Leadership Lessons: How Heads Must Address the Challenges DEI Practitioners Experience Today

Fall 2022

By James Greenwood

Leadership Fall 2022

This article appeared as "Supporting Success" in the Fall 2022 issue of Independent School.

It’s been said that equity and inclusion work is not just hard work, it’s also heart work. In independent schools, this heart is often embodied in the role and responsibilities of the diversity, equity, and inclusion (DEI) practitioner. I’ve worked in independent schools for 20 years, serving as a diversity practitioner for the majority of that time in five different schools with different grades and divisions, and I know firsthand that this adage is true. I have experienced the successes and challenges of this work, and I also know that perhaps the single most important factor for success is the relationship between the head of school and DEI practitioner. Not only does the head of school set the tone for a school’s DEI work, they’re also ultimately responsible for supporting DEI directors whenever inevitable challenges to their work arise.

And arise they will. As the past few years in particular have shown, challenges have been frequent, taken many forms, and come from all angles. As schools have navigated this, many have sought to deepen their commitment to DEI work, and many more still are building and expanding their DEI teams and initiatives. And as they move forward with this work, it’s never been more critical for heads to cultivate the kind of “head-heart” partnership that will allow them to more successfully interrupt resistance and offer support.

To do this well, heads of school must set up the DEI practitioner role for success, with appropriate titles, compensation, budgets, reporting structures, and so on, but they must also understand the challenges practitioners regularly face. They must know the scenarios that often come up and how to show solidarity, communicate with the school community, and stand up to the resistance and address the challenges DEI practitioners experience today. 

Common Scenarios

In my experience, there are several consistent challenges DEI practitioners face that heads must play a role in mitigating.

Justifying the right to exist. Despite the role becoming more common, some community members, including colleagues, parents, alumni, and trustees, still question the value and necessity of the DEI practitioner role and scrutinize the person in the role. DEI practitioners should not have to justify the existence of their role; shouldering this burden takes time away from accomplishing other work—particularly with faculty members and students. 

Heads of school must actively communicate—in person, in writing, and at all possible opportunities--—the necessity of the role and its connection to the institution’s well-being as both essential and mission-critical. Whenever heads of school speak publicly at events—and not just DEI-specific events but all-school meetings, faculty meetings, or parent receptions—they should explicitly state the value of diversity in their remarks. That said, heads should also make it a priority to be present at DEI events. Their presence publicly demonstrates their support and signals that they are a partner in this work. They should always speak at DEI events as well, making certain to acknowledge the practitioner’s efforts. When writing to the community, including  parents and alumni, they should similarly espouse the value of DEI and shine a spotlight on the practitioner’s works. This communicates that the head is both knowledgeable about the office’s accomplishments and visibly supportive of DEI’s importance to the school.

Getting a seat at the table. It is a head’s responsibility to ensure a well-designed DEI position that gives the person in the role access to all the information necessary to execute the role—a literal seat at the table in all necessary meetings and conversations. If the DEI practitioner has responsibility for student life, the head must make sure they participate in all meetings pertaining to student life. If they’re responsible for teaching and curriculum, they need to meet with the school’s department chairs and academic leadership. This helps ensure that the DEI practitioner is knowledgeable about what is happening within the institution and places them in direct contact with other school leaders who are responsible for specific areas of school life.  

It also allows them to bring their expertise to bear in these conversations. Are academic decisions failing to consider the impact on different populations in the community? Which students are represented in the highest-level courses? Are certain segments of the student population overrepresented in disciplinary efforts? These are the types of questions that a DEI practitioner can help raise and draw others’ attention to. I have often been the one to raise these concerns, which were either previously unnoticed or unacknowledged by other school leaders.

Having a voice but no vote. Many DEI directors are expected to have influence within various aspects of school life, but other administrators are ultimately responsible for taking action in that particular area. Although DEI directors are expected to work with student life, for example, the dean of students typically makes the decisions. Although DEI directors are expected to help with admission to ensure a diverse student body, the dean of enrollment makes the decisions. DEI directors need voice, influence, and authority in the form of decision-making power. Without decision-making power, they’re simply advising or making recommendations—recommendations that others can choose to accept or disregard. 

Heads must consider how to empower DEI directors to work collaboratively with other leaders and must ensure all school leaders approach their work with an eye toward diversity, equity, and inclusion. For example, a dean of faculty may frequently be the school’s chief hiring officer, reviewing the incoming applicants and résumés to decide which candidates advance in the search process. Perhaps the DEI director could similarly have access to all applicant résumés, selecting candidates that they believe show promise. In my experience, bringing a DEI lens to candidate selection advances candidates of color or other candidates with DEI experience in the interview process compared to when the dean of faculty alone reviews applications.

Lack of shared responsibility. One of the reasons some school leaders cite for not having a formal diversity practitioner role is the misguided idea that having a single diversity director will somehow unintentionally suggest that DEI work is solely that person’s responsibility. Although there is a certain understandable logic to this, this same logic is not applied to other areas of school life. For example, all school members are responsible for representing the school to prospective students and families, yet most schools still have a director of admission. This notion of shared responsibility must apply to DEI work as well. 

It can be tempting for school leaders to send all diversity-related concerns to the DEI director. This is certainly easier than admitting that other leaders are either uncomfortable addressing DEI-related issues or lack the necessary cultural competency to effectively resolve them. Ultimately, it is the head of school’s responsibility to ensure that this abdication of responsibility does not happen. Leaders can do this by holding all members of their leadership teams accountable for DEI work in their areas of responsibility. 

Rather than the DEI director being solely responsible for bringing DEI-related professional development to the faculty, expect the dean of faculty to view this as a part of their work as well. Rather than the DEI director being called in to address student life issues that involve students of color, expect that the dean of students will be capable of successfully navigating these situations. How has the college counseling office successfully attended to the college placement of students of color? How has the athletic department worked to ensure locker rooms are safe places for LGBTQ+ students? When members of the school leadership team submit their annual reports, consider asking them all to reflect on how they have identified and addressed issues of access and equity within their areas of responsibility. These are examples of ways to set explicit expectations that all school leaders view this as part of their work.

Hyper-scrutiny and circumvention. Too often, community members undermine or outright disrespect DEI practitioners. This disrespect can take many forms, and in my experience, hyper-scrutiny and circumventing are among the most frequent challenges.

This occurs when trustees, parents, or alumni appoint themselves as overseers of the DEI practitioner’s work. Sometimes it is framed in a positive light (“I’m trying to help,” or “I want to be involved”), but this hyper-scrutiny is ultimately a way of asserting dominance and attempting to wrest control. Other times, people go to other administrators for action in areas that are within the DEI director’s purview. This can happen before, after, or instead of communicating with the director directly—each of which carries different frustrations and implications. Connecting with other administrators before speaking with the DEI director undermines them, particularly if other leaders respond differently than what the DEI director says. Connecting afterwards suggests that they don’t have to listen to the director or respect their decision. 

In situations when someone has circumvented the DEI director, heads (or any other administrator) should immediately refer that person to the DEI practitioner to speak directly. If the reason they are approaching the head is for an appeal, heads need to affirm that the director’s decision in the matter. If the head disagrees with the director, they should seek to better understand the director's position before undermining their authority in front of others. Lastly, heads can let the individual know that the matter is resolved, and that they expect not to hear more about it. If that response is not accepted, then heads might need to invite them to pursue other options. Independent schools are communities by choice. You cannot abide individuals in your community who actively undermine members of your leadership team, especially those from historically underrepresented and marginalized groups.

Being a Champion

Heads of school must be willing to empower, defend, and champion the DEI director and their work. They must publicly and frequently address the community and shine a light on this role and the work. And they might need to have some difficult conversations with constituents. But this does not in any way suggest that DEI directors need rescuing or are incapable of speaking on their own behalf. Despite DEI directors’ best efforts, there will likely be times when different stakeholders refuse to accept their authority and position.  

To be clear, heads of school are not the DEI practitioner’s savior. The head’s role is to remove obstacles from the DEI director’s work whenever they are unable to do so themselves. Sometimes this requires linking arms with them in partnership; sometimes it requires standing behind them to support; and sometimes, it means getting in front of them—serving as a shield and receiving the brunt of the attack as they take detractors head-on. Most of all, the DEI director must know and feel that the head is unquestionably in their corner to have a successful partnership.

James Greenwood

James Greenwood is dean of diversity, equity, and inclusion at Western Reserve Academy in Hudson, Ohio.