For years, businesses have talked about “digital transformation” as though digital were a destination.
Move to the cloud. Modernize the ERP. Get serious about data. Automate some processes. Add AI. Check enough boxes, and eventually the organization would emerge on the other side transformed.
There’s just one problem: There is no other side anymore.
Technology is changing too quickly, customer expectations are moving too quickly, and artificial intelligence is rewriting the possibilities too quickly for transformation to remain something an organization periodically undertakes.
Russell Kern, longtime entrepreneur, marketer, and former CEO of KERN, put it particularly well during a recent conversation with Jason Cohen on On the Right Stack.
“I want to get rid of the word digital,” Kern said, “and just talk about organizational transformation at the speed of the world.”
Kern writes regularly about marketing, leadership, and transformation at russellkern.com.
That distinction matters.
The transformation project has become a permanent condition
The traditional model of transformation assumes a relatively stable starting point and an identifiable destination. Organizations assess where they are, determine where they need to go, implement the necessary technology and processes, manage the change, and move forward.
That model is increasingly mismatched with reality.
Deloitte’s 2026 Global Human Capital Trends research found that 85 percent of respondents consider developing the ability of organizations and workers to adapt at today’s required speed critical, but only 7 percent believe their organizations are leading at it. Perhaps more tellingly, just 27 percent believe their organizations manage change effectively.
That suggests the competitive advantage isn’t simply adopting the next technology. It is developing an organization capable of continually adapting to whatever comes next.
Kern described the questions leaders should be asking themselves differently: What are we reinventing? What are we reevaluating? What should we stop, start, and experiment with?
Those aren’t questions for a three-year transformation roadmap. They are questions organizations increasingly need to ask continuously.
AI is a power tool, not a replacement for judgment
Nowhere is this tension more apparent than with artificial intelligence.
Kern compares AI to the power tools in his garage. For creative people, data professionals, and business leaders, he sees AI as an extraordinarily powerful new tool—one capable of expanding our thinking, accelerating analysis, and presenting possibilities we may not have generated ourselves.
But a power tool still needs an operator.
Kern warned about what he called the “addiction and seduction” of AI output: its speed and apparent authority can make it remarkably easy to accept an answer without challenging it. His prescription is decidedly human: pause, reflect, review, and question the output before accepting it.
That’s an important distinction for businesses racing to incorporate AI. The objective isn’t to remove human judgment from the process. It’s to make human judgment more capable.
As Kern told Jason, use AI as a “creative partner” and a “collaboration partner,” but don’t surrender human intuition in the process.
Your workforce may be the real AI infrastructure
Companies are spending enormous amounts of time evaluating AI platforms, models, data architecture, and use cases. Kern believes many executives are overlooking something more fundamental: whether their people are prepared to use any of it.
When Jason asked what executives aren’t paying enough attention to, Kern’s answer was immediate: “The training of their workforce.”
Recent research suggests that concern is well founded.
McKinsey reports that while 75 percent of U.S. workers expect AI to change their roles within five years, only 45 percent have recently participated in an upskilling program. The World Economic Forum similarly identifies expanding upskilling and reskilling as one of three major workforce priorities as organizations move from AI experimentation toward implementation.
And this isn’t simply about sending employees to an AI seminar.
Leaders themselves need to use the tools, understand what they can and cannot do, experience their limitations, and model responsible adoption. Kern’s advice to executives was wonderfully uncomplicated: “Train yourself, use the tools, feel the pain, feel the joy, feel the risks,” and then cascade that knowledge through the organization.
That’s a very different approach from announcing an AI initiative from the executive suite.
Technology doesn’t fix an organization that can’t make decisions
There was another theme running through the conversation that may be even more important.
Technology amplifies organizational capability. It doesn’t create it.
If an organization doesn’t have clear decision governance, if departments endlessly debate ownership, if data remains fragmented or insecure, or if teams cannot collaborate effectively, another technology investment isn’t going to magically resolve those problems.
Kern was unequivocal on this point: “I don’t care what technology you have.”
What matters is whether the infrastructure, governance, data, security, and people around that technology can harness its power—and whether what ultimately reaches the customer actually solves a problem.
That may be particularly important as organizations move deeper into AI. Deloitte’s 2026 research similarly finds that many enterprises have moved beyond asking whether to adopt AI, but relatively few have made the corresponding changes to how work is designed, how autonomy is governed, and how value is measured.
Buying technology is relatively easy.
Changing how an organization behaves is much harder.
That gap—between buying technology and changing how an organization behaves—is where advisory work earns its keep. It’s the problem Right Stack Advisors helps leaders work through: aligning governance, data, and people so technology investments actually land.
Transformation starts with people
Toward the end of their conversation, Jason asked Kern the question he asks every On the Right Stack guest: If CEOs, CIOs, entrepreneurs, and business leaders remembered only one thing from the discussion, what should it be?
After more than 30 minutes discussing data, AI, customer centricity, technology, entrepreneurship, and leadership, Kern didn’t mention a platform, an algorithm, or even artificial intelligence.
“The power of their team comes from structure, governance, and practice.”
That’s the shift. Transformation was never really about the technology—it was always about building an organization that can keep changing after the technology does. The tools will keep arriving. The work is making sure your people, your governance, and your decisions are ready to use them.
That’s the work Right Stack Advisors does with leaders—and it’s the thread running through every episode of On the Right Stack.
Listen to the full conversation with Russell Kern.
Ready to build an organization that can keep changing? Talk to the Right Stack team.