Interview with Mrs. Walker-Oakes, Head of School – Lessons, Goals, and Memorable Moments


Photo courtesy Flintridge Prep

Image of Mrs. Walker-Oakes, Flintridge Prep’s Head of School

This July, Mrs. Vanessa-Walker Oakes became Flintridge Prep’s new Head of School. Mrs. Walker-Oakes has been a valued member of the Prep community for 18 years, serving as a beloved teacher and Assistant Head for Student Life. During her time at Prep, she has also served as Senior Class Dean, a Grade Level Advisor for 7th and 9th grade, Director of College Counseling, and Dean of Faculty. In addition, she has been a member of the Admissions Committee for 18 years. Mrs. Walker-Oakes and her husband, Dan, have four sons; two are Prep graduates, and one is a current Prep student. We spoke to Mrs. Walker-Oakes about how she came to teach at Prep, her goals for the school, and lessons she’s learned from the past.

Audrey (A): What were you like as a teenager and what were your interests?

Mrs. Walker Oakes (WO): I was very fortunate. I attended a school that was a lot like Flintridge Prep, and so, it was wonderful. I loved my teachers, and I had great opportunities in class and outside class. I was a swimmer. I was interested in visual arts. I was interested in student government. I was involved in Junior State. I was in an environment like Prep where you could do all those different things, and you didn’t have to focus on only one. It was really welcoming, so I really loved my high school experience. I think that’s part of the reason I was drawn to working with this age group, because it was a wonderful time for me and I want other young people to have that same experience. 


A: How did you decide that you wanted to be a teacher?

WO: It may sound strange, but if  you asked me in second grade what I wanted to do, I would have told you I wanted to be a teacher. I loved my teacher. I loved everything about her.  

Then as I went through high school and college, I started to pursue other things. I was interested in a career in medicine, particularly a career in psychiatry. I went to medical school for a year, but I found myself really drawn to other issues outside medicine, such as human development, history, art history. I was drawn to the idea of trying to make the world a better place through educating and helping young people, not so much through medicine but in other ways. So, I went back to graduate school in art history, planning a career in university teaching. I came to Prep thinking, “I’ll work here for a few years, and then I’ll finish my degree and hopefully enter college teaching,” but I totally fell in love. The first day I stepped into a Prep classroom, I was teaching 9th grade World History, and I thought, “This is my destiny, and I didn’t know it all those years! This is my place, these are my people.” I realized adolescence is a really special time in young peoples’ lives, and it’s a privilege to share this journey with students.

Looking back now I ask myself, “What took me so long? What was I doing with all this other stuff?” But no education is ever wasted. I’m so glad I got to have all the adventures I did.


Thomas (T): So that leads into our next question really well, actually. How did you come to teach at Prep? 

WO: While I knew that I was interested in education, my husband is an orthopedic surgeon, so we had been living through his training for a long time with two small children. We had gone from Boston to the LA area to living in Minnesota for a year. I honestly came to Prep originally because I wanted stability for my boys. My oldest son went to four schools in four years. It was wild. 

I was drawn to the warmth of the Prep community, and then when I came here, I decided I had to stay. I remember my first year, someone in grad school said, “Are you going to come back and finish?” because I hadn’t finished my dissertation, and I said, “No, I’m more challenged at Prep than I’ve ever been anywhere else.” My students push me every single day, but they’re also so warm and generous and wonderful and curious. My colleagues are amazing. Walking into the faculty room at Prep, no matter what the day is you’re going to get an amazing conversation: politics, culture, maybe an introduction to the most bizarre and challenging board game you’ve ever seen. I found it a very inspiring community, with a lot of ambition to do good in the world. I liked feeling I could be a tiny part of facilitating that.


A: What are some lessons you’ve learned throughout your years teaching at Prep?

WO: Humility (laughs). My students have definitely taught me that. They ask questions I can’t answer, they really push me to think differently. It’s taught me to be humble and to be curious all the time about how others might see the world differently. 

I really learned a lot at Prep through failure, too. I’ve had some failures at Prep, some pretty spectacular, some less so. But if a lesson doesn’t go right the first time, you can say, “I’m sorry. I totally saw this playing out differently, but we’re going to try again tomorrow.” I feel like I’ve learned a lot about how to be a better teacher by having the opportunity to try things, to get feedback from my students and my colleagues and to grow, but I’ve had to get more comfortable with that. Because if you try to do anything well, especially teaching, you’re going to have to take some risks and they don’t always work out. So, humility. Curiosity. Resilience. You’ve got to stick with it even when you fail the first time.


T: In what ways has Prep changed since you first came? 

WO: Oh my goodness, Prep has changed so much. I would say there’s this core that’s very constant, which is an emphasis on exceptional teaching and learning, and really valuing relationships. But beyond that there’s been so much change. 

When I came to Prep, the performing arts center had just been built. This whole amazing performing arts curriculum that we have was all growing and developing during my 18 years here. Our visual arts program has grown by leaps and bounds. We did not have things like the Bachmann Collaboration Building. We didn’t have the library when I first started here. The library is such a hub — that ground floor is just so Prep. Students are gathered around working on math problems and playing board games and talking to one another, surrounded by art on the walls. But those places weren’t here before, and so I think the intellectual and creative resources for students have grown a lot, and you see that in the sophistication and the opportunities that our students have now. Not that they weren’t great when I first started, but there’s a lot more opportunity, and the faculty are really committed to making those opportunities available.


T: Now that you’re finally Head of School, how does it feel? 

WO: I feel really, really fortunate. I don’t have a better answer than that. I feel really lucky to be able to do work that matters to me and to support a community that is so supportive of me and of each other. I’ve grown an unbelievable amount in the 18 years I’ve been at Prep, and I would imagine I have a lot more growing to do, too. 

I care very deeply about this community not just at a professional level, but at a very personal one. I think there’s so much exciting growth ahead for Prep, and I think it’s going to be really interesting throughout your journey as students here. We have such a committed faculty, staff, and student body. 


T: What are your biggest goals in terms of the upcoming school year?

WO: For this school year, we have a couple really clear focuses. At an institutional level, we’re looking at embarking on a strategic planning process that will take us through the end of the next calendar year, as well as really working to define and integrate our DEI Initiative.

We also have a profound commitment to seeing our community through the transition back from this pandemic by creating connection and relationships. If you look at the things that we’re creating and building, the new Center for Student Life and the new facility adjacent to the gym to promote health and well-being, as well as all our new faculty and staff (our learning specialist, school counselor, assistant athletic trainer), these are ways we are working to support students ever better. Our biggest goal for this year is to help our students, faculty, and staff transition back in positive ways and make sure you are supported. 


A: What do you see as the biggest challenges for Prep and how do you plan to address them?

WO: I think there are challenges and opportunities. We’re looking at a world that is growing and changing very quickly, so really thinking about what meaningful and powerful learning looks like going forward is a challenge but also an opportunity. If you look at the kinds of learning coming out of our new Bachmann building, that’s pointing to ways that we can continue to deepen our curriculum, teaching, and learning, as well as build more connections for our students to the world outside Prep.

Our Global Studies, Leadership, and STEAM Initiatives are pointing us in creative, collaborative directions. I do think growing our work to meet the demands of a diverse, evolving world is a big challenge and opportunity that we’re all ready for and excited about. 

And I think also rebuilding relationships is especially important, coming back to Prep after the last two years. It’s no small task. It’s not going to be fixed in four weeks. There were huge gains in the last year –– I think students had to be resilient and develop life skills and independence way beyond what happens in a normal year. But that also came with some difficulties, so it will be a goal to really think about how to support the mental health and well-being of students going forward.


T: During online learning, we saw shifts in curriculum towards project-based learning with less exams. As an institution and on a general level, will the curriculum be tending towards that direction, or will things be returning more to what they were like pre-COVID?

WO: I think that we are evaluating where the changes that were implemented last year were really to the benefit of powerful and meaningful learning for our students, and where we had to make adaptations that weren’t necessarily to students’ benefit. There were changes I made in my classes I’m definitely keeping, because I think they were positive for my students. 

Our student life committee andour academic life committee are intentionally examining things like: “How do we assess students?”, “What should midterms look like?”, “How do we move forward taking the best of last year, and keeping it?” 

I don’t think anybody thinks that schools are going to go back to the 2018 “lock, stock, and barrel”. No one’s going to do that because we had to adapt and there were silver linings in that (laughs). They didn’t always feel like silver linings as we were living them, I would imagine, but there were.


A: As a Prep teacher and a Prep parent, in what ways does that impact your approach to leadership and teaching? 

WO: I do think having had the opportunity to be a parent in this community and watch my children go through the program gives me insight into the developmental experience of Prep and how parents feel at different points in the journey. I’m really grateful to have that opportunity to see our program from at least three different sides, from a teacher’s perspective, an administrator’s perspective, as well as a parent at home. It has been positive feedback for me, offering an awareness of the student experience. 

I do think as a leader though you have to be very careful to have boundaries between the experience of one’s singular child and what is in the best interests of 530 children and all of their families, the faculty and staff involved, and alums. Prep is a big community. And so while I’ve been very grateful for the perspective my children offer and the fact I’ve gotten to live the Prep journey with them, I always do try to be careful about making sure I don’t overgeneralize what my childrens’ experience might have been.


T: You’ve shared that you want to prioritize connection, especially after coming back from COVID. How do you envision students approaching this and what actions will the administration take to promote that?

WO: To promote connection? 

T: Yeah.

WO:  As a faculty, staff, and administration, we’re focusing on connection in our planning and decision making, looking at things like expanding our advisory programs. This year we don’t just have 7th and 9thgrade advisory. We have 8th grade advisory for the first time. In the coming year we will offer advisory to all grades, creating a space within the week that is really dedicated to students’ well-being and connection and reflecting on identity. I think that with our new school counselor and learning specialist we have resources available to students outside the classroom to support them and to foster connections, through one-on-one meetings and by offering group workshops.  

The school is also looking at student events, things like outdoor education and the class events that we put on. We want to host these student events this year because many of them couldn’t happen last year. But we are also considering how we grow and change our programs and events to foreground connection and align with our mission and initiatives. For example, we’re doing the family barbecue, bringing back beloved traditions, but also growing those traditions in ways that hopefully are more inclusive and reach our students in new ways. We’re trying to be really intentional about that goal.


A: What has been your most memorable moment at Prep? 

WO: One of the things I’ve been touched by most in this community is that when there is crisis, when someone or everyone is coping with something truly painful, this community comes together in profound ways. I think of those times when we’ve lost someone dear, when there is tragedy. In those moments this school really does absolutely everything it can to support and ensure that we can move forward, together. We must find ways to hope even amidst tragedy, and those are the moments that speak most to Prep for me. 

There are wonderful moments of course, such as promotions and graduations, family barbecues, proms and musicals. But life has challenges, and we show who we are and what we believe when we’re challenged. This community really does come together in both the good and the very, very hard times. There is a drive here to do good, for Prep and for the wider community, too.


T: On a lighter topic, a lot of people have been asking, will the new schedule stay? 

WO: We’re definitely thinking about the schedule and evaluating the experience this fall because we’ve never lived this schedule in-person. I think it’s probably unlikely that the school would go back to seven, 43-minute periods a day again, at least right now. That’s just not what is currently regarded as best practices in education and what’s in the best interest of students’ deep learning and wellbeing. 

We are continually reflecting on the schedule, though, and considering what’s the right balance of class time, free time, and co-curricular time. We will keep you posted!


A: In 20 years, what would you most want to be remembered for as Head of School?

WO: I’d like most to be remembered as someone who listened to the hopes and needs of this community and facilitated the school reaching its vision and its dreams. One of the most wonderful parts of leadership is being able to listen to people and hear how they believe they will thrive, and then having the opportunity to help make that happen.

I would love to be able to look back and say, “This school had a mission to be a place of incredibly powerful learning that respects the developmental processes of childhood and cultivates a sense of meaningful purpose and responsibility to others, and then we worked, always, to create that experience for young people in an ever-changing world.”

Prep has a lot of opportunities to create our next generation of leaders. Prep students go out in the world and lead in wonderful ways. This is a world that needs creative, curious, compassionate leaders. So my goal is to imagine: how do we help you all be the best leaders you can be? That’s a real ambition.