Trust nurtures a quarter-century school leadership relationship

Published: March 26, 2024

Gladstone School District Superintendent Bob Stewart reads a story to kindergarteners last week in the Gladstone Center for Children and Families, one of Stewart's signature accomplishments in his 25 years at the top. (Photo by Jake Arnold, OSBA)

Hiring a superintendent is a school board's most important act. Former Gladstone School Board Chair Pete Frohnert and his colleagues invested long hours before choosing Bob Stewart.

"It looks like we picked the right one," Frohnert said.

But now, a full 25 years later, Gladstone is going to have to do it over again.

Stewart, one of Oregon's longest serving superintendents, is retiring at the end of the school year. His long tenure and many accomplishments testify to the relationships he built with his boards over the years, say board members and fellow superintendents.

Current Chair Tracey Oberg Grant, who has been on the board since 2017, has given Stewart grief for making her the one who must finally find his replacement.

Grant said that before she ran for the school board she hadn't realized the importance and reach of Stewart's community connections and knowledge.

"He brings in good people who help the district, but he doesn't take credit for any of it," she said.

Stewart has provided a template for what board members should seek in their next superintendent, Grant said.

"We want someone who will uphold dear traditions but also bring in fresh ideas," she said. "We want to keep this stability intact. We don't want to do it again in three or four years."

By Stewart's count, he has served with 33 school board members since taking the job in 1999. He said the key to dealing with those transitions is understanding the school board is his boss and to always listen intently to its members.

"I have not worked for a board member I have not learned something from," he said.

He attributes some of the recent cultural divide to people not listening to each other.

"People want their voices heard, and when they don't feel like they have an opportunity to be heard, they are going to get louder," he said.

Stewart said school board members' criticisms are an opportunity for self-reflection.

But after it gets tense, he said, "it helps to have a short memory for your emotions and feelings."

Frohnert said it was his job to bring individual school board members around to the group approach if there were disagreements. He said he never felt the relationship with Stewart was adversarial.

"He had visions, but he didn't have an agenda," Frohnert said.

Trained as an elementary physical education teacher, Stewart started in Molalla in 1975 running community education programs. Gladstone hired him five years later, and he rose through the administrative ranks.

Stewart became a superintendent without ever being a classroom teacher. He says his pathway, especially his early work with community education, has given him a different viewpoint.

"A school district is broader than the walls of the school," he said.

Stewart sought out diverse district partnerships, particularly in health care. The Gladstone Center for Children and Families is one of his legacy achievements. The community health care and early learning center would not have been possible without the relationships he built with the school board and the community.

In 2004, Stewart saw an opportunity to buy a grocery store building with several smaller tenant stores next door to the high school stadium. With the building sitting practically across the street from the high school, Stewart was worried about what it might become.

Stewart had his work cut out for him persuading the school board to buy the building during a difficult economic time.

"When he came to me and said, 'I want to buy that grocery store and create this vision I have,' I looked at him and said, 'You really have lost your mind,'" Frohnert said.

Stewart had gained the school board's trust, though, and he had answers for their questions. The district bought the building and launched extensive community engagement led by Stewart to figure out exactly what to do with it.

The Gladstone Center for Children and Families opened in 2009 and has evolved as the community's needs have changed. In addition to the district's kindergarten classes, the center hosts partners that run a county wellness center, a pediatric dentistry clinic, preschool options, community college learning and counseling services among other things.

"Longevity has given me opportunities to do things a new superintendent couldn't do," Stewart said.

The Coalition of Oregon School Administrators does not keep official records, but only a handful of current superintendents even come close to Stewart's long run.

Jack Henderson, who became the Dufur School District superintendent in 1996, appears to be the only superintendent who has served longer in one district. His experience agrees with Stewart's. He said leaders who immerse themselves in the community can build the trust to really make things happen. He counts passing two bonds in the past 15 years and developing two significant endowment funds as a reflection of the trust he has built.

COSA Deputy Executive Director Krista Parent said Stewart has been "the rock" among Oregon administrators.

"He has done incredible things and influenced leadership across the state," said Parent, who will become executive director in July.

She credited him with being at the forefront of school districts' offering wraparound services with the Gladstone center. Parent said that kind of forward thinking is a direct result of having a good co-governance relationship with his school board.

A solid school board-superintendent relationship makes for a steady district, Parent said, and any change in superintendent, even from a good leader to another good leader, can be hard on staff and students.

"Keeping leaders in one place is good for the system and good for kids," she said.

Stewart said he had opportunities to leave Gladstone but never applied for one. Stewart credited the school board with "walking alongside" and supporting him, allowing him to do interesting work.

"Superintendents need to be able to tell a story of here's where we are, here's where we need to be, and here's how we get there," he said. "The board needs to be brought along with the story, and they need to be able to interject the part of the story they think is important."

- Jake Arnold, OSBA
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