The Puzzle: Blog

This is a piece from CS&A's winter focus on diversity, equity, and inclusion in schools. Read more from this series here.

For too long, it has long been understood that if you want to be a head of school you should avoid being a director of diversity first, or at the very least limit your time in that role. Although the trend in most schools today is to position the diversity, equity, and inclusion (DEI) role as a senior-level position answering directly to the Head of School, the prevailing narrative remains that there is a lack of transferable skills from the those employed in the role of Director of Diversity to those needed as Head of School — that the Director of Diversity’s toolbox, in other words, is equipped solely for advancing equity and inclusion work. Beyond the limited, unimaginative perspective that this school of thought suggests, it demonstrates the overarching misunderstanding of the strategic, complex, and emotionally demanding work of leading DEI efforts at independent schools.

Now in my second year of headship, I find myself reflecting on the concrete ways in which my previous role as a DEI professional prepared me to excel as a Head of School. I outline these leadership skills here in hope that placement firms, boards, and search committees will consider the many talented Directors of Diversity currently working in schools when they are looking for excellent Heads of School to lead independent schools into the complex heart of the 21st century.

Lonely at the Top?

We’re often told, “It’s lonely at the top.” While this is a cliché, it underscores a truth about leading schools, especially independent schools. As a Head of School, not only do I find myself making decisions based on ripple effects that are often three or four times removed from an actual situation, but I also cannot always share the full context of my decision-making with colleagues, parents, and students. At times, I am the only one who holds all the facts or truths about a situation as I act in the best interest of the school. As a result, I can be misunderstood, misperceived, and critically judged — and I can do nothing to correct those narratives. It is also true that, as Head of School, having visibly close friendships with peers can result in the false perception of preferential treatment and perceived inequities among colleagues. Therefore, I do not have a peer at school with whom I can easily vent. Conversely, most colleagues, and many parents and students, can be so cautious when interacting with me, using a protective filter that makes it nearly impossible for me to fully know them as individuals or share in their experiences. While all of these situations compound to create a sense of loneliness in the headship job, my point here is this: It does not compare to the loneliness associated with being a DEI practitioner.

The loneliness of the DEI work as a person of color in a predominantly white community is a matter of the soul. Every day, you’ll have your humanity questioned or denied by those who resist the work. In order to create buy-in in an effort to advance the work of an institution that was most likely not created for people who look like you, you’ll find yourself having to bite your tongue over and over. You live with dual reality of what you say to folks and what you wish you could say to folks. DEI work often reminds me of the W.E.B Du Bois’s quotation, “Two souls, two thoughts, two unreconciled strivings; two warring ideals in one dark body….” Between those two thoughts lies the existential threat to your being, but also the well being of students and the needed evolution of the school community. For people of color, the loneliness in leading DEI work is deeply taxing on the spirit and psyche. It can, and does, wear folks down.

We know that marginalized groups in independent schools have to code-switch on occasion, yet people of color who are DEI practitioners experience a never-ending marathon of code-switching, all in an effort, ironically, to make their schools more inclusive. Being a DEI practitioner can feel like being a kite in the sky without a string because what grounds you are often the same ideals and values that your peers find threatening. DEI work requires two souls, yet there is only space for one at a time to be present. Those who manage this complex world well, however, develop leadership skills that very few people have.

If you take a moment and look at the first five paragraphs in this piece, you will see a noticeable progressive change in tone and language. The ideas and words in the first three paragraphs are designed to be inviting — to contain non-threatening language. By contrast, the last two are more direct and unapologetic. You can think of these five paragraphs as emblematic of the first three years of being a Director of Diversity in an independent school. Year one and two are spent strategically creating buy-in and building relationships so that in year three one can do the hard work of actually dismantling systems of oppression in our schools. Mirroring the experiences of a DEI professional, I chose to start this essay in a way that invites the reader in, holding off on language that could create walls of defensiveness, as so often happens in our schools. But I do make the shift to be more direct because this is what all schools need in order to pry open the lid and look honestly at community practices that undermine mission and institutional growth.

The Right Skills to Lead

More than ever, our students and faculty need leaders who have an unwavering moral compass. The state of independent schools and of our nation requires leaders who can talk intelligently about racial literacy and justice, the spectrum of gender and sexuality, systems of power and privilege. Our schools are in dire need of leaders who have the courage to unpack their own privilege; leaders who understand the urgency around the dismantling of power structures that privilege select groups and oppress others. Time after time, our students, faculty, and parents look to school leaders to help them make sense of the world around them. With more students growing up amid ideologies that are cradled by algorithms and a deeply polarizing social-political system, there is an urgency to teach our students about empathy and ethics. Morality and social consciousness should be prerequisites for the Head of School job; if you have not demonstrated proven success in modeling and teaching cultural responsiveness and racial literacy, one should not be a Head of School today. This position, which holds extraordinary symbolic power, requires those at the helm to be responsible for the collective conscious of their school community, and it is through DEI work, particularly as a Director of Diversity that one gains the skills to lead schools in creating morally conscious students.

Overall, people who work as diversity practitioners in independent schools have a remarkable skill-set that translates well to being Heads of School. They are highly principled, centered, and morally driven professionals who have both deep knowledge of institutional structures and the process of change. They are able to work well with all constituents — both adults and students — and connect with every office and every teacher in the school. They have extensive experience working with admissions, marketing, college counseling, and advancement teams. They know a great deal about establishing an evolving multicultural curriculum. They know how to work with the faculty in developing individual and collective cultural competencies. They know how to team with Boards of Trustees in establishing DEI goals and creating a pathway to success. They know a ton about creating an inclusive culture and supporting the social-emotional development of all students.

Perhaps more important than all these skills, DEI practitioners have extensive experience doing pastoral work, which is also a critical part of the Head of School job. As a DEI practitioner, you are consistently pastoring to bring comfort to folks so you can build relationships that will ultimately lead to creating inclusive communities. As a Director of Diversity, I was fortunate to work at a school that gave my position authority, not just autonomy. I had to craft messages to our school community to help make sense of horrific local, national, and world events and to infuse a feeling of comfort and community during moments of division. A typical example is the pastoral work I did for our community after the 2017 white supremacist rally in Charlottesville, Virginia. All DEI practitioners are tasked with creating learning moments out of situations that others often deem unfathomable. This work also includes constantly prioritizing the intellectual and moral growth of a school community.

Different but Similar

All this DEI work parallels the work of a Head of School. As a Head, I’m constantly thinking about the intellectual and moral growth of my school. I’m also ready to address crises. In September 2018, for instance, when wide-spread gas explosions hit Lawrence, Massachusetts, my hometown and the location of Esperanza Academy where I serve as Head of School, I felt well-prepared to do the needed pastoral work for my community.

Much of the success I have had in fundraising as Head of School is also a direct result of my training as an equity and inclusion practitioner. To be a successful equity and inclusion practitioner, one has to become a master of tone, read body language, and account for fragility. If you’re a man of color, you have to learn to have the right tone so as not to be perceived as threatening. If you’re a woman of color, you have to be careful not to let your strong will and sharp mind be perceived as too abrasive and accusatory. If these labels get placed on you as a DEI practitioner, the pace of creating truly inclusive communities dramatically wanes. Therefore, your management of communication and relationships is essential to the success of the job. Much like DEI work, fundraising as a Head of School requires skill in active listening and the ability to lean into various cultural cues to keep people comfortable while they engage in a high-stakes conversation. This aspect of DEI work and fundraising as a Head reminds me of an F. Scott Fitzgerald saying, “The test of a first-rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function.”

To be effective stewards in creating a more inclusive community, DEI practitioners must be highly skilled relationship builders. As it turns out, I have found the relationship-building skills I developed as a DEI practitioner to be invaluable in my current role, especially for fundraising. In truth, it is immeasurably more challenging to have, say, a conversation about healthy masculinity with male colleagues who perpetuate toxic masculinity, or with white colleagues who are armed with a shield of white fragility, than to ask a donor for a seven figure gift. All the aspects of managing hard conversations in the DEI position help build and strengthen one’s emotional intelligence and are absolutely transferable to successful fundraising as Head of School. Emotional intelligence, in fact, is at the heart of fundraising conversations. Understanding what excites a donor, what triggers them, and meeting them where they are, are critical parts of a successful donor conversations. Furthermore, whether it is with a student, faculty member, donor, or board member, the ability to listen well is a crucial part of being a Head. Through my experience as a DEI practitioner, I have fine-tuned these active listening skills, which have been essential in my success as a Head of School, especially in my first year.

Schools that treat the DEI role with the proper understanding and respect of the role inadvertently create practitioners who will, in time, be poised for the Head of School job. Similar to the Head of School position, the DEI role touches every aspect of school life and culture and intersects with all constituents. I encourage placement firms, boards, and search committees to look to those who have held this role when considering potential candidates for Head of School. The gross underrepresentation of folks of color in the Head of School role (8% of all independent school heads) needs to be addressed. Given that more than 88% of the people of color who enter independent schools in administrative positions come in through DEI positions, it is clear that there is not a shortage of candidates. It is time to shift the paradigm.

Jadi Taveras is the Head of School at Esperanza Academy in Lawrence, MA.

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3 Comments

Kate Knopp 2/12/2020 at 8:26pm

Cultural competence, emotional intelligence and an ethic of care are as essential to leading a school as are the more traditional metrics boards typically seek: financial literacy, management experience, endurance and good cheer to work long hours. We need to think more creatively about pathways to headship if we are going to envision a future that invites our schools to be more equitable and inclusive. DEI work is good training for headship — Jadi Taveras has that exactly right. Why would we want a school leader who isn’t engaged in this work and learning all the time?

Chris 10/2/2022 at 5:34am

Thank you, Jadi,

Reading this piece gives me confidence that I could be a HoS one day.

Madeleine Maceda Heide 12/3/2023 at 10:16am

I agree that DEI leaders have additional expertise and experience to bring to the table when dealing with challenging situations, equipping them to become amazing heads of schools. Those often-but-not-always subtle skills involve keen emotional intelligence and resilience, astute cross-cultural competence, and the nuanced ability to hold two truths while working towards a third. Thank you Jadi Taveras for this beautiful thought piece that should be read by all school leaders and aspiring ones too!