Teacher Feature⼁Introducing Olivia O.
At Pacific Preparatory, we are so lucky to work with the most thoughtful and inspiring instructors, all who bring lessons to life with engaging connections to student interests and their community. This month, we are excited to celebrate Olivia!
Meet Olivia (she/her)! Olivia is an experienced educator with a passion for helping students build the habits and skills they need to thrive both in and out of the classroom. She holds a B.A. with Honors in Psychology from Pitzer College and an M.S. in Learning Design and Technology from Stanford University, where she focused on the science of learning and designing effective educational experiences. As a certified Executive Functioning Coach, Olivia has supported students from elementary school through college, blending research-based strategies with personalized guidance. Her approach centers on empowering students to develop strong systems, boost their confidence, and foster independence, ensuring they have the tools to reach their academic goals and beyond. Olivia is a native of the Bay Area, where she still lives. In her free time you can find her either outside adventuring or on the couch knitting.
What initially drew you to working in education, and how did you transition from special education and Applied Behavior Analysis (ABA) therapy to executive function coaching?
I was first drawn to education through Jumpstart, an early literacy program I worked with in college, where I spent time in preschools with children who hadn't yet formed any idea of themselves as learners. Watching four-year-olds light up over books made me think hard about what happens later — how so many students start out curious and excited, and somewhere along the way lose that. I graduated with a psychology degree, and went on to work in special education and ABA therapy. But I found those systems more constraining than I'd hoped. My training was deficit-based rather than asset-based, and while ABA has real benefits, it can be narrow in how it understands children with Autism. These jobs became especially challenging during the pandemic, when I found myself trying to teach social skills to masked, socially distanced three-year-olds. And at the same time, it was clear that middle and high school students needed more support than ever as they transitioned to online learning. So, in May of 2020, I started a private tutoring practice.
I stumbled into EF coaching almost by accident. I was tutoring three students in humanities when I noticed that none of them was struggling with what they thought they were. They came to me for help with English, History, and Spanish — but what they actually needed was help organizing their lives. They weren't confused about the content, but they all struggled with starting tasks, finishing them, and staying organized, and had piles of completed work that had not been submitted. These were smart, motivated students, and they were failing school. I brought this pattern to a mentor, and she introduced me to the piece of the puzzle I hadn't known I was missing: executive functioning.
What do you find most fulfilling about your work in EF support, and how do you help students develop confidence in their academic abilities?
The most fulfilling part of my work is helping students change the way they see themselves. When you have struggled with EF challenges for a long time, chances are people have become pretty frustrated with you — and often the blame is misplaced. The student is seen as “forgetful”, “lazy", or "unmotivated" when really, their brain needs a kind of support it isn't getting. And if a student has in fact stopped trying, that's usually because years of negative academic experiences have eroded their self-esteem. We don’t talk about EF skills in school, and students with executive dysfunction tend to be overlooked and struggle to explain why everything feels so much harder for them. The more I learn about EF, the more I'm convinced that what these students need is not an attitude check or stricter rules at home, but for someone to help them develop skills that don't come naturally, and, most importantly, to believe in them.
A few years into coaching, I decided to go back to school to learn more about learning. I enrolled in Stanford's Learning Design and Technology master's program, where I deepened my understanding of how different brains engage with material and developed approaches tailored to different types of EF challenges. For students who struggle with time management, I have them become "time scientists," timing their daily activities to sharpen their awareness of how long things actually take. For students overwhelmed by deadlines, we put due dates on large wall calendars that stay in view all day. For bigger projects, we break them into weekly milestones and use Google Drive folders to track works-in-progress. These aren't one-size-fits-all fixes, they're tools I adapt to each student. And when a student starts using them independently, that's usually when they stop feeling like something is wrong with them, and start feeling like they finally have a system that works for them.
What are some key differences between tutoring subject-specific content and providing executive function coaching, and how do you balance both in your sessions?
To me, the biggest difference between tutoring subject-specific content and providing EF support comes down to transferability. The content knowledge and skills that students need to succeed in a particular subject are often unique to that subject — and while helping students grow their competence and confidence in specific subjects is important work, the goal of subject tutoring can be limited in scope: help students improve their understanding so they can perform well in a specific class. That knowledge doesn't always travel.
Executive functioning skills don't operate in the same silo. These skills are at the root of success across subjects, and when students develop habits and systems that help them manage their work more effectively, the benefits tend to be widespread and cascading. That's what makes EF coaching feel like such high-leverage work. That said, I find that teaching EF skills is much easier to do in the context of specific tasks than in the abstract. I can explain how to break a project into smaller steps, but it lands completely differently when we're doing it together with a real assignment and a real deadline. In practice, I rarely separate the two in my sessions — we use the subject material as an entry point to get to the deeper EF skill.
