Leadership Lessons: 6 Reflections from a Millennial Woman of Color

Spring 2020

By Wellesley L. Wilson

I am a millennial, not because I received participation trophies as a child or because I enjoy avocado toast and disrupting industries in my free time, but because, according to Pew Research Center, I was born between 1981 and 1996. I’m also a black woman in a senior leadership position at my predominantly white school. It can be hard—and lonely—to exist in this space. Women are nearly 51% of the U.S. population. Women of color are 20% of the U.S. population but account for only 4.7% of CEO positions in S&P 500 companies. There are only three women of color who are CEOs of Fortune 500 companies; only one is black. 

The statistics on women leaders in my field of enrollment management and financial aid aren’t any different. A 2019 Enrollment Management Association (EMA) special report indicates gender inequality persists in our industry as it does in others. EMA found admission offices led by men are more likely to have more full-time direct reports than offices led by women. It also found that nearly 50% of male directors of admission and financial aid have an annual salary of more than $100,000 compared with only 30% of female directors. Senior leaders who are women are more likely to be paid less to do the same work as their male counterparts but with less support and, therefore, less time to think strategically about the critical work of enrollment management.

NAIS findings about female heads of school and heads of color are even more depressing. The 2018 NAIS report “People of Color and White Women in Independent School Headship,” found that a third of heads of school are women, a statistic that has not changed since the early 2000s. And although the number of heads of color has more than doubled in the past two decades, this group still represents less than 10% of the total population of heads of school.

After more than a decade in independent schools, including this one—my fifth school year as the director of admission and financial aid at Harpeth Hall School (TN), a place known for its well-articulated student leadership program and focus on building girls’ confidence—I’ve been reflecting on my journey. I’ve distilled my experience to six lessons and share it with others seeking leadership in independent schools, particularly young women of color.

Lesson 1

Volunteer and say yes. Take advantage of the opportunity to get to know your school beyond the scope of your job description. In my first admission job, I tried to learn as much as I could about independent schools and how they work. I kept my eye out for faculty committees and other school initiatives that could help me better understand my school outside of my stated responsibilities. I served on a faculty committee to overhaul the upper school adviser program; was part of the steering committee for the school’s reaccreditation; partnered with faculty to understand the data on upper school students and patterns of academic success; was part of the team that created and implemented a comprehensive student support program for new students who were also new to independent schools; presented at area workshops with our communications department; and launched targeted admission outreach events.

Once you establish a pattern of committing your time to serve your school, people begin to seek you out. By working with school leaders who had far more experience than I did, I learned how school decisions are made, how to navigate challenging student and family situations, how priorities are identified, and what specific work in independent schools appealed to me most. 

Lesson 2

Stay curious. Dive into professional development that will help you to stay sharp in your field, and that will sustain your sense of purpose. After five years and involving myself in as much as I could at my school, I began to feel restless. I’d noticed many admission and financial-aid conferences were signaling the importance of integrating marketing and communications into admission, and I thought learning more about this could be the key to revitalizing my energy. I decided to pursue a master’s degree in public relations and corporate communications; I loved being able to use what I learned in class in my daily work. At the end of graduate school, I saw my role in admission and aid through a new lens—I was ready for more responsibility, and, more important, I was recommitted to the work. Independent schools are dynamic, and your experience and knowledge should reflect a strong understanding of how education shifts.

Lesson 3

Be brave. Apply for the opportunities that speak to you. An often-quoted internal Hewlett-Packard report states that men apply for a job when they meet 60% of the qualifications, while women wait until they have met 100% of the qualifications. You don’t have to be part of this statistic. After seven years in my first job, I began the search process for a new role at a new school. It was demanding. Sometimes I felt like I needed to have no less than a million years of experience to get a phone call, and the search that led to my second and current position took two years. I spent countless hours researching schools to personalize letters of interest, participating in Skype interviews, and traveling for campus visits. I shed more than a few tears at the end of each unsuccessful hiring process. And yet, in hindsight, having the experience of being a finalist in multiple searches without being offered the position was a good thing. My greatest takeaway from that adventure is that clarity is critical, and bravery is best. It’s essential to fully understand why you’re in a search in the first place, what kind of community you want to serve, and how you want to spend your time each day. 

Lesson 4

Lead by listening. Listen to what your colleagues are and aren’t saying; seek out people to hear their perspectives if you’re only hearing one view or hearing nothing at all.

In my early days as a first-time director, I arrived with a flash drive with everything I thought I needed to be a good leader: notes from my previous school, notes from my graduate program, PDFs of articles from Harvard Business Review, presentations from conferences I’d attended, and research on my new school. I remain immensely charmed by my then 29-year-old self. What I needed to know then and understand now is how important it is to listen. Schools are big ships that don’t change direction quickly or easily, and you can’t steer it on your own. In graduate school, I learned how important the practice of active listening is; I’ve written the words “listen fiercely” at the top of my notepad in meetings ever since. It helps me remember to stay present and attentive to those around me. When I engage more people and listen, I make better decisions. I don’t always go with the most vocal opinions, but I’m intentional about creating space for people to share their thoughts. 

Lesson 5

People and relationships matter. Strong relationships with your colleagues are critical to your success and the success of your school. We all have job descriptions, but an essential and sometimes unwritten part of our job is to build connections with people. Good relationships don’t happen; they take continual work, so be deliberate. Ask how you can demonstrate that you appreciate the contributions of your colleagues and value what they have to offer. It may be spotlighting them publicly or one-on-one, visiting classes, going to athletic events, eating lunch together, or simply having a conversation. You will need these strong collegial connections when you have to navigate difficult student or school issues, and I’ve always had more productive meetings with people when the “tough conversation” isn’t the very first conversation we’re having. 

Lesson 6

Identify the people and activities that sustain you. I’ve found a group of educators in Nashville I can go to for guidance and laughter. I’ve met them through NAIS’s annual People of Color Conference, admission conferences, and long hours standing in school gyms during school fairs. No one knows the work of an educator better than another educator, and I’ve found it helpful to have people who know what I do, inside and out, but who don’t work at my school. I also have a mentor with whom I speak monthly. She has lived it before, and I’m grateful to be able to think out loud with her about my career. I’m open to any professional development experience that comes my way, and I share out what I learn. I try new things (submitting an article to Independent School magazine was on my “Very Big Bucket List”—check.) And I read, because sometimes the best way to recover from a hard day is to escape somewhere else.

Making the Move

Being a black woman on the all-white leadership team in my predominantly white school hasn’t been easy. I’ve had my ups and downs, I’ve questioned my skills, and whether I was indeed in the right position. But, more and more, I feel like the real deal. I credit the years I’ve spent doing this work, committing everything I can to be the best in this role.

It’s time for others to join me. I want to see more young women of color join me in leadership at independent schools. The independent school community needs smart, committed, and courageous people of color in leadership positions to help guide our schools if we intend to truly be relevant to students and families.

There’s no such thing as the perfect job, the perfect school, or the perfect time to apply. You may miss out on your opportunity if you’re waiting for everything to align. We are waiting for you; what are you waiting for?
Wellesley L. Wilson

Wellesley L. Wilson is the director of admission and financial aid at Harpeth Hall School in Nashville, Tennessee, and a previous co-chair of NAIS’s Annual People of Color Conference.