Hello colleagues,

Welcome back to our series on The Leadership Practices Worth Talking About.

In the first newsletter in this series, we explored how celebration and radical hospitality create the relational foundation for thriving school communities.

Today, we're diving into something that makes many school leaders uncomfortable:

What I’ve come to believe in my second decade of leading a school is that vulnerability in leadership isn't about oversharing or becoming an emotional mess in faculty meetings

It's about showing up as a whole human being—growth edges and all—in ways that build trust, model courage, and give permission for your entire community to grow.

It is being honest with yourself and with others about your own humanity as a leader

Here, then, is the second “Leadership Practice Worth Talking About”

Here's what most of us learned about leadership (at least, this is what I learned watching leaders from my own experience):

Leaders project confidence. They have all the answers. They never sweat or break

So we put on the mask of the all-knowing principal. The unshakeable superintendent. The leader who's got it all under control.

And I get it. That mask feels safe. It feels professional.

But here's what I've learned in my experience

That mask limits our effectiveness.

And it prevents us from being the leaders our schools actually need.

Because real leadership—the kind that changes lives and transforms cultures—isn't about maintaining the appearance of having it all together.

Real leadership involves difficult choices. It involves risk. It involves navigating uncertainty.

My first year in leadership taught me that viscerally.

In my third month as the Head of School, I faced a serious situation that ended up involving the board and the police, a situation that required me to check my ego at the door.

I knew I had two choices:

Try to handle this on my own or seek wise counsel from those who had been in the role much longer than I had been

Thankfully, I chose the latter and reached out to a cohort of school leaders I trusted and respected to seek their advice and wisdom.

That vulnerability, that ability to say “I need help” even as the top leader in my school, probably saved me more than even I realize.

What I have found out the hard way in two decades of school leaders is this:

Leadership isn’t about my ego

It is about being worthy of being followed

Management is about keeping things running smoothly. Maintaining efficiency. Ensuring the bills are paid and systems are functioning well.

Leadership is something else altogether.

Leaders carry the weight of the vision and values in their bones

Leadership, as Chrisopher Hodgkinson writes, "is the cultivation of purpose—yours first, then others”

It's not just about building a resume or climbing the ladder.

It’s about bearing the weight so others can flourish

This means that, unlike the manager, the leader is one who grieves, who weeps, who watches as others fall away and facets of the vision held as essential fade off.

Leaders suffer the "dark night of the soul" as part of the process. They have endured some stuff

Managers work a j-o-b. They clock in and out; they collect their paycheck and go home.

Leaders, on the other hand, spend their very lives on something that has cost them everything. They have burnt the ships. They are all in. Their blood is spilt; you can put your fingers in their wounds.

And that level of leadership requires a significant amount of strategic vulnerability

To lead with that level of depth, of commitment, of sacrifice requires a high level of strategic vulnerability.

There is perhaps no one better writing today on the power and urgency of strategic vulnerability than Dr. Brené Brown

Brené Brown's decades of research have fundamentally reshaped how I understand vulnerability in leadership.

In her foundational work Dare to Lead, Brown defines vulnerability as "uncertainty, risk, and emotional exposure"—the emotion we experience during times of risk-taking and when we feel exposed.

Here's what might surprise you: Brown's research revealed that "you can't get to courage without rumbling with vulnerability."

After interviewing leaders from various fields—including military Special Forces and NFL athletes—she found that courage and vulnerability are inseparable.

There is no courage without vulnerability.

This challenges everything many of us learned. Most of us were raised to believe vulnerability is weakness.

But Brown's longitudinal study on brave leadership proved otherwise.

What she found is that, when leaders are willing to be vulnerable, they don't become weak—they become capable of the kind of courageous action that transforms organizations.

I’m finishing up now her latest book, Strong Ground, in which Brown offers a central metaphor—finding your strong ground—that comes from her experience learning to establish physical stability during a time of intense rehabilitation for a sports injury

She describes grounded confidence as an athletic stance: rooted enough to provide stability, but flexible enough to move with purpose when change demands it.

This grounded confidence emerges from doing the deep internal work—self-awareness, values clarification, genuine connection with others.

The concept of "grounded confidence" is at the heart of strategic vulnerability.

What makes Strong Ground particularly relevant for school leaders is Brown's emphasis on paradoxical thinking.

Leadership today requires holding two seemingly opposing truths at once: being confident while staying humble, moving with urgency while remaining thoughtful, standing firm in your values while remaining open to growth.

In her conversation with organizational psychologist Adam Grant about paradox, Brown explains that when faced with seemingly opposing ideas, our natural cognitive wiring pushes us toward certainty and clarity. We want to resolve the tension quickly—to pick a side and move on.

But effective leadership requires something different: recognizing that you're in a paradox and holding the tension until something better than either option emerges.

This is where strategic vulnerability becomes essential.

When school leaders can name the paradoxes they're navigating—"I need to be decisive AND I need to listen more," "We need stability AND we need to innovate," "I must hold people accountable AND show compassion"—they create space for their teams to do the same.

The vulnerability isn't in admitting confusion; it's in acknowledging the genuine complexity of leadership and staying present with the discomfort until clarity emerges.

Strong ground doesn't mean having all the answers.

It means being stable enough to hold the questions.

Brown identifies "the discipline, humility, and confidence to unlearn and relearn" as one of the toughest—and most essential—skill sets for modern leaders.

This is strategic vulnerability in action: Being secure enough in who you are to acknowledge what you don't know and adapt when necessary.

Take a listen to Brown and Grant discussing the paradox of grounded leadership for yourself here:

Naming the hard truth. When you're facing a difficult decision—budget cuts that will affect real people, a policy change that will upset parents, a personnel issue—don't hide behind bureaucratic language. Be direct: "This is going to be difficult. Here's why we need to do it anyway."

Owning your mistakes honestly. When you make a call that doesn't work out, don't spin it or move on quickly. Stand in front of your staff and say: "I made this choice. It wasn't the right one. Here's what I've learned, and here's what I'm doing to make it right." This shows that leadership means taking responsibility for consequences.

Letting people see your growth edges. Share the decisions that challenge you. The conversations that require courage. The moments when you weren't sure of the path forward. "I've been wrestling with this for weeks" or "This decision hasn't been easy." When leaders acknowledge challenges, they give permission for others to do the same.

Saying the "No" that protects the better "Yes." Sometimes leadership means making choices that disappoint people in the short term to protect what matters most. Saying no to opportunities that would look good but would compromise your core values. Making the choice that's harder now to prevent deeper problems later.

Standing by your convictions. There will be times when you're the lone voice. When the easier path is right there, and you choose the harder one anyway. Strategic vulnerability means having the courage to stand by what you believe is right.

Trust deepens. When your staff sees that you're genuinely invested in this work, that you're making difficult choices for the right reasons—they follow you into hard places. Not because you have all the answers, but because they know you're committed alongside them.

Your culture shifts from performance to purpose. When vulnerability isn't just tolerated but modeled from the top, people stop pretending. The masks come off. The real work begins. People start bringing their full selves to the work.

Hard conversations become meaningful. When you've normalized honesty about challenges, those difficult conversations about performance, vision alignment, or staffing decisions stop feeling like administrative tasks and start feeling like what they are—acts of care that require courage.

As Brené Brown reminds us: "Courage is contagious."

When you show up authentically, you give permission for everyone else to do the same.

Strategic vulnerability is NOT:

It IS:

The difference matters.

Sit with these for a minute:

What has your leadership required of you? If the answer is "not much," you might be managing rather than leading. What are you willing to commit to for the vision you carry?

Where are you hiding behind the mask? What challenges could you be more honest about? What authentic moments could you share that might give others permission to be real?

Are you willing to stand alone when necessary? To make the unpopular choice? To say the "No" that protects the better "Yes," even when it costs you politically or professionally?

What are you deeply committed to? What would you advocate strongly for? If you don't know, it's time to figure it out.

Leadership that doesn't involve some struggle, challenge, and difficult choices might be many things—but it's probably not transformational leadership.

Your school community doesn't just need a manager who keeps the ship afloat.

They need a leader who's genuinely invested in a vision worth committing to.

That's the kind of leadership that changes lives.

That's the kind of leadership that creates cultures where everyone can flourish.

That’s a vision of leadership that arises out of wholehearted and authentic vulnerability

Here's to leading with our whole hearts—authentically and courageously,

Scott

Ready to take the next step forward?

Everything I'm sharing in this newsletter series is drawn out in much more robust detail in my resource: The Flourishing School Leader's Field Guide

This field guide explores how you can lead with hope, celebration, gratitude, hospitality, and vision—and yes, with courage and vulnerability too.

Whether you're feeling inspired and want to sustain your momentum—or exhausted and in need of renewal—this field guide is your companion for leading with courage, clarity, and care.