Dr. Winston Sakurai is Principal of The Prep at St. Andrews School in Honolulu, Hawaii. He was named 2016 @NASSP National Digital Principal and 2016 HASSA Hawaii Principal of the Year, and is moderator of the Twitter chat #PrinLeaderChat Sunday evenings at 9pm ET for all school leaders.
I’m so fortunate to have worked with Winston at St. Andrews School and with so many awesome educators. After learning more about all the innovation that is happening in Hawaii and at his school. I really wanted to share his story with you. Aloha!
I was born and raised in Hawaii. I grew up on the windward side of Oahu. My parents understood the value of education. They moved from Honolulu to another part of the island where the school system was really good to put education first. They would say that they didn’t want me to have to work as hard as they did. They had to do a lot of manual labor and didn’t go to college. My dad repaired air conditioning units. My mom would get up at 4am as a cafeteria worker at the high school down the road. They put every effort into their children’s education so I could go to college and do well.
It’s a great story. My wife, Rochelle, and I have had the opportunity of working together as educators in the same schools since we began. She has been a kindergarten and 6th-grade teacher, early childhood and then with our middle school and high school and past ten years before I was here at the Prep, she was the college counselor and I was the principal for the middle and high schools in the upper school. We worked together as a team. We call it “Team Sakurai.” She’s now the college counselor at the Priory at St. Andrews Schools. Her office is right down the hall from where I am.
Rochelle makes me better. I appreciate her because she is smarter than me and she does a lot of things that point me in the right direction. We have two children. I am fortunate to be the principal for my son, Matthew, who is in fourth grade and my daughter, Madison, is in first grade. Not every educator gets the chance to develop a school that your children will go to and benefit from. Even though we are working together as a team, we also get the benefit of seeing our children having those experiences that we create for all children here. I’m very blessed to have this opportunity.
What it was like for you as a student
I did have a little bit of a struggle. I remember third grade and taking the standardized assessment tests and scoring really high. But they wouldn’t put me in the Gifted and Talented Program because my grades in school were just average. I didn’t do well on everyday work because it was kind of confusing. Math was easy. English was a struggle.
My mom asked the school for diagnostics about speech delays and impediments. Through the testing, they couldn’t find anything. In 1983, I made it through because my parents purchased a Commodore 64 for me. It had a spellchecker and a word processor so I was able to get through school.
[This is Barbara: make sure you listen to more about how technology and his mom helped him starting around 14:00]
It wasn’t until later when I was in college and couldn’t get through the foreign language class that I found I had dyslexia. I’m thankful for the University of Hawaii who understood that there are ways to get through college even through struggles with language acquisition. I remember what Mrs. Ito from the student services center said to me, “I can help you.” That was the support I needed.
Voice of Reason on the Hawaii state board
In 1993 at the age of 20, I was appointed by Governor John Waihee to the Hawaii State Board of Education and served multiple terms as Vice Chairperson. I helped to create the BOE’s Committee on Budget and Fiscal Accountability where he redirected hundreds of millions of dollars in wasteful spending back to schools. I was known as the BOE’s “Voice of Reason” during my ten-year tenure, My accomplishments include blocking privatization of public schools, stopping class size increases, and negotiating a settlement to the statewide teacher’s strike.
I would also serve as a voting member on the National State Boards of Education Association and National School Boards of Education. In 1996, I was named by the Honolulu Star-Bulletin as one of 10 people “Who Would Make a Difference in Hawaii’s Future” along with notables such as Governor Ben Cayetano, US Senator Mazi Hirono & US Representative Mark Takai.
Your journey as a teacher and becoming an administrator
I “retired” from the BOE to teach History at Hanalani Schools and spent five years as the elementary administrator before becoming principal of Hanalani’s Upper School in 2008. During my tenure, the school developed an international championship robotics program, national award-winning student government, National Honor Society chapter national recognized for service, raising Advanced Placement (AP) passing exam scores and a college readiness program where 100% of graduates are accepted to college.
Award for National Digital Principal in 2016
My wife was the one who had me apply for the National Digital Principal award. I told her that I’m not anybody and not at that level that everyone else is. I remember that Eric Sheninger won the award in 2012 and I thought I would never be like him. She told me every single year, that I was good enough to apply. It took a lot of her encouragement helping to develop who I am that brought out the best in what I could do. I was one of three digital Principals of 2016. Here is a picture of me with Bobby Dodd and Glenn Robbins.
Principal at The Prep at St. Andrews School
The Prep, a school within St. Andrews School, is four years old and an all-boys school right in the heart of Honolulu. We’re trying to make it one of the most innovative schools in the state. For a principal to have the opportunity to build a new school is unbelievable. Currently, we’re kindergarten through 4th grade and we hope to continue growing. Even now we’re talking about what to do for our incoming 5th and 6th graders and beyond. We’re building a school with great teachers and the sky is the limit. Having to build things on our own, we have to think creatively and outside the box. Everything is new each year. Follow #WeThePrep on Twitter. Technology brings students together at The Prep.
Design Studio 4
We’re using the design thinking process from Stanford that places a focus on empathy. Our students are building things here on campus and creating different spaces for learning to take place. The kids own the process. Having them think about others and not themselves, being empathetic, understanding people is a process that will help them become successful. They problem-solve, create, iterate, test things out, iterate again until things are right. That’s how life is. We teach them that you don’t fail until you stop and quit. We encourage them to keep on going, going, going and make it better. When you stop because you’re giving up, that’s when a failure takes place. But if you iterate, iterate, iterate, you’re constantly getting better and moving forward, you’ll be very successful for the rest of your life.
It’s hard. We’re in a world where we have to understand each other. In order to understand each other in a way that you’re very helpful to each other as well. It’s not just taking something and saying, “I get it.” It’s about what we can do to help that other person be successful as well. Give them opportunities. Help them to be better. Our society will move forward and get better because we’re looking out for each other, trying to help each other move to the next level. We get the opportunity of knowing that the next generation is going to take our nation to a different place that is so unique and so spectacular that we couldn’t even imagine those things.
Why are you so passionate about changing school?
I see that lightbulb go on that they wouldn’t see if they were reading out of a textbook because it wasn’t relevant to them. My son comes home sometimes and asks me “what’s the relevance of this worksheet?” I have to question that, too. Now, he doesn’t say that as much. He goes, “this is difficult, but I think I can figure it out.” Which is spectacular!! It’s such a difference in how he’s learning and how he’s doing things because he’s processing stuff because he wants to. He thinks the challenge is important to tackle and fix.
Dr. Winston Sakurai has distinguished himself as an innovative educational leader at the state and national level for over 25 years. He was recently named by the National Association of Secondary School Principals as a 2016 National Digital Principal of the Year and by the Hawaii Association of Secondary School Administrators as the 2015-16 Hawaii State Principal of the Year. He currently moderates a national education chat for school leaders, #PrinLeaderChat, on twitter.
Winston’s Contact info
Winston Y. Sakurai, Ed.D
NASSP National Digital Principal
Former Hawaii State Board of Education Vice Chair
The Principal of The Prep, St. Andrew’s Schools
- Website: http://winstonsakurai.weebly.com
- Twitter: @winstonsakurai
- Twitter chat: #PrinLeaderchat
- Facebook: https://www.facebook.com/pg/winstonsakurai
- LinkedIn: https://www.linkedin.com/in/winstonsakurai
New Book: Education Write Now: Top Strategies for Improving Relationships and Culture with multiple authors including Dr. Winston Sakurai
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