Waiʻanae Elementary School Principal Sheldon Konno has been named the 2026 recipient of the prestigious Masayuki Tokioka Excellence in School Leadership Award, recognizing his commitment to strengthening school culture and expanding support for students and families in the Waiʻanae community.
The annual award honors outstanding Hawaiʻi public school principals who demonstrate visionary leadership, a commitment to student success and meaningful engagement with their school communities.
“It’s very humbling to be recognized, and that the community at large sees the vision of what we’re trying to do at our school, to not only support our kids but the Wai‘anae community as a whole. It helps to ground us even more,” said Konno, who is in his fifth year as principal. “It’s definitely a kākou effort. I wouldnʻt be able to stand here and talk about our vision and what we’ve done if it wasn’t for the team at our school.”
Under Konno’s leadership, Waiʻanae Elementary has focused on building strong relationships with families, fostering a supportive school climate and ensuring students have access to the resources they need to succeed both academically and socially.
Sponsors Island Insurance Foundation and King’s Hawaiian awarded Konno a $25,000 prize — including a $10,000 personal cash award and $15,000 toward a school project of his choice.
Konno plans to use the award funds to expand Waiʻanae Elementary’s community resource center, which provides critical support and services to students and families in a community impacted by socioeconomic challenges. The resource center operates within the school’s Seahorse Community Hub, connecting families with essential resources and helping remove barriers to student learning.
“It’s important that we bridge community and the school, because our job is to serve the community. If we can really intertwine that, we’re more aware of what the needs are because we see it — we see it every day,” Konno said. “In order to be successful in educating our kids, we have to support and educate our parents and grandparents to meet their needs so that we can move education higher on the priority list.”
The Tokioka Excellence in School Leadership Award honors the late Masayuki Tokioka, founder of Island Insurance Company, Ltd., and a proud graduate of Hawai‘i public schools. The award was announced April 2 at the Public Schools of Hawai‘i Foundation’s annual banquet held at the Sheraton Waikīkī.
“Anybody that’s running an organization is a CEO — they really are the heart and soul of the organization. The role that they play is critical, and the more that we can highlight schools that are doing things well and innovatively, the more it will help the community, their students, and all of us in the end,” Island Insurance Foundation Chairman Tyler Tokioka said.
Konno was selected from a competitive pool of nominees statewide. Two semi-finalists were also recognized — Christopher Bonilla, principal of Holomua Elementary School, and Adria Medeiros, principal of Mountain View Elementary School.
In all 15 HIDOE principals — one from each complex area — were honored as nominees for the award. This year’s nominees were:
- Ryan Amine, Mayor John H. Wilson Elementary School
- Michelle Barber, Waikoloa Elementary and Middle School
- Christopher Bonilla, Holomua Elementary School
- Richard Carosso, Lahainaluna High School
- Alvan Fukuhara, Waipahu Intermediate School
- Wayne Guevara, ʻAiea High School
- Kendrick Kakazu, Major Sheldon Wheeler Elementary School
- Sheldon Konno, Waiʻanae Elementary School
- Jennifer Luke-Payne, Kaʻaʻawa Elementary School
- Adria Medeiros, Mountain View Elementary School
- Fig Mitchell, Kīlauea Elementary School
- Ervin Pasalo, Hōkūlani Elementary School
- Noel Richardson, Enchanted Lake Elementary School
- Timothy Shim, Pōmaikaʻi Elementary School
- Travis Toriano, Hilo Intermediate School
