20 - The Power of Unlearning: Why Great Leaders Let Go to Move Forward

How Senior Leaders Evolve by Releasing Old Assumptions and Adapting to New Realities

Introduction: The Leadership Skill No One Talks About

Every leader knows the importance of learning—staying ahead, adapting to trends, expanding knowledge.

But what’s often overlooked is the equally critical skill of unlearning.

✔ Organizations evolve, but leaders sometimes cling to outdated assumptions that no longer serve them.

✔ Markets shift, but strategies based on past successes can become present limitations.

✔ Teams change, but leadership styles that once worked may now hinder progress.

True leadership growth isn’t just about adding more knowledge—it’s about letting go of ideas, habits, and frameworks that no longer fit.

The strongest leaders don’t just accumulate expertise. They challenge what they already know, refining their approach before reality forces them to.

So how do leaders recognize what needs to be unlearned? And more importantly, how do they make space for new ways of thinking without feeling like they’re abandoning past wisdom?

Step 1: Recognizing When Knowledge Has Become a Limitation

Not everything learned in the past remains relevant, useful, or accurate over time.

A leader who once built success through hands-on control may find that in a growing organization, that same approach now creates bottlenecks.

A company that once dominated through efficiency may struggle in an era where innovation is the real differentiator.

A team that once thrived on a structured hierarchy may find that younger generations expect more autonomy and collaboration.

It’s not that past strategies were wrong—it’s that they belonged to a different era of leadership, and that era has shifted.

How to Identify What Needs to Be Unlearned

Leaders can start by looking for key signals that old ways of thinking are no longer serving them:

1. When a once-successful approach starts producing diminishing returns.

   • A leader who built their career by being the expert in the room may now be limiting their team’s growth by not stepping back.

2. When new behaviors feel uncomfortable—but necessary.

   • A leader used to directing teams with certainty may struggle when employees expect more flexibility and co-creation—but resisting that shift won’t make it disappear.

3. When past experiences are shaping present blind spots.

   • A leader who was burned by a failed risk years ago may now avoid bold moves, even when the conditions have changed.

🔹 Example: When a Leader Had to Unlearn Their Own Strength

A fast-growing startup hired an experienced executive who had led successful transformations at a larger firm. Their structured, data-driven decision-making had worked brilliantly in a stable corporate environment.

But in the startup’s fast-moving, uncertain world, the same rigid frameworks slowed teams down.

At first, they doubled down.

✔ They pushed for more structured processes.

✔ They expected the same predictability they had before.

But results stalled.

Once they recognized that their greatest strength in one context had become a weakness in another, they unlearned their attachment to rigid planning.

✔ They kept their analytical skills but paired them with faster iteration and flexibility.

✔ They stopped over-relying on past experience and started leaning into the company’s present reality.

That pivot—the ability to unlearn, not just apply experience—made them successful in a brand-new environment.

🚦 Leadership Reflection:

• Am I still using a leadership approach that worked in the past but may not fit today?

• Where am I resisting change not because it’s wrong, but because it feels unfamiliar?

• Have I mistaken my experience for a fixed truth rather than a foundation to build upon?

Step 2: Making Space for New Thinking Without Losing Confidence

One reason leaders resist unlearning is that it feels like abandoning expertise—as if letting go of old beliefs means admitting they were wrong.

But unlearning isn’t about erasing the past. It’s about recognizing that knowledge must evolve.

A great leader knows:

✔ Their principles stay constant, but their methods must adapt.

✔ Their experience remains valuable, but it shouldn’t become a barrier to new insights.

How Leaders Make Space for New Thinking

1. Separate identity from expertise.

   • If leadership confidence is based on always being right, unlearning feels like a threat.

   • But when confidence is built on the ability to evolve, unlearning becomes a competitive advantage.

2. Ask more “What if?” questions.

   • Instead of assuming, “This is how it’s done,” shift to:

     • “What if we approached this differently?”

     • “What would someone new to this problem see that I might not?”

3. Surround yourself with diverse perspectives.

   • The more leaders listen to those with different experiences, the easier it becomes to recognize outdated thinking.

   • Staying only in rooms where your perspective is validated is a fast track to stagnation.

🔹 Example: The CEO Who Unlearned Their Approach to Hiring

A CEO prided themselves on hiring based on experience and technical expertise—it had worked for decades.

But as their industry shifted toward innovation and adaptability, they noticed a pattern:

✔ The employees with the most experience weren’t always the ones driving the best results.

✔ The best hires were often those who brought fresh thinking, not just industry tenure.

Rather than defend their long-standing hiring model, they did something rare: they unlearned their old selection criteria.

✔ They expanded recruitment beyond traditional resumes, looking for agility, creativity, and problem-solving over years in the industry.

✔ They adjusted interview processes to reflect future potential, not just past success.

The result? A company that stayed ahead of its industry instead of just maintaining past success.

🚦 Leadership Reflection:

• Am I holding onto outdated processes because they feel familiar?

• Have I built a leadership identity that allows for evolution without insecurity?

• Who challenges my thinking regularly—and do I listen?

Step 3: Reinforcing Unlearning as an Organizational Strength

When leaders make unlearning part of their leadership culture, teams adapt before they have to.

✔ The best organizations don’t just reward execution—they reward insight and adaptation.

✔ They don’t just celebrate what worked—they examine what needs to change next.

How to Create a Culture That Values Unlearning

• Make reflection part of leadership conversations.

  • Instead of just asking, “What’s working?”, also ask, “What assumptions should we question?”

• Reward people for evolving ideas—not just sticking to them.

  • If teams are afraid to change direction, they’ll resist adapting even when needed.

• Create space for experimentation.

  • The best ideas often come from questioning old ones—but that requires a culture where testing new approaches isn’t penalized.

🔹 Example: When Unlearning Became a Competitive Advantage

A company that had dominated its industry for years found that its once predictable customer base was changing.

Instead of relying on historical trends, leadership pushed for:

✔ Real-time listening instead of just past data.

✔ New marketing approaches instead of repeating what worked five years ago.

✔ Agility in product development, adapting faster to consumer shifts.

Because they were willing to unlearn what made them successful in the past, they stayed ahead of competitors who clung to outdated strategies.

🚦 Leadership Reflection:

• Do I lead a company that evolves proactively—or only when forced?

• Where do we need to question long-standing approaches?

• Have we created space for learning and unlearning to coexist?