Waking up to our Own Bias: A School Leader’s Journey

An educator shares her journey in noticing bias, learning, and realigning with core values, to make her school a place of true belonging.

August 17, 2022

By Cheryl Maayan





Cheryl Maayan (she/her) is the Senior Program and Outreach Consultant for DSLTI, the Day School Leadership Training Institute. She recently completed fourteen years as head of Saul Mirowitz Jewish Community School in St. Louis.


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The school I helped build and grow had a culture of kindness, of respect for pluralism and exuded a love for every child — with all their quirks and challenges. So naturally, every child felt safe, welcome, and at home. 

Except they didn’t. 

Under the surface there were students who were feeling marginalized, and did NOT feel at home. They were LGBTQ+, and their needs were as yet unmet. I hope that other Jewish day school leaders — and anyone who cares about young people — can learn from our school’s experience.

A few years ago, one of our second graders transitioned, sharing a new name and pronouns that affirmed a long-felt sense of gender identity. The faculty and administration felt proud that we’d made a safe environment for this child, and were eager to show how we would ensure that this child could participate fully in all aspects of school life. 

However, in one area, I found I’d never really faced my own internalized bias: bathrooms. 

I was initially relieved that we had single-stall, “all gender” bathrooms in the office that the child could use. I assumed that these were the right bathrooms for the child. I was surprised, then, when the child’s parents reached out. They felt that asking their child to use the office bathroom rather than the multi-stall kids’ bathroom was sending the message that we did not “really” affirm their child’s gender. This policy singled out their child. 

As a school leader, it was my job to respond with openness. I quickly realized that I didn’t know enough about the issue to effectively articulate a position, or lead a discussion about it. 

When I used to teach, I always said, “The smartest people know where to look.” As a head of school, I’ve learned to surround myself with specialists – in finance, board work, even math education – every area where I’m expected to lead. I was grateful that the child’s parents helped me out with research and best practices about transgender students’ access to bathrooms. And in this case, I also needed to learn from transgender people and experts in LGBTQ+ children. 

I reached out to my own family members who are gender-expansive. I reached out to friends and colleagues in my circle with more experience. And I reached out to Keshet and was immediately met with care, resources, affirmation of my curiosity and uncertainty, and insight on how my decisions would impact LGBTQ+ children in my school. 

I found that my assumptions had been wrong. Without any awareness, I had been contributing to the feeling these children had of being marginalized. In order to change my perspective, and lead the school through change, I needed to be vulnerable and admit where I had been insensitive and uninformed.

The leadership team and the executive board started the project of setting things right by learning together. Through learning about transgender and nonbinary peoples’ experiences of exclusion and isolation, we came to understand the immense positive impact of affirming each child’s identity. I personally came to understand that while restroom access is far from the only area in which affirmation needs to happen, it represents a basic physical need that simply has to be met. Honestly, the moment that I really took in this truth was when I was at a theater with non-binary family members who were experiencing stress about which bathroom to use. 

I learned that when we place qualifications or limitations on “how far” affirmation can go — in this case, by singling out a trans child and preventing them from using the normal bathrooms used by other kids — we can cause real harm. 

Once our school leadership had internalized the real stakes of our decisions, we saw that the bathroom policy was a big opportunity to realize our core values of doing what is best for children and loving each child exactly for who they are. Our goal was to develop a bathroom policy that was clear for everyone, especially so that parents could know what to expect. While we knew that our encounter with this student was the catalyst for our learning, we wanted to create a policy that would also serve the many transgender and gender-expansive people we know are in our communities. 

Ultimately, we decided that all students should use the bathroom that felt most appropriate for them — whether that was multi-stall gendered bathrooms or single-stall all-gender restrooms in the office. We would not require any student to use the office restroom. We clarified that if any cisgender students, parents, or community members felt uncomfortable using multi-stall restrooms alongside trans and nonbinary people, those who felt discomfort were welcome to use the office restrooms. This policy ensures that everyone in our community can use restrooms in our building — a fairly basic component of belonging in our community!

The next step was to roll out our new policy to the whole community. While the board and leaders had spent significant time learning more, clarifying our values, and writing a new policy, the rest of the community had not gone on this journey. Because so many cisgender people are simply unfamiliar with trans folks, we prioritized educating parents to share what we had learned and why our values compelled us to create the policy that we did. We hosted a panel discussion, including a board member who is a transgender rabbi and a local Jewish pediatrician who is an outspoken parent of a transgender child and advocate for children’s needs. 

The initial reaction was mixed. Many families cheered joyfully and shared that this policy and the process behind it built their respect for the school. But some parents initially reacted with anxiety or even anger. It was really sad when a few parents were so committed to their biases that they led their children to be disrespectful to the child who was the first to transition at our school. 

Our work to educate our community was especially important in the face of the ignorance, misinformation, and, frankly, fear-mongering about transgender people that some politicians and right-wing extremists spread through our media and political environment today. I felt compassion for parents who carried the same misconceptions that I initially had. I also found it very upsetting to have to be a listening ear to people who disparage children. It took all of my mindfulness skills to maintain composure and speak respectfully in a way that would help people move forward. I felt shaken after at least one conversation, and lost my share of sleep. 

For a while, it felt like my whole job was to manage this policy change. I had learned from other periods of existential change in our school that many people naturally resist change. But I also knew that sticking with it through many, many personal conversations would help. I also realized that this change wasn’t unmanageable or even unprecedented: ten years ago, our school experienced a merger that unsettled our community for several years. In a busy school year, when my plate was already very full, it felt like the bathroom process was sidetracking the routine. But this change was an opportunity to become a better school for all children. It was exactly the kind of work a school leader should be fully engaged in.

Belonging for transgender and nonbinary students goes beyond the question of restrooms (and related logistics about bodies and privacy, like during overnight school trips). For example, we have updated our reproductive and sexual health education to ensure that all students have clear information about how bodies work, free of harmful assumptions that biology equals gender. At our school, pediatricians from the community help teach students about their bodies, puberty, and sexual/reproductive biology. During these lessons, the doctors now use language that makes clear when they are talking about anatomy and when they are talking about gender. So, instead of saying “girls typically begin menstruating…” they say, “people with uteruses typically begin menstruating…”. If this kind of language feels awkward or new, for students or parents, that is okay! What a wonderful opportunity for lifelong learning and for cisgender people to shed our assumptions. 

Beyond the bathroom policy, we joined Keshet’s cohort-based Leadership Project in order to audit the school, update policies and procedures, and provide training for the staff. Now, when we interview potential new staff members, we articulate our values of LGBTQ+ belonging and ask directly how the candidate can contribute to this school culture. 

I’m proud that our school has become a more comfortable place for LGBTQ+ students. Another student transitioned a year later, and several other students and alumni have come out as lesbian, gay, bisexual, and/or nonbinary. We hope that all our LGBTQ+ students, families, and staff — and everyone in our whole community, all our diverse and unique selves — feel respected and at home. And I hope that other school leaders can learn from our experience. Here are a few lessons that helped move our school towards LGBTQ+ equality and belonging:

  1. Wake up to your biases. You can be gentle with yourself while being rigorous in examining and letting go of your assumptions. Mine were at least partially rooted in my cisgender identity, and many cisgender people today are unfamiliar with trans people.
  2. Surround yourself with experts, both those with simple lived experience and those with policy and process expertise. I needed to talk through our school’s issues with trusted trans friends as well as experienced equity and inclusion coaches like those at Keshet.
  3. Learn and listen while holding on to your core values. For me, this meant remembering that our school is a place where every child is loved. That commitment kept me centered through frustrating conversations and helped me get back on track when I worried that what we were doing was too hard for our community.
  4. People resist change, but they also want to do the right thing and they’re totally capable of it. Good leaders help individuals and communities get unstuck and reorient to what’s possible.
  5. You don’t have to complete the work, but you’ve got to get started! It’s fine to start with what your students need and go from there, whether that’s bathroom policy, sex ed class, or something else. When you see what a difference your work is making, you’ll know it was worth it and be motivated to keep going.

As the school year starts, many school leaders feel like we’re facing impossible challenges. LGBQ and especially trans, nonbinary, and gender-expansive kids are at the center of raging debates in our whole society. But they didn’t ask to be. As adults, teachers, parents, educators, Jewish leaders, and community members, we want our kids to be just who and how they are, and to grow up healthy and safe. I hope that this year brings each of us many opportunities to see our students and children blossom — and many opportunities for kind and courageous leadership.