The head of Risk Management at a major payments business looked across the table at the digital transformation team, during a 2002 meeting, and said: “Digital won’t be a factor in acquiring new customers to our business for ten years.”
The team had the data. They had the customer research. They had a working roadmap. None of it mattered in that room.
Within two years, more than 70% of new accounts were being booked online.
I’ve been in a lot of rooms like that one. The pattern is still the same. The insight is correct. The strategy is sound. And the organization still can’t move. Not because the people are wrong, but because the organization wasn’t built to carry what the strategy required.
That’s the problem nobody wants to name directly. So let me name it.
The rules have changed. The organizations haven’t.
In September 2025, NYU faculty member and academic director Noa Gafni published a piece for the World Economic Forum arguing that Porter’s original Five Forces competitive rivalry, supplier power, buyer power, threat of substitution, barriers to entry were designed for a world that no longer exists. She proposed a new set: technology, climate, societal shifts, economic volatility, and geopolitical pressure.
Her core point: these forces don’t arrive one at a time anymore. They hit simultaneously. What determines whether a company survives them isn’t the quality of its competitive analysis; it’s the ability to navigate all five at once, in real time, without a playbook that covers the combination.
I’d go a step further. The organizations I’ve worked with aren’t struggling because they misread the forces. They’re struggling because they were built for a different game, one where a big strategic challenge arrived, leadership responded, and the organization had time to adapt before the next one landed.
That world is gone. What’s replaced it in tech and fintech especially is relentless simultaneity. AI adoption pressure alongside workforce disruption alongside macroeconomic uncertainty alongside the need to retain talent across five generations with fundamentally different expectations of work. All at once. All the time.
The old rules don’t apply. Most organizations are still running on them.
What the data says and what it doesn’t
The evidence that something structural is broken has been accumulating for years.
Deloitte’s 2025 State of AI in the Enterprise 3,235 leaders surveyed globally found that 37% of organizations are using AI only at a surface level, with little or no actual process change. Despite the investment, the urgency, the board pressure, the headlines. The technology is running. The organization hasn’t changed.
Gartner’s 2024 global survey of over 3,100 CIOs and technology executives found that 52% of digital initiatives fail to meet or exceed intended business outcomes. Across sectors, across budget levels, across leadership teams that knew exactly what they were trying to do.
These aren’t execution failures in the conventional sense. The strategies were right. The technology worked. What failed was the organizational capacity to act on what leadership correctly understood.
The talent data makes the mechanism visible. The World Economic Forum’s Future of Jobs Report 2025 synthesizing responses from over 1,000 global employers representing 14 million workers found that while technical skills top every hiring list, the capabilities differentiating growing organizations from declining ones are resilience, adaptability, and cross-functional agility. Identified as critical. Not hired for with anything like the same discipline.
McKinsey’s 2025 research on digital skill building found that 80% of leaders say upskilling is the right answer to closing capability gaps. Twenty-eight percent plan to actually invest in it. That gap between what leaders say is needed and what they’re willing to resource tells you the problem is understood in the abstract and not yet real enough to fund.
The hiring filter is the tell
Here’s where it gets specific and personal.
When I was building and leading innovation and digital transformation teams, I hired deliberately for diversity of skill and experience. Marketing, analytics, digital, domain knowledge yes. But the thing I cared about most was mindset. Curiosity. Adaptability. A genuine desire to work on something that didn’t have a template yet. Energy for problems that hadn’t been solved before.
What I observed in colleagues taking a different approach came down to two patterns.
The first: “They’ve already done this job.” Presented as risk reduction. But in a transformation context, it’s risk amplification disguised as caution. You’re hiring someone whose primary qualification is that they successfully operated in a different environment one that no longer applies. Pattern recognition is exactly the wrong tool when the pattern has changed.
The second: hiring someone they were “comfortable” with which, if you watched closely, almost always meant someone like them. Same background, same instincts, same frame for what good judgment looks like. The institutional immune system, hiring in its own image.
Neither filter shows up in a job description. But both run through almost every hiring decision in large organizations, quietly ensuring that the people leading transformation efforts were shaped by the very conditions those efforts are trying to change.
I watched a bank’s innovation team spend months building a strategic partnership with a fintech startup a sandbox arrangement that would let them test new commercial concepts without the drag of legacy systems. At the final executive sign-off meeting, the deal died. Cold feet. Multiple objections. Familiar caution dressed up as prudence.
Within two years, that startup exited for $800 million. The bank’s efforts continued to stall.
The people in that room weren’t wrong by the standards of the environment they’d been built for. That’s the point. The environment had changed. The judgment hadn’t.
What “built for this” actually looks like
Technical expertise matters. In fintech especially, domain knowledge is real and not easily substituted. I’m not arguing against it.
What I’m arguing is that technical depth alone in an environment of simultaneous pressure is necessary but not sufficient. Most organizations aren’t making that distinction. They’re hiring for the first condition and hoping the second arrives on its own. It doesn’t. It must be built.
There’s also a trap in the internal versus external hiring decision. Defaulting to internal candidates isn’t wrong; giving your own people opportunity matters for culture. But internal candidates have been shaped by the institutional conditions the transformation is trying to change. That doesn’t disappear because the role has a new title. And when organizations swing hard toward external hiring without building the internal path, they leave resentment behind: the message received by people who weren’t considered is that their experience doesn’t count.
Neither extreme solves the actual problem. The capability profile required for transformation leadership in this environment doesn’t map cleanly onto either the internal talent pool or conventional external search criteria.
What it maps onto: people who can hold a strategic view and a ground-level operational reality at the same time without resolving the tension prematurely. Who treat a “no” in a stakeholder meeting as a signal worth decoding. Who know how to run a genuine experiment with honest success criteria and real tolerance for a result that redirects the work rather than a staged proof of concept designed to confirm what leadership already decided.
These aren’t personality traits. They’re capabilities. Learnable, developable, and entirely absent from most job descriptions for transformation roles.
The question worth sitting with
Noa Gafni’s New Five Forces describe what your organization is being asked to navigate. The organizational conditions you’ve built including who you hire and what you actually select for determine whether navigation is possible.
Think about the last person your organization put in charge of a transformation effort. Not what the job description said. What actually drove the decision to put that specific person in that specific role.
If the honest answer is some version of “they’d done something like this before” or “leadership was comfortable with them” your organization just optimized for the last environment, not the one you’re in now.
The forces are not going to slow down. The organizations that close this gap first will have an advantage that compounds. The ones that don’t will keep funding strategies their organizations were never built to carry.
Amy Radin is a strategic advisor, keynote speaker, and NYU Adjunct Instructor, Entrepreneurship and Management, focused on why transformation succeeds or stalls in large, complex organizations. Drawing on senior leadership roles at Citi, American Express, and AXA, including one of the world’s first corporate Chief Innovation Officer roles, she helps leaders build the capabilities required to absorb, scale, and sustain change. Learn more at amyradin.com.