Take the Red Pill: The Leadership Choice to Unlearn
You feel it, don’t you? That persistent glitch in your leadership operating system.
It happens in quiet moments - when your perfectly crafted quarterly plan hits reality and crumbles. When your team’s velocity mysteriously drops despite following the same runbook that guaranteed success just 18 months ago. When you find yourself saying “this always worked before” more than you’d like to admit.
Welcome to your Matrix moment. (btw, a proudly Warner Bros. Discovery movie)
Just like Neo’s world of green code and artificial reality, we’re all living inside a system - a leadership Matrix built on pre-AI assumptions. The strategies, mental models, and “proven” approaches that made us successful are the very code holding us back from seeing what’s actually happening.
The most dangerous leaders today aren’t those who lack skills. They’re the ones trapped in their own success, convinced that mastery of the old system is their greatest asset. They don’t realize it’s become their biggest liability.
The Choice: Blue Pill or Red Pill?
Remember Morpheus’s offer to Neo?
“You take the blue pill—the story ends, you wake up in your bed and believe whatever you want to believe. You take the red pill—you stay in Wonderland, and I show you how deep the rabbit hole goes.”
For leaders in the AI era, the blue pill is seductive. It’s the belief that you can simply layer AI tools onto your existing workflows. That prompt engineering is just another skill to add to your toolkit. That the fundamental rules of strategy, execution, and team dynamics remain unchanged.
The red pill? It’s accepting that AI demands you unlearn your most fundamental assumptions about work itself.
This isn’t passive forgetting - that’s just decay. Unlearning is an active, conscious choice to dismantle your old worldview to see the new reality clearly. It’s the deliberate abandonment of a comfortable paradigm for a more powerful truth.
Most leaders are choosing the blue pill without realizing it.
The Architect’s Trap: When Success Becomes Your Prison
In The Matrix, the Architect explains that the system works precisely because its inhabitants are comfortable with predictable rules. Our past successes have become the “code” of our comfortable leadership prison.
This is what I call the AI-Era Competency Trap. Your “Dominant Logic” - the mental models that led to your success - was programmed for a world where:
Data analysis: weeks → hours with AI agents
Strategic insights: analyst armies → instant via AI BI
Competitive moats: lasted years → erode in months
ML deployments: 6-month sprints → days with MLOps
Data governance: quarterly audits → real-time enforcement
AI use cases: narrow tasks → enterprise-wide transformation
AI makes this old code catastrophically obsolete.
Yet we cling to our expertise in the old system because our identity as “masters” is tied up in it. The act of unplugging feels like admitting failure, creating massive psychological resistance to the very changes needed to survive.
Consider this -
If an AI agent can produce a 90% complete market analysis in two hours, what does that do to your assumption that “thorough analysis takes two weeks”?
If LLMs can generate first drafts that rival human output, what happens to your belief that “quality content requires extensive human craft”?
The trap springs when we mistake our mastery of an obsolete system for mastery itself.
Building Your Leadership Dojo - Unlearning
Remember Neo’s training in the dojo? “You think that’s air you’re breathing now?” It was a safe space to fail, to unlearn the physics of the old world and rewire his brain for the new reality.
As leaders, we need to create this same kind of dojo for ourselves and our teams - a space with high psychological safety to unlearn old habits and build AI-native ones.
Step 1: “See the Code” (Make Old Rules Visible)
You can’t break rules you can’t see. Most of our operating assumptions are invisible, running like background code in our leadership operating system.
Run this exercise with your team: “What are three core assumptions about our work that were absolutely true five years ago?” Write them down. Examples might be:
“A competitive analysis requires human analysts”
“Quality customer research takes months to complete”
“Strategic planning is a quarterly exercise”
This makes the invisible code explicit. Only then can you begin to question it.
Step 2: “The Jump Program” (Run AI-Native Experiments)
Morpheus knew Neo had to fail to learn. Neo couldn’t just think his way to new abilities - he had to experience the new reality.
Pick one assumption from Step 1 and design a small experiment that uses AI to completely obliterate it. For example:
Old assumption: “Market research takes our team six weeks”
AI experiment: “What if we use AI agents to gather competitive intelligence, analyze customer feedback, and identify market gaps in six hours? What new opportunities does that speed unlock?”
Start small. Run time-boxed experiments. Measure not just efficiency gains, but what entirely new possibilities emerge when the constraint disappears.
Step 3: “There Is No Spoon” (Formalize Dissent)
The spoon only bends when Neo unlearns his belief in its reality. The biggest breakthroughs come when we realize our perceived limitations are self-imposed constructs.
Implement “Red Team“ exercises where a team’s job is to argue for the most radical, AI-first approach to a challenge. Their mission: force everyone to confront the possibility that their “spoons” - their perceived limitations - don’t actually exist.
Ask questions like:
“What if this process could be 10x faster?”
“What if we had perfect information instead of making this decision with incomplete data?”
“What if our customers could get this outcome instantly?”
These exercises reveal how many of our constraints are legacy thinking, not real barriers.
Now, What Unlearning Actually Unlocks
Here’s what I’ve discovered through my own unlearning journey: the goal isn’t to become anti-expertise. It’s to become meta-expert - skilled at rapidly developing new expertise as contexts change.
When you successfully unlearn old models, you unlock:
Strategic Velocity: You can move from insight to action in days, not quarters, because you’re not trapped in slow, legacy decision-making processes.
Competitive Advantage: While competitors cling to old playbooks, you’re operating with fundamentally different assumptions about what’s possible.
Team Empowerment: When you model unlearning, you give your team permission to challenge sacred cows and propose radical solutions.
Innovation Capacity: Unlearning creates cognitive space for genuinely new ideas instead of incremental improvements to old approaches.
Your Red Pill Moment Starts Now
The AI revolution isn’t coming - it’s here. Leaders who cling to old rules will become Agents, desperately fighting to maintain a system that’s already crumbling. Those who have the courage to unlearn and guide their teams out of the old Matrix will build the future.
This is your red pill moment.
The question isn’t whether you’ll need to unlearn - it’s whether you’ll choose to do it proactively, with intention and strategy, or whether reality will force it on you when your old models finally, catastrophically fail.
Your First Step: Identify one “unbreakable rule” from your pre-AI leadership operation system. Something you’ve never questioned because it’s always worked. Now ask yourself:
“If AI could eliminate the constraint that created this rule, what becomes possible?”
The rabbit hole goes deeper than you think. But on the other side? A kind of leadership leverage that previous generations could never imagine.
Welcome to Wonderland.
What’s the first assumption you’re willing to unlearn this week? I’d love to hear your thoughts.