HLP Voices Series #8 - Breaking the Mold: Siobhan O’Brien on Leading in a Male Dominated Leadership Culture

Early childhood education is one of the few sectors where women make up the majority of the workforce. Yet when it comes to leadership, a different picture often emerges. Globally, around 75% of educators in international schools are women, but only about 30% hold top leadership positions. In the United States, women represent more than 80% of the teaching workforce, yet just 30% of superintendents in the largest districts.

Leadership in education, especially in international settings, still carries gendered barriers, biases, and expectations. That is precisely why the journey of Siobhan O’Brien is so inspiring.

With nearly twenty years of experience across the United Kingdom and Thailand, Siobhan is now the Head Teacher at Raintree International School, one of the most respected early years institutions in Bangkok. She has served as Assistant Principal and Acting Vice Principal at Shrewsbury International School and has worked with educational charities in Uganda and Sierra Leone. Her leadership style is rooted in trust, curiosity, and a strong belief in the potential of every child and every educator.

In this conversation, Siobhan opens up about leading in a space where women are present but often not in charge, her passion for outdoor learning, and the advice she would give her younger self just starting out.

Let's dive in.

Pınar: Siobhan, you’ve worked across continents and cultures, and your passion for early years education really shines through. I’m curious, what first sparked that interest for you? And how has your connection to this work evolved over time?

Siobhan:My journey began with a deep curiosity about how children make sense of the world. I have always been fascinated by the way young minds explore freely, ask questions without hesitation, and express themselves with honesty and imagination. Coupled with a strong interest in brain development and knowing that the majority of brain growth happens within the first five years, my focus naturally turned to early childhood education.

The experiences children have in those foundational years shape the very architecture of their developing brains. It is powerful and humbling to recognize the impact we have as early years educators.

Working across cultures has deepened my appreciation for culturally responsive education. To me, it is not just about teaching. It is about listening, adapting, and creating environments where every child feels seen, safe, and valued.

Today, I see myself not only as an educator but also as an advocate. My passion continues to grow, fueled by the incredible children, families, and educators I have had the privilege to learn alongside.

Pınar: It’s clear that your sense of purpose has stayed strong through all these different contexts. From the United Kingdom to Thailand, you’ve seen a wide range of school systems. What would you say are the values that have consistently anchored your approach, no matter where you were?

Siobhan:Working in both countries has given me a rich perspective on how school systems differ. While the demographics and contexts have varied, the values that have remained constant for me are connection, respect, and curiosity.

Children thrive when they feel genuinely connected to their teachers, peers, and environment. They need to feel safe and supported by trusted adults who guide them with empathy.

Respect is essential. Respect for children as capable individuals, for families as partners, and for the cultural context we are in.

Curiosity keeps the work dynamic and joyful. Encouraging it in children, and modeling it ourselves, brings depth and joy to the learning process.

These values have helped me stay grounded in what truly matters, nurturing confident, compassionate, and creative learners.

Pınar: You mentioned connection, respect, and curiosity as your guiding principles. And yet, in many international schools, especially at the leadership level, we don’t always see those values reflected in decision-making. Given that Early Years education is so female-led in the classroom, how have you navigated stepping into leadership where women are often underrepresented at the top?

Siobhan:The gender imbalance in education leadership is still deeply rooted. Although women make up the vast majority of the workforce, they remain underrepresented in senior leadership roles. In the United Kingdom, women are twenty percent less likely than men to become headteachers. In Thailand, out of the top ten leading international schools, only one has a woman at the helm.

I did not pursue leadership for the title. I stepped into it to make a broader impact. I wanted to advocate for children, raise the status of Early Years, and create environments where educators feel supported and valued.

But stepping into leadership also revealed the gendered expectations that persist.

Assertiveness is perceived differently in women. Relational leadership is often dismissed as soft. And many women are overlooked because the leadership pipeline was not designed with them in mind.

In my own leadership journey, I have tried to model values driven leadership and to lift up other women who are ready to lead. I believe deeply in creating space for men in Early Years as well—not as a gesture of balance but because children benefit from a wide range of role models. Caring, empathy, and playfulness are human strengths, not gendered traits.

Ultimately, we need leadership that reflects the values of Early Years. That means rethinking who gets to lead and why.

Pınar: I’m wondering, from your perspective, what can schools do differently, both practically and culturally, to make leadership more accessible and sustainable for women?

Over 80% of women leaders in education report facing bias in their roles. Many say they feel pressure to monitor their behaviour and appearance due to heightened scrutiny.

Siobhan:First, schools need to name the imbalance and commit to addressing it. That begins by identifying and nurturing leadership potential in women early, offering mentoring, and creating clear pathways forward.

Many experienced and skilled women are never told they could lead. Or they do not see themselves in the existing leadership models, which often reward a narrow set of traits. We must expand our view of leadership to include collaboration, emotional intelligence, and relational strength.

Flexibility is also crucial. Many women are balancing leadership aspirations with caregiving responsibilities. Schools that offer flexible structures make it possible for more women to thrive.

Representation matters too. We need leadership teams that reflect a broad spectrum of experiences, including women, people of color, and others from underrepresented communities. It is not just about opening the door. It is about making everyone feel welcome in the room.

Pınar: And beyond systems, there’s the personal side of leadership too. You wear many hats: school leader, consultant, mother, runner. I know that kind of balance doesn’t just happen. How do you make space for all the parts of yourself while leading with intention?

Siobhan:It is an ongoing process of reflection and readjustment. Some days I feel like I am juggling more than I can carry.

Since becoming a parent, I have become more intentional with my time. My husband’s unwavering support has made it possible for me to pursue leadership and remain present as a parent.

Running and strength training are non negotiable for me. They are not just physical outlets, they are how I process, reset, and come back to myself.

I have learned that when I let go of that space, I become overwhelmed. And when that happens, I cannot show up the way I want to for my team or my family. Taking time for myself is not a luxury. It is essential.

Pınar: That sense of intention seems to carry into everything you do, including your international work. You’ve spent time in Uganda and Sierra Leone supporting educational projects. What drew you to those experiences, and how do they continue to influence the way you lead today?

Siobhan:I was drawn to both countries by the chance to engage with communities that face real challenges yet remain committed to education as a path forward.

In Uganda, I worked on the development of an education center and preschool. In Sierra Leone, I supported teacher training at a summer camp. In both places, I was inspired by the dedication and resilience of educators who created learning opportunities with minimal resources.

Children and staff often walked for miles to reach school. Their passion and perseverance were humbling.

These experiences taught me resourcefulness, humility, and the importance of community. They reminded me that the core principles of education—respect, connection, and belief in every child’s potential—are universal.

Pınar: You’ve worked with so many children and educators over the years. I imagine the impact goes both ways. What do you hope your team and your students carry forward from your leadership and the time they’ve spent with you?

Siobhan: Confidence. I hope they feel seen, heard, and capable of creating change.

For my team, I want them to know that leadership is not about knowing everything. It is about collaboration, resilience, and learning together. I want them to take risks, grow through mistakes, and lead in their own ways.

For my students, I hope they leave with a love of learning. I want them to know their voices matter, their creativity is welcome, and they can shape their own futures with courage and curiosity.

More than anything, I hope they remember that leadership is about service—helping others grow into their potential.

Pınar: I  always end with this one, it’s my favorite. If you could sit down with your younger self, just starting out as a teacher, what would you say to her now that you’ve seen the journey from this point?

Siobhan: Trust yourself. Challenge more. Early in my career, I followed systems and approaches I instinctively felt were not right for children. But I did not speak up because I did not believe I could.

Now, I encourage others to trust their instincts and speak when something does not feel right.

And I would remind her to care for herself too. This work is meaningful but demanding. You do not need to carry it all alone. Rest is not weakness. It is what allows you to keep going with heart.

Siobhan O’Brien reminds us that leadership is not defined by titles or traditions. It is defined by presence, purpose, and the courage to lead with values that center people, not systems. Her journey shows what it means to advocate from within, to build inclusive cultures in spaces where women are present but still underrepresented, and to lead with both strength and softness.

At Her Leadership Playbook, we believe stories like Siobhan’s deserve to be heard widely. They challenge old narratives and invite new ones: ones where educators lead boldly, where care is a leadership skill, and where every child and every teacher feels seen.

We are proud to feature Siobhan in our HLP Voices series and grateful for her commitment to equity, early education, and shaping a leadership culture that begins with trust.

If her story moved you, let her know. You can connect with her on LinkedIn here:Siobhan O’Brien on LinkedIn