As a successful leader, your experience has likely made you rich in insight but poor in adaptability. What got you here won’t get you there, and “there” is coming at an exponential speed. So here’s the hard truth: your legacy is now your liability.

Your Legacy Is Now Your Liability

Artificial intelligence isn’t just a technology shift, it’s a leadership reckoning. It’s not about using ChatGPT to write memos faster. It’s about fundamentally changing how decisions are made, problems are framed, and value is created.

The uncomfortable truth? The biggest barrier to AI transformation in your company is you. Or more precisely: what you believe, but no longer question.

What Is Unlearning?

Unlearning isn’t forgetting. It’s not removing, or discarding your knowledge or experience. It’s the conscious act to let go of outdated mindsets and behaviors that were once successful, but are now limiting your success. In my book Unlearn: Let Go of Past Success to Achieve Extraordinary Results, I delve deeper into why embracing unlearning is essential for modern leaders.

It’s a decision to recognize outdated information and actively engage in taking in new information to inform effective decision making and action. It’s to update your mindset and behavior to better match today’s realities.

“Unlearning is the missing competency of modern leadership.”
— Barry O’Reilly, Unlearn: Let Go of Past Success to Achieve Extraordinary Results

Unlearning is how high performers continue to perform in changing contexts. It’s what enabled Satya Nadella to pivot Microsoft from a fortress of products to a platform of possibilities. It’s how Jensen Huang reimagined NVIDIA, not as a chipmaker, but as the engine room of an AI-driven world.

And now, it’s your turn.

Why Unlearning Matters More Than Ever

Because we’re entering an era where hardcoded experience can become a liability. Where the frameworks that once worked, such as your favorite MBA strategy decks, agile transformation blueprints, and maturity models are actively harmful.

AI punishes rigidity. It rewards curiosity. It renders the “command-and-control” leader obsolete.

In this new landscape:

  • Strategy isn’t set annually, it’s simulated daily.
  • The best decisions don’t come from the top, they emerge from data and real-time customer insights.
  • Learning isn’t hierarchical, it’s continuous, collective, and machine-accelerated.

Unlearning is no longer a nice-to-have. It’s the differentiator between legacy leaders and future-fit ones.

7 Things You Must Unlearn to Lead with AI

1. “Expertise means having the answers.”

Wrong. Leadership now means asking better questions.

In an AI-first world, the best leaders don’t know everything. They know how to frame the problem, tune the system, and let data speak. Teach your team to experiment, not comply.

In fact, my leading indicator for leadership isn’t the quality of the answers, it is the quality of the questions they ask. Limited questions is a tell for legacy leadership.

2. “Success is scaling what works.”

This logic worked in the industrial age. But with AI, what worked in one area today might be obsolete tomorrow, or unfit for the entire organization.

You must scale your ability to test, learn, and adapt.

Build systems that learn faster than your competitors do. You’re no longer optimizing efficiency, you’re optimizing intelligence and adaptability to new information.

3. “Humans tell machines what to do.”

In traditional programming, this made sense. With AI, you no longer script behavior, you shape outcomes, monitor results, and provide more context to tune.

Your job is to teach, not tell.

You train the machine on what good looks like, provide context, and curate feedback loops. That’s leadership by design, not instruction.

4. “Data is an output.”

Most organizations see data as exhaust, like a car, and something collected after action. With AI, data is the fuel.

Your strategy must generate and leverage data at every touchpoint.

If you don’t know how to turn your workflows into learning loops, your competitors will. Always ask, “How are we learning from this action? How are we using that insight to make our machine smarter?”

5. “IT owns AI.”

If AI lives only in your tech team, you’ve already lost.

AI is a leadership capability.

Product, marketing, finance; everyone must understand how to harness machine intelligence. You don’t need to code, but you do need to lead AI-literate teams.

We’ve seen this most in our AI Executive Coaching Program. Over 75% of participants are not IT leaders but Executives, VPs and Department leaders looking for a structured approach for them to learn AI tools, tactics and traits to role model change in their companies and for their teams.

6. “Culture is the soft stuff.”

Culture is actually your organization’s machine learning model.

It’s the accumulated shared learning of your people: how they perceive, decide, and behave.

Audit your success metrics, incentives, and rituals.

If your culture rewards predictability over learning, it will sabotage your AI ambition. If your culture only recognizes success, speed without experimentation, failures and adaptability no one will ever unlearn, or try anything new.

7. “Transformation is about tools.”

Nope.

Transformation is about unlearning.

Tools follow Traits, and Tasks for the New Era of Decision-Making. If your people are randomly playing with all the new tools each week, you won’t make progress, and will be overwhelmed. Start with the mindset and behaviors you need, the tasks you sense are most important, then explore tools last—not first.

Machines Unlearn, Too

Here’s the irony: even machines now need to unlearn.

Modern AI systems are being trained not just to learn from data, but to selectively forget, to remove biased, outdated, or incorrect information. It’s called machine unlearning, and it’s becoming critical for responsible AI.

If the systems we build need to unlearn to remain effective, why should humans be exempt?

“Your unlearning rate must exceed your irrelevance rate.”
— Barry O’Reilly, Unlearn: Let Go of Past Success to Achieve Extraordinary Results

Leading in the Age of AI: 5 Provocations

1. Your MBA might be killing your AI strategy. You learned to optimize stable systems. AI means exploring uncertainty with excellence.
2. If your AI strategy doesn’t scare you, it’s not ambitious enough. Safe pilots = slow death.
3. If you outsource your AI learning to consultants, you’re not leading, you’re delegating your future.
4. Unlearning is a team sport. Build rituals that reward curiosity, not conformity.
5. The cost of experimentation is near-zero. The cost of stagnation is existential.

The Unlearn Leadership Playbook (Starter Moves)

Want to lead in this new era? Start here:

  • What behavior do you feel is holding you back most with AI?
  • What mindset shift would you like to see in yourself regarding AI?
  • Identify a work habit and ask yourself, what could I unlearn here?
  • Host an “Unlearning Lab” with your leadership team. What assumptions are we operating under that no longer hold?
  • Assign AI exploration goals not to your tech team, but to your business leaders.
  • Read your own success metrics like an AI model would. What are you optimizing for? Are those outcomes still valid?

Unlearn Starts with You

You can’t lead transformation from the sidelines.
You can’t lead AI if you’re afraid to look obsolete.
You can’t scale learning if you’re clinging to knowing.

This is your invitation to step out of your comfort zone, into curiosity.

The leaders who thrive in the age of AI won’t be the most technical.

They’ll be the most adaptable.
The most curious.
The most willing to unlearn.

Ready to Unlearn?

This is the defining leadership skill of the next decade. If you’re serious about staying relevant, competitive, and impactful:

Start your unlearning journey with me.

Or reach out for a keynote, workshop, or executive advisory session.
Because your legacy doesn’t have to be your liability.

It can be the launchpad for your reinvention.