News and Opinion from Sisters, Oregon

Dempsey announces retirement

Dennis Dempsey will retire at the end of this school year.

The High Desert Education Service District's long-time superintendent has served in education for more than 36 years, including his stint as the modern Sisters High School's first principal from 1992 to 1999.

Dempsey had been working in Homer, Alaska, when his old friend, Sisters band instructor Dennis Lindhal, encouraged him to apply for the top job at the brand-new Sisters High School.

"I came down in February 1992 for a week and hired everybody, then I came down in July and started working," Dempsey recalled.

Dempsey has also served twice as an interim superintendent in Sisters and remains intimately connected to his hometown district.

"When you are an ESD superintendent you get to wear many different hats depending on the needs of your local school districts," said Dempsey. 

As superintendent for the High Desert ESD since 2000, Dempsey has worked to provide cost-efficient, regional services to several of Central Oregon's school districts, including Bend-La Pine, Sisters, Crook County and Redmond.

The lifelong educator sees serious challenges - and opportunities - in the field in the coming years. Scarce school funding dollars combined with revolutionary changes in classroom technology set the stage for some potentially radical changes in how education is delivered.

"Technology is going to play a bigger role in kids' educational opportunities," Dempsey said. "Looking forward over the next five or 10 years, we're going to be flat-funded or (there will be) less money in education...We're going to have to do business a lot differently."

In the classroom, that means more effective use of technology like the iPad, enabling students to work in hybrid environments - partly in the classroom and partly online. Dempsey believes schools will be able to match students with subject-area specialists in new ways through online teaching.

"You tie the teachers' strengths to the kids' needs," he said.

Dempsey also believes school districts will have to change the way they operate - starting with reducing the number of districts in Oregon (currently 198).

"Do we really need 198 school districts? No," he said.

In his time with the ESD, Dempsey has focused his career on ensuring that all school districts - regardless of size - have access to quality special education, information technology, financial and administrative support services that are affordable and allow teachers to focus on classroom instruction.

"A lot of things can be done on a regional basis," he said. "Every district doesn't need a business manager, an HR supervisor - go down the list of things."

Dempsey said he recognizes that change is difficult, but "if we don't start having these tough discussions, the whole system is going to implode... All of us have to face the reality at hand... it's about bringing everybody along so that they understand why we have to do business differently. Top-down stuff isn't going to work. You sit down with people and say: 'This is where we are; this is where we've got to go - what are we going to do?' You've got to engage people at the ground level."

Transition planning is underway to prepare for Dempsey's departure from the ESD in June. For his part, Dempsey plans an active retirement. He will continue to serve on the St. Charles Medical Center Board of Directors and will continue to teach for and oversee the University of Oregon's programs in Central Oregon for educators seeking administrative credentials.

He plans to travel some, and enjoy his grandchildren, who live in Central Oregon.

"Everybody tells me retirement is great," he said. "I just want to find out - but not find out completely."

Author Bio

Jim Cornelius, Editor in Chief

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Jim Cornelius is editor in chief of The Nugget and author of “Warriors of the Wildlands: True Tales of the Frontier Partisans.” A history buff, he explores frontier history across three centuries and several continents on his podcast, The Frontier Partisans. For more information visit www.frontierpartisans.com.

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