Your Team Uses AI Daily. Are you? Or are You becoming irrelevant?
Why the executives who delegate AI adoption will share the fate of Generation Wang. And how to avoid becoming a digital fossil in your own company.
The most dangerous phrase in executive leadership today is five words long: “It’s not for me, it’s for my team.”
I’ve heard this sentence several dozen times in the past six months.
Always from executives over 45.
Always delivered with the serene confidence of someone who believes they’ve found the optimal delegation strategy. And always, without exception, from leaders who are actively engineering their own obsolescence.
We’ve seen this before.
The year was 2009.
The 2009 Playbook Nobody Remembers
Forbes and Google partnered on a whitepaper called “The Rise of the Digital C-Suite.” They surveyed hundreds of executives on how they adapted to the internet, mobile, and search. The findings split leadership into two camps that predicted career trajectories for the next fifteen years.
The losers were “Generation Wang.”
Executives over 50 who treated the internet as a task to be delegated. Forty percent never used their mobile devices for work.
They operated on summaries prepared by others.
Because they never saw raw information, they couldn’t question flawed assumptions. Their refusal to adapt went from a status symbol to a sign of incompetence within five years.
The winners were “Generation Netscape.”
Fifty-one percent preferred to locate information themselves.
Thirty-five percent used their mobile daily for work.
They understood that using Google wasn’t a petty work for their secretary.
It was strategic skill build out.
The pattern is repeating.
Except this time, the consequences arrive faster and cut deeper.
The Knowledge Inversion Problem
Harvard Business School researchers discovered something uncomfortable about AI’s impact on organizations. Erik Brynjolfsson found that AI raises the performance of new workers dramatically, closing the gap between junior and senior outputs almost instantly.
Read that again.
Your 25-year-old analyst with 18 months of experience can now produce work that previously required a decade of pattern recognition.
The knowledge hierarchy that justified your salary premium?
AI just compressed it into a prompt.
But here’s what nobody tells you at board dinners: the knowledge isn’t disappearing.
It’s inverting.
Your team learns the tool’s nuances daily. They discover which prompts generate quality output and which produce hallucinations. They know when the model struggles with revenue recognition versus when it excels at market analysis.
You don’t know any of this.
You can’t.
Because you’re not in the trenches with the tools.
The knowledge flows upward.
The org chart doesn’t move.
You can no longer mentor people on the primary lever of their work because they understand it better than you do.
The Judgment Collapse
Here’s where the trap closes.
You occasionally use AI for your tasks. Maybe drafting a speech or summarizing a report. You discover the frontier for your occasional use cases. But your team works with these tools eight hours daily on specialized problems you’ve never attempted.
When they estimate a project will take three weeks with AI assistance, how do you evaluate that claim? When they say the model can’t handle a particular analysis, how do you know if that’s a technical limitation or a knowledge gap? When they recommend a tool for €50,000, what mental model validates that investment?
You’re making judgment calls about capabilities you’ve never tested.
The METR study from 2025 made this embarrassingly concrete.
Experienced developers working on familiar codebases estimated AI increased their productivity by 20%. Objective measurement showed a 19% decrease. The developers themselves couldn’t tell whether the tools were helping or hurting.
A 40-percentage-point gap between perception and reality.
Among experts.
Working with AI tools daily.
Now imagine you’re a CEO evaluating AI investments based on demos and executive summaries. You’re not just blind. You’re confidently blind.
Delegation Blindness: The Terminal Condition
The consultant term for this is “Delegation Blindness”: the trap where outsourcing hands-on work creates exactly the information gap that makes coordination impossible.
Every function Gen AI touches is experiencing this pattern. Media companies need operators who can distinguish a real technical constraint on Meta from a padded timeline. Finance teams need leaders who understand which analysis the model nails versus which it confidently fabricates. Operations executives need the pattern recognition to know when an AI recommendation is architecturally sound versus superficially plausible.
People who never log into the platforms can’t ask the right questions.
I’ve built and rebuilt dozens of companies over last two decades.
The executives who thrive through technology transitions share one characteristic: they use the tools themselves, early, and often.
Not because they’ll become power users.
Because strategic judgment requires calibrated intuition about capabilities and limitations. And it allows You for proper educated guess.
You cannot outsource the development of that intuition.
The Personal Transformation Imperative
Most AI transformation programs miss the point entirely.
They focus on organizational change: new workflows, new tools, new team structures.
They treat executives as sponsors and budget approvers rather than practitioners.
This is precisely backwards.
Organizational transformation follows personal transformation.
Always has.
An executive who personally understands AI’s jagged frontier, where it handles tasks brilliantly and where it fails spectacularly, makes fundamentally different strategic decisions than one operating on summaries and vendor presentations.
The difference shows up in three places: resource allocation accuracy, risk assessment calibration, and speed of strategic adjustment.
Executives with hands-on AI fluency catch problems 3-6 months earlier.
They avoid the €2-5 million write-offs that plague organizations where leadership delegates understanding to subordinates.
This isn’t about becoming a prompt engineer.
It’s about developing Frontier Fluency: the calibrated sense of where AI boundaries sit that you only get by bumping into them yourself.
The AI Executive Transformation Program
I designed a program specifically for this problem.
One intensive day in Prague or San Francisco followed by 90 days of advisory engagement (aka call me any time from any time zone, I will pick it up:) .
Maximum six C-level executives per cohort.
The workshop isn’t theory.
It’s about deployment.
First, personal advisory systems and RAG on executives data.
Then, followed by examples of what I helped to built in past three years in AI space, tailored for each executive.
By 18:00 on day one, every executive has a personal AI advisory system built on RAG and multi-agent workflows, calibrated to their company’s products, customers, and competitive landscape.
They build autonomous agents for email management, meeting preparation, and real-time analytical support.
They experience the jagged frontier firsthand.
Succeeding brilliantly at tasks that look hard and failing embarrassingly at tasks that look easy.
The 90-day advisory phase transforms one-day exposure into permanent capability.
Weekly deployment milestones.
Measurable automation targets.
Direct access to practitioners who’ve implemented these AI systems across 50+ organizations.
The numbers from our cohorts: 78% AI deployment rate versus 23% for committee-driven initiatives. Autonomous product team models reducing annual labor costs by 60%. Small cross-functional teams of approximately 4.5 FTE delivering AI capabilities that previously required 20-person departments.
The €15,000 transformation workshop investment returns multiples within first 30 days.
Not through organizational efficiency, but through the strategic clarity that comes from personal understanding.
The Fork in the Road
Generation Wang executives convinced themselves that delegation was wisdom.
They believed their value was strategic thinking untainted by operational detail.
They were wrong, and the market corrected them within five years when they went out of the market.
You’re facing the same fork.
The executives who personally master AI capabilities will make better investment decisions, catch implementation problems earlier, and maintain strategic relevance as the technology reshapes every function they oversee.
The executives who delegate AI understanding to their teams will gradually lose the ability to evaluate what those teams tell them.
The gap is already opening.
It compounds monthly.
In 2009, the winners were Generation Netscape. Executives who understood that using Google wasn’t secretarial, it was strategic. In 2025 and beyond, the winners will be executives who understand that using AI isn’t technical, it’s existential.
The question isn’t whether AI will transform your industry.
It will.
The question is whether you’ll understand that transformation from the inside.
Or learn about it from the summary your replacement writes.
The AI Executive Transformation Program runs quarterly in Prague and San Francisco. Six seats maximum. Details available upon request at jf@dcxps.com .