What does leadership look like? What does the path to leadership look like? People often talk about leaders and leadership as if they are fixed, discrete concepts. But definitions vary, and what makes someone a leader has everything to do with how they see themselves.In independent schools, there’s something of a standard trajectory to school leadership—teacher, division leader, division head, administrator, head of school. But what happens when you don’t see yourself on that exact path? When you don’t see people who look like you in positions to which you aspire, do you forge your own path? That’s what we found ourselves wondering as we approached veteran status in roles we were outgrowing.
Before we met at a conference in 2019, we were serving as college counselors at independent schools on opposite ends of the country. Although we were at very different schools, we were each wanting to break out of our counselor roles, but we didn’t know how to get started or where to go; the next step seemed elusive and unclear. We were starting to see ourselves differently and knew we needed to make a change.
As we enter a new school year, we reflect on our stories, how we found each other, and how we developed a way to propel each other forward as we navigated our careers—together.
Before We Met
Joy Prince: I began my career teaching upper school French and serving as an adviser at a coed independent day school. A move out of state gave me the opportunity to reinvent myself, and I spent the next nine years in college admission and college counseling. I tested the waters of leadership as a grade-level dean at a pre-K through 12 school. After five years as director of college counseling, including two as a grade-level dean, I paused my career to start my family.In 2015, as my children reached elementary-school age, I returned to the workforce in college counseling. But an invitation from an African American female head of school to attend a local conference for people of color in independent schools changed my path. The conference sparked my interest in further pursuing leadership. The sessions revolved around managing versus leading, the importance of social capital, effective governance, and all things related to executive leadership. Suddenly, leadership didn’t feel unattainable. Seeing heads of color directly impacted how I saw myself growing and leading in independent schools in a way I hadn’t before.
This was my lightbulb moment; I realized the need to leverage my skills and learn new ones to grow beyond my role. Soon an opportunity arose at a new school, and although it was another college counseling role, in the interview I was open with the head and assistant head of school about wanting to move beyond the college counseling role. We discussed professional development opportunities to help me determine a direction and a path. The head recommended that I attend the Women’s Leadership Seminar, a three-day conference through The Head’s Network designed to give women a glimpse of what leadership looks like in independent schools.
Dot Kowal: After a career in the music and film industries in Los Angeles, I entered the independent school world in 2010. A decade later, I found myself a seasoned administrator with myriad counseling roles under my belt. I had just entered my third independent school and, in a meeting with my head of school, the conversation organically moved toward career goals and advancement. For the first time, I felt like I had a mentor in my head of school. Even though it felt risky, I told her that I didn’t see myself as director of college counseling for too much longer and felt ready to move on. I wasn’t sure that I could be seen in another role, but she was. She suggested I attend the Women’s Leadership Seminar.
Knowing that my head of school saw leadership potential in me that exceeded my college counseling expertise was a huge turning point, but my battle with imposter syndrome wasn’t completely over. When packing for the trip, I remember thinking that the way I presented myself would be supremely important as I entered a new group of professionals, all of whom I assumed would be much better versed in independent school culture via their own pedigrees, experiences, networks, and so on. As it turns out, I would meet another strong woman who would help me convince myself that school leadership was in the cards.
Keeping It Real
Kowal: When I met Joy, we talked about our aspirations beyond college counseling and how we only knew of a handful of women who had made a jump. I considered people in this role to be specialists, not generalists. I had expert-level skills and knowledge in college counseling, but I hadn’t had many leadership opportunities outside of that realm. Joy didn’t seem fazed by this issue—in fact, it was quite the opposite. While listening to the way she expressed her goal of using her college counseling directorship as a step toward a more senior administrative role, I heard a voice in my head that said that I needed to open up to seeing myself differently. Rather than perseverating on the question of “if” I could make a leap, I started investigating the “how.”In our relationship, we’ve heard and shared with each other authentic and honest advice. Sometimes it’s hard to hear, but it’s an incredibly important part of our leadership journey. These open discussions have become the way that Joy and I have related to each other on our path to leadership. For example, we’ve talked about whether heads need a terminal degree as a qualification to pursue headship. We once heard from a former head, who identifies as white, that she didn’t think it was necessary. Then a Black head of school countered that she believes there’s a different bar for entry into school leadership at most institutions if you are a person of color, in particular, a woman of color.
We have often discussed how, as women of color, it’s up to us to create our own pipelines because there just aren’t that many of us in independent schools. Questioning the status quo and the assumptions we make at our respective institutions has been key to examining how we want to function in our schools in the present as well as the future. Having each other as thought partners to interrogate our beliefs about ourselves and our professions illuminates areas of thinking that are potentially flawed or incomplete. The discourse that Joy and I have maintained has pushed us both to question, as well as to become more solid in, our beliefs and philosophies around our work, an important exercise as we began to pursue new opportunities.
Prince: At the conference, I met deans of students, diversity practitioners, academic deans, but very few college counselors. But as I perused the faculty résumés, I recognized myself in a few of them—French majors, grade-level deans, and teachers. Some were career independent school leaders who rose through the ranks or corporate leaders who transferred their skills. I realized that each of these highly capable and successful women didn’t start out having knowledge about every aspect of school leadership.
One head, speaking about managing school finances, explained that we don’t have to be the expert on every front, but we must be willing to learn. She implored us not to be afraid of what we don’t know. However, I did wonder if my path to leadership as a woman of color would be circuitous or straightforward. Dot and I realized that we were on nontraditional paths and needed to be intentional and deliberate about our work in order to advance. We’d soon learn that what happens after attending a professional development conference might be more important than the conference itself.
Building Each Other Up
Kowal: Joy and I committed to staying in touch and connected over the phone a few times before the end of the 2018–2019 school year. In our conversations, we focused on our career paths, our current roles (we both had more than one, including leading diversity, equity, and inclusion [DEI] initiatives), and how we wanted to develop. We spent equal time reviewing individual and professional goals and made lists of things we wanted to accomplish separately and together. We brainstormed ways we could join forces, including submitting proposals for workshops, writing articles, and finding ways to connect each other to people we knew, helping to expand each other’s networks. It would be another year of communicating back and forth before we would lead our first workshop together.First, in January 2021, we worked on a workshop for Carney Sandoe’s FORUM/Diversity called “College Counselors as DEI Change Agents.” This combined our college counseling expertise and our DEI work at our institutions. That fall, I was in the process of applying for the full-time DEI director position at my current school; I had been in the half-time interim role since the start of the year. I had never been through such a transparent internal application process, which involved interviews with current students and colleagues. Prepping would be different than anything I had experienced before. Joy was a constant source of support both emotionally and professionally. From reviewing interview talking points to helping me feel confident in just being me, she reminded me that I was already an important leader and that my identity and experiences would bring strength to the role. When I was offered the position, she was the first person to send me a gift—two important books: Diversity in the Workplace: Eye-Opening Interviews to Jumpstart Conversations about Identity, Privilege, and Bias by Bärí A. Williams and Blindspot: Hidden Biases of Good People by Mahzarin Banaji and Anthony Greenwald.
Prince: After our phone conversations, we always shared a follow-up email with what we discussed and an action plan. I appreciated that we assigned each other tasks and enjoyed collaborating. This was most evident when our proposal to present at Carney Sandoe’s FORUM/Diversity was accepted. With this co-presenter experience under our belts, we submitted a proposal for the fall 2021 conference of the National Association for College Admission Counseling, which has been conditionally accepted at the time of writing this article. Buoyed by the flow of our work together, within a few months, I began a search for a new role, eventually choosing to pursue upper school head opportunities. Dot, who was on the tail end of interviewing for the director of DEI at her current school, provided consistent support. Through calls, emails, and texts, we kept each other apprised of our processes and encouraged each other to express our authentic selves in our interviews, reminding each other that we were ready to take the next right step.
Despite additional roles and balancing work and parenting responsibilities during the pandemic, our determination paid off, and we both accepted new positions in February 2021. Not long after, I approached Dot about submitting another session proposal, this time for the NAIS People of Color Conference. Our natural, symbiotic relationship allowed us to work effectively and swiftly to flesh out ideas for the proposal, titled “Women on the Way Up,” which would be an affinity space for women of color who wish to pursue leadership roles in schools. I celebrated with Dot after she published on Medium and again after she was invited to be a keynote speaker for the 2021 Carney Sandoe Women’s (Re)Institute. I offered my support to help her prepare for her keynote address. All the while, we amplified and congratulated each other on social media.
Kowal: After two and a half years of immense effort on both sides— submitting proposals together, co-writing, and seeing each other through job application processes—Joy and I have developed a natural rhythm. We made time even when we were extremely busy. We listened, texted, called, and Zoomed. Joy was in the process of packing up her entire house for a move out of state when she helped me practice a keynote speech. We always show up for each other. In independent schools, it’s easy to feel like I don’t belong, whether that is because of my race, class, or gender. When in doubt about “my place,” I know Joy will reflect back to me all the ways in which I can lead despite this, and it will be when I need it most.
Prince: We will continue to support one another and celebrate each other’s successes: To partner and genuinely engage with a colleague requires an extremely high level of commitment, especially when you’re in different time zones. It was apparent to both of us that we needed a thought partner who was outside of our day-to-day work environment so we could offer perspective as well as reality checks. We’ve made a genuine effort to keep each other moving forward, because we are on a journey to build each other up, regardless of the outcome for ourselves. Perhaps the path we have taken and our deep connection will be an inspiration to others. Aspiring leaders can use our framework to form bonds that will take them steps beyond what the standard professional development conference can provide. It’s not just about rising up in leadership; it’s about rising up in leadership together.
Future Forward
Women of color more often than not find themselves in the minority—not just in their communities but in their workplaces, administrative teams, and faculties—when they show up as leaders. As women of color who have ascended to leadership positions from nontraditional leadership-path roles in independent schools, we believe that the key to ensuring that more women of color become heads of school and enter other leadership roles is connecting and reflecting on our experiences together.Our connection has ultimately served both of us in profound ways, and quickly. We have been intentional about forging this path because we have to be. Our genuine connection from the beginning was organically rooted in a desire to support one another, to inspire each other to make positive change at our schools, and to encourage each other to pursue our short- and long-term goals.