Learning to Lead Again (And Again and Again): The Myth of Certainty

Good leaders never stop learning. Great leaders, the kind who leave a positive lasting impact not just on organizations, but on people’s lives, go a step further: they learn, unlearn, and relearn, over and over again.

Learning is only part of the equation. Unlearning, releasing long-held beliefs, updating outdated assumptions, and facing our own blind spots, requires something more: humility.

Courage. And a deep commitment to being changed by what we hear, see, and experience.

I once worked with a client, let’s call him David, who came to coaching after being promoted to a senior leadership role in a fast-growing technology enterprise. He was smart, successful, and deeply committed to the mission. But within the first few sessions, it became clear that something wasn’t working. His team was disengaged. Feedback loops were closed.

And he felt stuck, frustrated by what he saw as a lack of initiative and drive from those around him.

When we slowed things down and created space for reflection, a deeper truth began to surface. David had always believed that a “strong leader” was decisive, composed, and above all, in control. That showing vulnerability, or even uncertainty, would undermine his credibility. It’s what he had modelled from mentors earlier in his career, and it had served him well, until it didn’t.

Through our coaching conversations, David began to unearth some of the stories he was carrying. That asking for help meant weakness. That slowing down meant inefficiency. That being liked and being respected were in constant conflict.

As we explored these beliefs, I gently asked, “What if leadership isn't about holding everything together, but letting some things fall apart so something better can emerge?”

That question opened something. Slowly, David began to test new ways of leading, starting with listening more, asking instead of telling, and naming uncertainty in team meetings.

It wasn’t comfortable. It brought up fear, resistance, and even grief for the identity he was letting go of. But he kept showing up.

One of the hardest lessons David learned was this: unlearning also means stepping into situations without knowing how they’ll end. 

There are no guarantees that things will go smoothly. No perfect playbook. The outcome may not be a textbook success, and that’s part of the work. So much of what keeps us stuck in old patterns is the illusion that control creates safety. That if we do it “right,” we’ll avoid discomfort, failure, or loss.

But real leadership lives in the space beyond that illusion. In uncertainty. In courage without a script.

One day, after facilitating a difficult team conversation where emotions were raw and real, David said something I’ll never forget:

“For the first time, I wasn’t the one with the answers, and somehow, I feel more trusted than ever.”

That moment marked a shift. Not just in his leadership style, but in who he was willing to become.

Unlearning is not about being wrong.

It’s about being willing to be changed, by what we hear, what we see, and what we allow ourselves to feel. It requires humility. It takes courage. And it asks us to walk forward without guarantees, trusting that growth and meaning often emerge from the very places we once feared.

The Real Work Begins with Listening

We often celebrate growth mindset, lifelong learning, and curiosity in leadership, and rightly so. Research by Carol Dweck shows that people who adopt a growth mindset are more resilient and open to new challenges. In today’s fast-changing world, this mindset is essential.

But the deeper work of leadership begins with listening, not just as a communication skill, but as a way of being.

In Dare to Lead, Brené Brown writes:

“Leaders must either invest a reasonable amount of time attending to fears and feelings, or squander an unreasonable amount of time trying to manage ineffective and unproductive behavior.”

Listening is how we attend. It’s how we show up, curious rather than certain, present rather than reactive.

Women leaders like Jacinda Ardern, Ngozi Okonjo-Iweala, and Michelle Obama have modeled this kind of presence. They listen for what’s spoken and unspoken, holding space for complexity and humanity.

Ardern’s empathetic leadership through crises reflected what many now call transformational presence, a leadership style grounded in connection, clarity, and care.

As adrienne maree brown reminds us in Emergent Strategy:

“The first and most vital step in practicing radical honesty is learning to listen—deeply, actively, with your whole being.”

Listening is not passive. It is a radical act of humility. And it opens the door to the hardest part of leadership: unlearning.

The Courage to Unlearn

To unlearn is to admit: I was wrong.

To say: I didn’t know. To change course when new truths emerge.

Organizational psychologist Adam Grant captures this in Think Again:

“The purpose of learning isn't to affirm our beliefs; it’s to evolve them.”

Unlearning challenges the ego. It invites leaders to let go of identities tied to being the expert or the one with the answers. It requires what Grant calls confident humility, being secure enough to acknowledge our limitations and wise enough to seek input, especially from those with different lived experiences.

Unlearning is especially important in social impact and equity work.

It’s where leaders must confront unconscious biases, decolonize systems, and embrace different truths. And it is never comfortable. That’s the point.

This idea, that leadership isn’t about being right, but about being responsible, is one that transformational leaders embody. And it demands constant unlearning.

The Leadership Superpowers: Adaptability and Resilience

When you commit to listening and unlearning, the natural next step is building adaptability, the ability to stay flexible in the face of change, and resilience, the capacity to recover and grow through adversity.

These aren’t just personality traits. They are skills that can be cultivated.

The World Economic Forum lists adaptability and resilience among the top 10 most important skills for the future of work. McKinsey has similarly emphasized that leaders who can pivot quickly, learn continuously, and respond empathetically will be best positioned to guide their organizations through uncertainty.

Adaptable leaders understand that complexity is not a threat, it’s a signal that the old playbook no longer applies. Resilient leaders see failure as feedback, not finality.

They bounce forward, not just back.

Obama, in his conversation with Brené Brown, spoke about facing challenges that were “impossible in some way”, where the solution wasn’t about solving a problem, but navigating tension, holding paradox.

He said many of the problems he faced as President weren’t problems with solutions, but polarities, contradictory truths that had to be held simultaneously.

Leading through them required the strength to act and the humility to know he might not get it all right.

“Sometimes you’re not choosing between good and bad—you’re choosing between bad and worse,” he said. “And you have to live with the trade-offs.”

This is where leadership maturity shows up: in the ability to stay grounded in your values while moving forward without certainty. To act without needing to be perfect. To acknowledge that some tensions will always exist, and to lead anyway.

Shedding Old Identities: The Shift in Power, Inclusion, and the Myth of Certainty

Consider the shift many leaders have had to make around power and inclusion. Concepts like psychological safety, racial equity, and trauma-informed leadership are not just buzzwords, they are reshaping the foundations of how leadership is defined and practiced.

To truly embrace these frameworks means shedding not only outdated policies, but entire identities built around control, authority, or infallibility. The image of the all-knowing, all-powerful leader, detached from emotion, certain in opinion, and sole bearer of truth, is not just outdated. It’s dangerous.

In a world that’s more connected and complex than ever before, the idea that one person’s singular perspective is superior to all others is not only false, it’s a complete illusion.

Yet, this illusion persists, particularly in political leadership across the globe. Nobel laureate and journalist Maria Ressa underscores this point, highlighting how modern authoritarians manipulate information to consolidate power:

“When you want to rip the heart out of a democracy, you go after the facts. That’s what modern authoritarians do.”

Ressa's observation reveals that authoritarian leaders often distort or suppress facts to maintain the facade of infallibility, misleading the public into believing in their sole authority. This manipulation underscores the critical need for diverse perspectives and collaborative leadership in today's intricate global landscape.

From Hungary to Russia, North Korea to Nicaragua, the concentration of power in the hands of authoritarian figures persists, often relying on fear, disinformation, and the suppression of dissent. But these systems are built on fragile foundations. They resist collaboration. They fear vulnerability.

And they crumble when faced with the collective power of people who know better, who know that lasting change doesn’t come from dominance, but from dialogue, courage, and shared wisdom.

By contrast, in organizations and communities around the world, a very different kind of leadership is emerging. One that recognizes that leading in today’s world isn’t about having all the answers, it’s about creating space for many voices to be heard.

It’s about facilitating wisdom, not hoarding it.

Psychological safety, a concept developed by Harvard Business School professor Amy Edmondson, is now widely recognized as a top predictor of high-performing teams. When people feel safe to speak up, to challenge, to share a dissenting opinion, they innovate. They grow. They trust.

And to foster psychological safety, leaders must unlearn old scripts:

• That authority is more important than empathy

• That control is more effective than collaboration

• That power is zero-sum

  
  

Trauma-informed leadership asks even more of us. It requires an awareness that people bring invisible pain into workplaces, grief, marginalization, systemic oppression, intergenerational trauma. Leaders who are trauma-informed don’t pathologize this pain; they hold space for healing without needing to fix or deny it.

They lead with compassion, consistency, and boundaries, not with dominance or bravado.

Racial equity and inclusion, too, require deep unlearning, especially for those who’ve benefited from systems of privilege. True equity work means giving up comfort, superiority, and the myth of neutrality.

It means listening across difference, acknowledging harm, and actively working to redistribute power.

The Inner Work of Transformational Leadership

At its heart, transformational leadership is about being willing to change, internally and externally, in the pursuit of a better future.

It’s the leader who listens with their whole self, unlearns with grace, and adapts with integrity who transforms not just their organization, but the people within it.

This is the kind of leadership the world is calling for:

• More humility than ego

• More listening than talking

• More courage to change than comfort in staying the same

  
  

And it starts with one conversation, one moment of honesty, one brave act of letting go.

An Invitation to Lead Differently

If you’ve made it this far, you’re likely someone who senses that leadership, real leadership, asks more of us than ever before. You understand that humility, listening, and unlearning are not signs of weakness, but the very foundation of strength in a changing world.

If you’re on this path, redefining how you show up, shifting old patterns, navigating complexity, I’d love to walk alongside you.

As a leadership coach, I work with change-makers, emerging and seasoned leaders, and soulful disruptors who are ready to lead from a deeper place.

Together, we explore the inner work of leadership, unlock clarity in the face of uncertainty, and cultivate the courage to lead in a way that’s true to you.

If that resonates, I invite you to book a free consultation or reach out to start a conversation.

Because you don’t have to figure it all out alone. And the world needs your kind of leadership, now more than ever.

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Hi, I’m Monika, Strengths Coach and facilitator. I help individuals and groups cultivate resilience, emotional intelligence, and well-being through strengths-based coaching. Passionate about transformative and creative leadership, I empower leaders to drive meaningful change within themselves, their organizations, and beyond.

I hope you’ll visit often, and I look forward to connecting and working together!