By Andrea Kasper

[This is the third in a five-part series on “Big Questions on Our Jewish Minds,” featuring alumni of the Day School Leadership Training Institute (DSLTI), part of the Leadership Commons at the William Davidson Graduate School of Jewish Education of JTS. You can join our series’ authors in conversation at the “Big Jewish Questions on Our Minds” session during the Prizmah Jewish Day School Conference coming up in March in Atlanta, Georgia.]

I grew up in a house that taught me that there were no limits to what I could accomplish or become. My parents vocally championed their feminism. This was the 1980s and I heard loudly and clearly that I could “have” everything. I am also the product of two national cultures, American and Israeli, and they both taught me, explicitly, that women were capable, tough, and equal.

Today, in my 40’s, I push hard and espouse all of the above with my family, in my place of work and in my daily interactions. I do feel like I have it all, and thus it may seem easy for me to say that we have achieved equality. Yet, that statement lacks appreciation and nuance of the reality. During my five years of leadership as head of school at the Solomon Schechter Day School of Greater Hartford, I have shifted from believing there was no appreciable difference for women leaders to processing the often disgusting things that have been said to me. I theorize that perhaps the rude and patronizing tones I meet with are due to my being a female head of school. Furthermore, I realized these troubling interactions weren’t just happening between men and me; it was also happening between women and me. It didn’t take long for me to realize that I was pushing against a much larger and more powerful force. As the national conversation began to include ideas of systemic racism and sexism, my understanding of my experiences expanded as well. Everyone with whom I interact is functioning within a world of systemic sexism; there is no way to avoid it. The hardest lesson of all became clear: I wasn’t only pushing against an external tide of sexism, I was pushing against the systemic sexism that had been ingrained in me.

Along with all the wonderful messages I received growing up, I was also told to be less emotional. I vividly remember the report card in middle school that reported that I was emotional – as a negative descriptor. Additionally, often my word was not believed until it was verified by another person (usually male). I was also trained to speak and argue in a very particular way. I learned to make hard and cutthroat arguments that left others feeling unheard and belittled. I internalized that being tough, logical, and non-emotional were superior to what I was otherwise. In the midst of this all, the advertising and media world filled my mind with images of men towering over women in the workplace, cigarette ads claiming, “we have come a long way, baby,” and rape culture and sexist humor as the norm for TV and movies. I learned that vulnerability was a sign of weakness and that “girly” wasn’t a compliment. I was determined to never be either.

Today, on a regular basis, I tune in to my own fleeting thoughts or reactions. I recognize now that these thoughts are steeped in sexist ideas and ideology. I ask myself, am I looking for a male authoritative voice? Am I dismissing an idea or thought because it’s “emotional?” Is my own self-doubt rooted in masculine ideas about leadership and decision-making? If I am to be completely honest, and completely vulnerable, then I have to answer yes to all of these. I have to face the reality that, of course, I am not outside of the system and that I am just as much a product of systemic sexism as anyone.

I have found that becoming increasingly aware and sensitive to my own biases as well as those of others is essential as I continue to grow in my leadership role as a woman. I ask myself more regularly from whom do I accept guidance and how am I biased in those choices; I look more carefully around the board table for where I seek affirmation and why. I also look more critically at the makeup of the board to think beyond gender and to identify how gender intersects with board roles and equal representation. Specifically, for four years we have had male business owners and CEOs on the board of trustees. That type of leadership is looked to for financial and management expertise by other trustees and me. For me, this created a situation where I looked for the most affirmation from these men. It took until this year to have a female business owner and CEO as part of our board and I recognize my bias more than ever. Am I looking to her for management and financial support? My honest and, not proud answer is, not yet, and I am forced to ask myself why not.

I also need to reflect on my role in how I can better develop other female leaders within the school. Sometimes these conversations are explicit about helping someone have a direct conversation about compensation or developing vision and agency to make change and to bring that change to the school. I seek out leadership professional development opportunities for faculty and support them as they embark on their learning. More often, and likely more importantly, I am trying to understand all the implicit ways that I communicate and model; it’s not necessarily difficult to reflect, yet it is hard to uncover the assumptions under which I function.

That challenge is even more apparent for me when I think about what I am teaching and modeling about female leadership to my learners who are of all genders. In what ways am I personally, and we as a school, perpetuating systemic sexism and bias? What are all the behaviors in which we encourage and appreciate in boys and minimize in girls and vice-versa? Does my tone of voice differ according to gender assumptions, and if so, how? How does a primarily female staff impact our biases? There are so many questions and they are difficult to answer. My work, first, is to try and figure out what questions will help me unearth my assumptions and biases and then to hold an honest mirror up and to try and understand what I see.

We all face our own very harsh internal critic and each one of us must contend with that. What I am left wondering about is how and when my internal critic is sexist, and whether I can identify it as such, and then… what do I do with it? I am also left wondering why I haven’t (yet) engaged in these conversations with leaders of both genders. I know that when we come together to share our experiences and thinking, we all leave enriched, more aware, and more capable of engaging in the work of honest reflection. Do these thoughts and questions resonate with you? This isn’t a question solely for female leaders; to make meaningful change we need all leaders engaged. When we all take on this work, in 10 years, we might be able to declare with strength and confidence, “we truly have come a long way, baby!”

Andrea Kasper is the head of school at Solomon Schechter Day School of Greater Hartford and teaches a master’s level course on Jewish day school education at Hebrew College. Andrea is an alumna the Day School Leadership Training Institute, a program of the Leadership Commons at the William Davidson School of JTS.