Women run about 30 percent of the country’s 500 largest school districts.
Whitney Oakley, the superintendent of the 68,000-student Guilford County public schools in Greensboro, N.C., is one of them.
Oakley stepped in as an interim superintendent in July 2022 to replace Guilford’s outgoing leader, Sharon Contreras, as the system embarked on spending a $1.7 billion school bond, the largest in the state’s history, and tackling three key priorities: school safety, academic recovery, and student mental health.
She’d served as the district’s chief academic officer before applying for the top job—a role she was encouraged to pursue.
Oakley spoke to Education Week about her leadership journey, navigating professional and personal duties, and how K-12 can steer and support women—who make up the majority of the education workforce—into leadership positions. The interview is part of a series conducted with women education leaders during Women’s History Month.
This interview has been condensed for length and clarity.
You’ve always wanted to be a teacher, from what I’ve read. What drew you to education?
A lot of it is the women I encountered along the way. I definitely knew I wanted to be a teacher after my very first day of school, as a kindergartner, which was here in Guilford County. I remember as each student was walking in, even on the first day of school, my principal, whom the school is [now] named after—her name is Doris Henderson—knew all of our names. She had been studying and was able to greet us by name on the first day of school.
I just think that that kind of relationship … it’s had an impact on me my entire life. I think about it all the time when I think about leadership, and women, and how to make operations work, and how to help kids love school. So very, very early on I knew that I wanted to be a teacher. I didn’t know I would go on to be a principal, and I certainly didn’t think about the superintendency.
How did you make the decision to pursue leadership beyond the classroom?
There is certainly nothing more impactful than a classroom teacher, and anyone who disagrees just doesn’t follow the research. Great teachers have a bigger impact than anyone else.
But my mom is a social worker, and so we’ve always been very close. She made a lasting impression about the need to serve others. She did it as a social worker; I did it as a teacher. So as opportunities became available, I taught 1st grade, I taught special education, and then my principal came into my classroom and he said, ‘You know, you really have the skills to be an assistant principal. Think about how that would build up some of the teachers who are around you, who are your colleagues.’
These opportunities, these natural leadership opportunities kept coming about every three to five years. It was kind of a natural sort of trajectory. Then I thought about the impact I could make in my hometown, in my community, at which point I was a mom—and your vision changes a little bit when you are sending your own kids to school.
As I’ve been in central office, I’ve been able to see people like our board chair, who is a Black female and has served for decades, and has always served as a role model to me. And our former superintendent believed [in elevating women] ... She had a sign in her office that said, ‘Women supporting women, supporting women,’ and made it a very intentional effort to ensure that in her succession planning that she was investing in women as part of her legacy.
What supports did you receive as you moved from the classroom and into leadership that were instrumental? Were they readily available or did you have to seek them out?
There were opportunities that I had to seek out, like coaching. People lose sight of the fact that all professionals need some level of executive coaching. I continued to seek that out over time.
But what happened with the people who put me in the position was that they let me have a seat at the table. That’s not always true. Sometimes you don’t get a seat at the table until you’re in the job.
It’s such low-hanging fruit, in terms of leadership development, to think of succession planning and who gets a seat at the table and who does not. Often women in leadership do not get to have a seat at the table.
While the majority of teachers are women, the number of women declines as you move up the ladder. What can be done to increase the number of women in those positions?
I think it’s important to say the numbers are even worse for Black and Latina female leaders. I think that those numbers are staggering, and we are losing the ones that we have. To me, there’s a lot of responsibility there.
Half of the country’s largest districts had changes in leadership since the start of COVID. So there’s this turnover, and of the 94 women leaders who left the superintendent role, 62 of them were replaced by men, which means that nearly 7 in 10 women superintendents have been replaced by men.
System-level-wide we have to have clear career pathways for teachers, and as a country we haven’t really done a good job at that. There’s the teacher position, there’s the assistant principalship, there’s the principalship, but there are not these clear pathways like there are in the business sector for professional growth.
The profession itself, the teaching profession, becomes less and less attractive as time goes on just because of the things we’re asking people to do.
In North Carolina, a teacher with zero years of experience makes the same as an Uber driver, and think about the difference in the credentials needed to be a classroom teacher.
We need to think about advocacy and how we value the profession. Personally, I have a responsibility to make sure that the leaders in our organization reflect the students that we serve. We are nearly 70 percent Black in our school district and nearly 20 percent Hispanic. We have to make sure that we are hiring people, and coaching people, and developing people who look like the students we serve.
What advice would you offer for women who want to become district leaders and who may not have support in the system?
I think you have to lean into the work. You have to show up for things that sometimes you’re not invited to. When there are community meetings, [show up]. A big one is political advocacy, like being willing to make your name known when it’s time to vote on a budget, and calling elected officials, and thinking wider about the job. So the footprint gets bigger each time you navigate through the system.
People pay attention when teachers and principals mentor others and they are successful, too. It’s not just their own footprint and their own difference they are making, but how are they building up others?
So showing up, not just to the meetings that are required, thinking about advocacy and teaching others how to be advocates, and then asking, ‘Are there opportunities for coaching for me? Are there district resources or programs that could further develop my leadership?’
You have to show up for things that sometimes you’re not invited to.
You have to show up for things that sometimes you’re not invited to.
Then, depending on the community, there’s a place for a presence at county commissioners’ meetings, at board of education meetings. Learning the politics of the job is not covered in master’s programs or graduate programs or doctoral programs.
How did you navigate those personal traditional responsibilities with your professional duties?
I am still new to the role. I would not say I have it all figured out by any means.
I have an executive coach. I have made sure that the people who report to me also have access to that support. Part of the role of the coach I have is to talk about balance and complexities of the role and how we figure out the calendar to make sure that I can be good at all of the jobs and not let other things, like home life, be sacrificed.
For example, I try very hard to only do two evening and night-time engagements a week. I make sure that my son’s soccer games are protected time on my calendar. When I am at work, I am making sure that the way I am spending my time reflects what we’ve said our top priorities are. If the calendar doesn’t match the priorities, then there’s work to be done. That’s kind of how we’ve started.
It seems like some of the work has to be done by [women] because the system isn’t always set up to support them.
Yes, but you’ve got to be willing to ask for help. … I think that is sometimes hard for women because it’s a perceived sign of weakness. We have to create safe spaces where we do that and we do it in front of each other: as principals, as they are leading teachers, but also as they are helping to develop [their own careers], they need safe spaces where they can ask those questions, too. And [we need] women who are willing to model that.
It’s not a sign of being weak, it’s a sign of wanting to get better. Often the two can be confused if the climate is not right, if the climate is not primed for growth.
That sounds like it’s both a system and an individual responsibility.
Yes, we can model it for each. So people who have figured it out, can also just say, ‘It’s OK to say I don’t know the answer to the question. It’s OK.’ I don’t know that’s always a reality. So thinking about how to create those spaces where you can model the behavior … is really, really important and can be hard in work that is fast-paced and complex.
Why should school districts and the nation as a whole pay attention to the number of women who are serving in superintendent positions?
The work is complex, and there’s not this huge workforce ready to step into the job.
We know that the pandemic has been the most disruptive singular force in education in a century, but students are entitled to a [state] constitutional right to an education [in North Carolina] and so we have to lead during this very challenging time. Equipping women with the skills that they need to address learning loss, address national safety concerns, understand funding, understand how to address mental health and safety [is important].
Our whole country depends on a strong public education system, and if we are not thinking five years, 10 years, 20 years down the road about how we’re going to get people the skills they need to get into these jobs to be successful, it could undo an entire system.
