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!
Your background
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.

Your family
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...