In a recent episode of The Table, I had the privilege of sitting down with Nicole McDermott, ACC, an educator, former head of school, ICF-certified coach, and Dare to Lead facilitator trained directly by Brené Brown. Our conversation explored what it truly means to lead with vulnerability, build trust in school communities, and show up with courage during uncertain times. Nicole’s insights offer a roadmap for school leaders navigating the complexities of modern educational leadership.
The Foundation: Connection and Making a Difference
Nicole’s career spans over 20 years in education, including 18 years as a head of school, starting at just 26 years old. When I asked about the through line across all her roles, she identified two core elements: making a difference and connection.
“Connection is the energy that’s created when people feel seen, heard, and valued,” Nicole explained, referencing Brené Brown’s definition. This wasn’t just professional philosophy for her. It was something she knew she wanted to pursue since second grade, when she decided to become a teacher. That vocational calling still shapes everything she does today, even three years after leaving her position as head of school.
What struck me most was Nicole’s emphasis that everything she does flows from being a teacher first. Whether she’s coaching executives, facilitating Dare to Lead workshops, or consulting with schools through Educational Directions on leadership searches and transitions, that teacher identity remains central.
Trust: The Currency of School Leadership
Throughout our conversation, trust emerged as perhaps the most critical element of effective school leadership. Nicole grounds her work in four principles: mutual trust, warmth, integrity, and vulnerability. She noted that trust has been important to her since childhood in ways her peers didn’t always understand.
Drawing on Charles Feldman’s work, Nicole described trust as “choosing to risk that something valuable to me is safe with another person.” She’s expanded her understanding of integrity beyond simply doing the right thing to embrace Brené Brown’s definition: “choosing courage over comfort.”
In her coaching practice with Quality Matters, Nicole sees trust issues underlying most leadership challenges, even when leaders don’t explicitly name them. “If we can understand how our actions, big and little, are our ways to build trust, I think it can go a long way,” she said.
The challenge? School leaders operate at breakneck speed. John Gottman’s research shows that trust is built in small moments, but those moments of intentionality often get lost in the daily chaos of running a school. Nicole believes many leadership challenges would diminish if schools concentrated more deliberately on these trust-building moments.
Vulnerability Isn’t Weakness: It’s the Foundation
For many school leaders, vulnerability feels like a four-letter word. Nicole acknowledges that this resistance is natural. We want to avoid anything scary, hard, or uncomfortable. But here’s the paradox she illuminated: we can’t actually avoid vulnerability. It’s happening all around us constantly.
“The first step is just to acknowledge: this is hard,” Nicole said. “This might be a tense meeting, or I feel tension. Whatever it is, acknowledge it. Have that self-awareness to name it.”
She offered practical examples of intentional vulnerability in action. Before a difficult meeting with a parent or teacher, a leader might say: “I think we might be in for a hard conversation today. What’s not hard at all for me is to say I really care about you and I care about what we’re talking about. Let’s ground ourselves there.”
Any moment of repair requires vulnerability. When we snap at a colleague or don’t show up as our best self with a student, going back to make it right takes courage. These opportunities arise constantly in schools.
Nicole shared a lighter example from facilitating a Dare to Lead workshop. Standing in front of the group, she noticed one curl hanging lower than the others. Rather than pretending everything was perfect, she called it out with humor: “I just want to embrace a moment of vulnerability and share with you that no day with curly hair is the same. You might note this one curl that’s hanging down.” It got a laugh and set the stage for authentic learning together.
However, Nicole was careful to acknowledge that vulnerability isn’t equally accessible to everyone. Systems of oppression can make it unsafe for some individuals to be vulnerable. “My hope is that at the very least in our school communities, everybody, no matter what their identity, no matter where they’re from, can show up and really be seen,” she said. For those who can show up with vulnerability more easily, that creates an opportunity to show up with courage for others who can’t.
Leading Through COVID: Lessons in Uncertainty
Nicole was a head of school during the pandemic, an experience she believes warrants support groups for everyone who led through that time. The uncertainty forced leaders to embrace vulnerability whether they wanted to or not.
“There are more questions than answers right now,” Nicole would write in her community emails. “At some point, that will flip. Thank you for your trust, and we’re going to have grace with each other in the meantime.”
She even changed her email signature from “Onward!” to “Onward,” because the exclamation point felt like too much given the weight everyone was carrying.
The pandemic reinforced two crucial lessons Nicole now brings to her coaching work: giving yourself grace and concentrating on what you can control. “COVID was an uncertain time, but in the present day, we have uncertain times too,” she noted. “In those periods of uncertainty, how can we show up and concentrate on what we can control?”
She reflected on being in her 15th year as a head when COVID hit and thinking, “I have no idea what to do.” The answer was to lean into all the things that had made her a good leader. Leaders don’t need to be experts on everything. Sometimes leadership means admitting you don’t know and working through challenges together.
The Shame vs. Guilt Distinction That Changes Everything
One of Brené Brown’s most powerful research findings distinguishes shame from guilt. Shame says, “I am bad.” Guilt says, “I did something bad.” This distinction has become central to Nicole’s work.
“If they say something that is shaming language, I will redirect that,” Nicole told me. She’s made it a personal mission to help people reframe their self-talk, whether with four-year-olds in her office as a head or with adult leaders she coaches.
With young students, this looked like saying: “You are not a bad kid. You made a bad choice.” Did every four-year-old fully grasp the distinction? Maybe not. But it mattered that adults in the community were intentionally living out that value.
The narrative we play in our heads profoundly impacts our well-being and effectiveness. Nicole describes herself as “a recovering perfectionist” who understands firsthand how people with perfectionistic tendencies are hard on themselves. Their self-talk isn’t positive; it’s shame-filled. Changing that internal dialogue is transformative work.
Building Trust in Leadership Transitions
Through her work with Educational Directions, Nicole guides schools through leadership searches and transitions. She’s observed patterns in what schools look for and, importantly, where they sometimes miss the mark.
Nicole drew a parallel to prospective families who tour schools focused solely on academics. Of course, academics matter. But there’s so much more: character building, leadership opportunities, confidence development, peer relationships, and community. Similarly, schools in leadership searches often focus exclusively on finding the next right leader while overlooking crucial surrounding dynamics.
“Searches don’t happen in isolation,” Nicole emphasized. “There’s uncertainty, there’s fear, there’s anxiety, there’s grief—often from different stakeholders for different reasons. It doesn’t make sense to gloss over that or not give it the attention it deserves.”
This holistic approach to searches sets up new leaders for success. When a school has already addressed fears and feelings in the community, the incoming leader has a better foundation.
For new leaders themselves, Nicole’s advice centers on authenticity and curiosity. Borrowing from the book Unreasonable Hospitality, she counsels: “Do not cannonball into the pool when you are new. Ease in.”
New leaders should ask more questions than they tell or implement ideas. “At some point that will flip,” Nicole acknowledged. “But at the beginning, it needs to be more questions than certainty.”
We often don’t allow new leaders time to pause and breathe. Everyone wants them to do things, fix things, change things. But leadership transitions require collective patience. “Everyone just needs a collective deep breath,” I reflected during our conversation. “This person is here, everyone’s okay now. Let’s see how we want to move forward.”
Nicole agreed enthusiastically, adding that setting boundaries and saying no—even as a new leader—can be done with warmth and connection. New leaders need permission to pace themselves, and “even if it’s just coming from us on this podcast, we give you permission.”
Daily Practices That Ground Leaders
Nicole’s leadership is anchored by daily meditation and gratitude practices. These aren’t just professional habits; they’re central to who she is as a person. And as she notes, “who we are is how we lead.”
More than a decade ago, when Nicole was head of school, she brought mindfulness practice into her school “before it was trendy to do that.” The concept was simple but powerful: creating space between reaction and response. “If we can respond, we’re going to come from a stronger place than if we’re going to react.”
Now, whenever Nicole facilitates a workshop, she starts with a “pause plus five”—sitting in your mindful body, feet on the ground, breathing in and out while tracing your hand. In one-on-one coaching, she explores what Kristin Neff’s research defines as mindfulness: naming our feelings and feeling our feelings without over-identifying with them or getting wrapped up in charged reactivity.
Nicole’s gratitude practice, inspired by Oprah, has been consistent for over 20 years. She keeps a daily gratitude journal, and she credits this practice with changing her life. “I started to notice that I could get to something I was grateful for quicker, even when something was really hard,” she said. “You almost go through the world looking for things to be grateful for.”
In a revealing moment, Nicole shared that she purged all her gratitude journals over the summer. She’d never looked back at them, and she realized the practice was about being present, not creating an archive. She’s even stopped caring what her handwriting looks like. “I’m writing this down because it’s important for me to process it and note it, and I’m probably never going to look at it again. And this journal is going to get thrown away when it’s done, and that’s okay.”
For someone who describes herself as “a keeper of stuff,” that’s freedom.
What’s Next: Choosing Courage
When I asked Nicole what’s next, she was characteristically thoughtful about the moment we’re in. “This is a hard moment in time,” she acknowledged. “The opportunities to show up as a courageous leader, as a daring leader, are very present. There’s a lot of opportunity.”
The challenge is pacing ourselves to take care of ourselves while also showing up with courage. And for those who can help people who need our help right now, that’s critically important work.
In schools specifically, there’s no shortage of moments where courage is needed: one-on-one conversations, classroom interactions, board meetings, presentations with families. “What’s next for all of us is hopefully continuing to choose courage and continuing to show up as our whole selves to the extent that we can, where it’s safe to do that,” Nicole said.
The Bottom Line
My conversation with Nicole reinforced something I’ve believed throughout my career in education: the most effective school leaders aren’t those who project invulnerability or have all the answers. They’re the ones who show up authentically, build trust through small daily actions, acknowledge uncertainty, and create space for others to be seen, heard, and valued.
Vulnerability isn’t weakness in leadership. It’s the foundation for everything else: trust, growth, transparency, risk-taking, accountability, and the warm, challenging environments where students and adults thrive.
Whether you’re a head of school, division director, teacher, or coach, Nicole’s insights offer practical wisdom for leading with greater intention and courage. Start small. Name what’s hard. Ask more questions. Build trust in moments. Give yourself grace. And remember that the narrative you tell yourself matters deeply.
If you’d like to learn more about Nicole’s work, you can find her at nicolemcdermott.net or on the Educational Directions website. She offers executive leadership coaching, Dare to Lead facilitation, Clifton Strengths coaching, EQI assessment, and grief education.
As Nicole said toward the end of our conversation, continuing to choose courage and show up as our whole selves is the work ahead. In this challenging moment for education, that work matters more than ever.
