to understand them well enough to make decisions at the executive level, requires a kind of “never-power-down learning capacity.” But traditional education leads many people to believe that earning a diploma is the endpoint of learning. The result: many people’s knowledge frameworks stopped updating after graduation, but the world didn’t stop and wait for them.
I discussed this problem in “The Super Learner: A Learning Revolution in the Age of AI.” Learning isn’t a one-time event; it’s a system that runs continuously. But in Taiwan’s corporate culture, “learning” is often equated with “attending a training course”—as if finishing the course means you’ve got it, like taking medicine means you’ll get better.
What digital transformation needs isn’t people who have taken courses, but people who live inside a digital mindset. The gap between the two is like the difference between someone who has watched a swimming instructional video and someone who is in the water every day.
The Third Cut: Assassination by the Power Structure
This is the cut that’s least openly discussed, but it’s often the fatal one.
Every digital transformation means a redistribution of power.
A new digital system means more transparent information—data that only a certain department head used to know is now visible to everyone. This is good for the organization, but for that department head, it’s a loss of power. A large part of his value rests on the foundation of “I’m the only one who knows this information.” Now you want to tear down that foundation?
I’ve seen a real case. A company set up a digital innovation team that reported directly to the general manager. The team’s mission was to drive a data-driven decision-making process. Sounds wonderful, right?
The result: the sales department refused to share customer data, on the grounds that “client relationships are sensitive information.” The finance department questioned the new system’s security and demanded a six-month evaluation. The IT department said the new system was incompatible with the existing architecture and required major modifications. The HR department worried that the new process would affect the fairness of employee performance reviews.
Every single objection sounded reasonable. But viewed together, you realize this isn’t a technical problem—it’s a battle to defend power. Vested interests won’t openly oppose transformation (that would be too obvious); they’ll use all kinds of “reasonable concerns” to delay, dilute, and ultimately eliminate any change that threatens their position.
This is what I call “assassination by the power structure.” It’s not a single fatal blow—it’s a slow-acting poison.
The Age of AI: The Same Pit, a Deeper Hole
When I first organized these thoughts in 2019, “digital transformation” was the hottest keyword. Six years later, the keyword has changed to “AI transformation.”
But the underlying problems are exactly the same, if not worse.
Mindset shift? AI demands not merely “learning to use new tools,” but rethinking “what work should be done by humans.” This touches the foundations more deeply than earlier transformations—you’re not just changing how work is done, you’re changing the very definition of work.
Talent scarcity? People who can simultaneously understand the boundaries of AI’s capabilities, industry needs, and organizational politics are even fewer than in the digital transformation era. Because AI’s capabilities are changing rapidly, a judgment made six months ago may be completely outdated six months later. What you need isn’t an expert, but a continuously learning generalist.
Power assassination? AI makes information more transparent, decisions more traceable, performance more quantifiable. This means that those who maintain their position through “information asymmetry” are under even greater threat. Their resistance will be even fiercer.
I felt this profoundly while driving AI adoption in my own company. The greatest resistance was never the technology—technology can always be solved. The greatest resistance is people. It’s the people who feel “AI will make my experience worthless,” the people who worry “if all the data becomes transparent, how do I maintain my authority?”
You Won’t Drop Dead Immediately, but You’ll Slowly Disappear
This is the cruelest part.
Not pursuing digital transformation won’t make your company collapse tomorrow. It will make your company irrelevant five years from now. Just as someone who doesn’t exercise won’t fall ill tomorrow, but ten years later, at the checkup, every number is in the red.
This quality of “chronic death” is precisely transformation’s greatest enemy. Because the human ability to perceive slow change is extremely poor. The frog isn’t unaware that the water is heating up; the rate of heating just happens to fall below its perception threshold.
I’m not sure whether we’re living in the best of times. But I can say with certainty that this is a turbulent and cruel age. It’s not just traditional industries—even the Web 1.0 internet companies that were once disruptors will be cast aside if they refuse to keep evolving.
The advance of the environment is merciless and swift. And the people inside organizations, with their fear and resistance to change, are no different from our ancestors thousands of years ago.
This contradiction is the eternal labor pain of digital transformation. It won’t disappear because technology advances, because the problem was never the technology—the problem is people, and people are the hardest system in the world to upgrade.
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