As far as Dean Hess is concerned, a decision to join the Oconto Falls School District as its superintendent a decade ago has paid off for his family and the district.
Hess will retire at the end of the 2024-25 school year after a 31-year career in education that also included stops in Plainfield and Wausau.
He will spend much of his time leading up to his retirement helping the district transition to its new superintendent, current Oconto Falls High School principal Stuart Russ.
Hess, originally from Elcho, came to Oconto Falls after 17 years as an assistant principal and principal at two middle schools in Wausau.
“You are trying to find a good fit,” he said. “More than anything, I felt that Oconto Falls was a good fit for my wife and me. I had done the schooling and was taking a look at some different options. When I came here to Oconto Falls, the first thing that caught my attention was all the really positive things that were happening in the district.”
Hess checked out the district’s website leading up to the interview process in 2015.
“You can learn a lot if you go on the website of a district,” he said. “It was very quickly apparent that it was a successful school district with a lot of support from parents and the community and a very solid board of education. When I came here, a majority of the board had been in place for 10 years or more, and they were very focused on the needs of kids, which isn’t always the case. We did a tour of the district, and one of the first things I noticed is the upkeep of the facilities. That says a lot for the communities that make up this school district, because they have to be willing to support that to have that level of opportunities for kids.”
One of Hess’ first stops was the high school’s performing arts center.
“I remember walking in and just thinking, ‘Wow, it’s really neat the way the community supports the arts,’” he said. “That is a team situation. You have phenomenal instructors that are inspiring the kids, and the kids are doing a ton of work to perform. To have that support from the community makes it all an opportunity that’s there. I had a chance to interact with staff members and students as part of the process of coming here and that just kind of solidified that it was a good fit.”
A decade later, the district is preparing to open a new middle school for grades 6-8 across the street from the high school. The school is scheduled to open in time for the start of the 2025-26 school year and will replace the aging Washington Middle School on South Washington Street.
“Nothing happens without teamwork and the teamwork in this community is amazing,” Hess said. “In my interview, they gave me the opportunity to ask questions, and one of the questions I had was what are going to be your expectations of me. They told me one of the things we realize is that our middle school is aging, and we’re going to need to figure out a plan to either refurbish the middle school or replace it. They told me that early on. As I was out in the community in that first couple of years, it was evident that the community members were in a similar mindset. They recognized that there were serious challenges with Washington Middle School’s structure.”
The original building dates back more than 100 years and had several updates over the years.
“There were additions to the original part of the building multiple times,” Hess said. “You don’t know for sure until you run a referendum, but there were people that were reaching out and sharing their support for addressing that.”
Besides dealing with an aging school building, the district had other concerns, according to Hess.
“One of the first things that needed to be addressed when I came is we were in a tough financial situation,” he said. “There are multiple ways of looking at that. Dave Polashek, the previous superintendent, and the board worked together to be very frugal with taxpayer dollars, and they did the best they could. Funding for public education is a difficult scenario, because it drastically relies today on operational referendums from the public.
“We started working through our budget and our finances and recognized that if we didn’t do an operational referendum, we were going to need to lay off members of the team. We didn’t have time to do that in my first year, and we laid off nine people. We let the public know in the second year that if we didn’t pass an operational referendum, those cuts would be even deeper. Folks wanted to try to maintain the high level of education that they have here, so they supported that referendum. One of the things I shared with the public is unless public school funding changes, we would have to come back to them at some point in the future. Unfortunately, it didn’t change, and we did have to go back to them.”
Voters later turned down a referendum to build a new middle school.
“Interest rates were very favorable at that time, so the planning team was trying to determine a reasonable ask of the community,” Hess said. “The good news was our school district had a significant amount of debt that was dropping off at the same time we were looking to potentially pass that capital referendum. We were very up front with people. If the community chose to pass the referendum, essentially the mill rate would stay similar, but if you don’t pass it, your mill rate will go down.”
A district survey indicated support for a new school, but the referendum failed.
“We were looking to not just do the middle school, but also do other work throughout the district,” Hess said. “On a second survey, people said, ‘You know what? We support a middle school, and we support the safety initiatives, but let’s keep it at that level.’ That’s what we did. We went back and said, ‘Listen, we’re looking for a middle school, we’re looking for secure entrances on all our buildings and we’re looking for some roof work.’ The support of those folks is what you now see across the road. We have secure entrances in our three schools minus Washington.”
The district’s other schools are Oconto Falls Elementary School near the high school on Farm Road and Abrams Elementary School in Abrams.
“Both those elementaries will remain open,” Hess said. “They’re both very well attended. If at some point down the road, we see growth that is beyond what the two elementaries can handle, there’s an ability to put a wing on the new middle school and bring fifth grade up to that building if we had to.”
Like many northern Wisconsin school districts, the Oconto Falls district includes a large geographic area.
“Our school district is made up of 10 different municipalities,” Hess said. “We have all these townships north toward Kelly Lake and we go all the way to Brown Road (the county line between Oconto and Brown counties). I think it says a lot about the communities we serve. They value public education. If they didn’t feel passionate about that, I’d say we would probably not be building a new middle school.”
Hess said he is impressed with the support the district’s schools and programs receive from the community.
“You come to a track meet or go to a baseball or softball game or concert, they’re incredibly well attended,” he said. “People enjoy watching their kids, their grandkids, their neighbors’ grandkids in these different activities. It’s something that brings joy to them and it brings joy to the kids when we support what they’re doing. Our programs are consistently improving, and that says a lot about the coaching staff and kids. They’re putting in the time and effort and constantly trying to improve.”
Hess also led the district through the COVID-19 pandemic, which began in 2020.
“We didn’t necessarily know it at the time - 2017, ’18, ’ 19 - but we really started recognizing the need for upgrades of technology infrastructure,” he said. “We did that and when we got into the pandemic, our staff had had the professional development to go virtual. A lot of districts struggled with that, but we transitioned quickly, because our staff had the capability. The only reason we were able to do that is because those operational referendums were passed, which allowed us to do the professional development. The staff was willing to do that beyond the normal jobs. When we hit the pandemic, we were able to adapt quickly. Obviously, no one wants to relive the pandemic, it’s nice to know you were proactive and not reactive.”
An investment in staff has paid off for the district, Hess said.
“Because money had been so tight when I came here, professional development basically had a moratorium, because there hadn’t been any funding,” he said. “When we were able to get an operational referendum passed, we were able to reinvest into our staff. When you ask people in public education why they left, quite often the reason is they didn’t feel valued and didn’t feel like they were growing professionally.
“We take that to heart and offer people significant opportunities, whether it’s national board certification, summer institute classes,” he said. “In a lot of cases, they have input in helping decide what’s going to happen. That doesn’t happen without community support, and that trickles down to student learning. If your staff is improving at what they do, you’re better able to meet the needs of the kids.”
Hess believes he’s leaving the district in good shape.
“We still today - 10 years later - have a very strong board of education,” he said. “We’ve had new board members come on, but they’re very focused on students and what they feel is in the best interest of the kids. I strive to guide people to be thankful for our board members. Being a board member is very difficult. Every time you make a decision, usually, somebody’s not happy with it. With social media today, it can get divisive. I feel we have a strong board and I don’t take that for granted.”
The community continues to support the district, which has a staff of about 300 and 1,700 students, Hess said.
“When you come to activities here, people are willing to step in and coach,” he said. “In order to have all of the co-curriculars and extra-curriculars, you have to have advisers and coaches. Our staff is unable to do it all, so when you come to our activities, you’ll see staff members, parents and community members in those roles. That doesn’t happen everywhere, because that’s a big investment of time and energy.”
Students and staff play a key role in the district’s success, according to Hess.
“When I look at other places, they’re dealing with situations we don’t have to deal with,” he said. “For the most part, our kids make good choices, they look out for each other, they take care of each other. When kids have different needs, those kids would get picked on in other places. We still have some of that, but it’s less than other places. I’ve also seen kids policing some of that on their own, which is pretty impressive. When I look at what it takes to be a successful teacher today, it’s a tough job. They’re willing to come in, do the job every day, do professional development to get better.”
Hess is originally from Elcho, a small community between Antigo and Rhinelander.
He enrolled at the University of Wisconsin-Stevens Point after graduating from Elcho High School.
“I didn’t know what I wanted to do,” he said. “Both of my brothers are engineers. I started out in an engineering program - paper sciences - at UW-Stevens Point. I did that for about a year and a half. I did an engineering internship at Wisconsin Tissue Mills in Neenah and figured out that wasn’t what I wanted to do. I really enjoyed science classes and went back to Stevens Point to enroll in education. Once I made the decision, I was off and running. They assisted me in that transition from engineering to education.”
One of Hess’ first experiences after changing his major included teaching a chemistry class at Pacelli High School in Stevens Point.
“The teacher was amazing, and it was just the opposite of my experience at the paper mill,” he said. “I loved it and I knew this is what I want to do.”
After graduating, Hess taught middle school science in the Tri-County School District in Plainfield for four years before being named assistant principal at Horace Mann Middle School in Wausau, where he spent seven years. He left that job to be principal at John Muir Middle School in Wausau, a position he held for 10 years until coming to Oconto Falls.
Hess also served in the Wisconsin Army National Guard, where he was a platoon leader, company commander. That military experience helped him make decisions as a school superintendent.
“The military teaches a lot of leadership as you progress through the ranks,” he said. “I did 20 years with them, deployed multiple times and took a task force over to Iraq.”
Hess thinks of himself as a hands-on superintendent.
“I go to events, but you can’t go to all of them and that’s one of the things I struggled with,” he said. “You want to be there for all the kids. On any Tuesday, Thursday or Friday night, there are three or four events going on. You have to pick and choose, but the kids appreciate it when they see you there. The kids need to know who you are.”
Hess has played guitar for elementary students and even helped out in a bus driver shortage.
“We started having serious problems with our bus numbers for drivers,” he said. “We literally were starting to have situations where we didn’t have anybody to drive a bus after school for middle school volleyball. I thought, ‘Well, I have a background where I’ve driven lots of things. I was in the military and I was driving tanks and helicopters. I can drive a bus.’ I got my CDL and started helping out. One day, I opened the door, a kid jumped on and said, ‘How come you’re driving the bus?’ I said, ‘They needed someone today.’”
Hess said he will miss interacting with staff and students.
“I won’t miss the stress level,” he said. “I definitely do it to myself. I want things to be as good as they can possibly be, because a second-grader only gets one opportunity to be a second-grader. If you don’t do your best job, they lose out.”
Besides wrapping up his 10th and final school year in Oconto Falls, Hess is also helping with the transition of Russ to his new position.
“He’s going to do a great job,” he said. “He’s currently the high school principal and he’s been doing a great job in that role. I’m already working with the board president and Stuart on a transition plan.”
His contract runs through June 30.
“June and July are extremely busy months,” he said. “You’re wrapping up all the pieces from the last school year, you’re doing all the professional development of staff for the new school year, and you’re also in the process of hiring new folks.”
Hess is unsure about his long-term plans, but said he plans to remain in the area.
“When I think about what comes next, I’m looking forward to investing more time with my family,” he said. “My wife and I live in Stiles. We love the area, and we’re planning to stick around. When I started thinking about this process, a friend of mine gave me what I thought was some really good advice. He said, ‘Make sure that you have something you’re retiring to and not just retiring from.’”
Hess doesn’t know what that “something” is, but said he’ll eventually come up with a plan.
“I anticipate that I will have a different job working in some capacity,” he said. “Part of me thinks that it would be really neat to coach or advise people that are in leadership positions. I don’t know exactly what this will look like yet. Will it be advising future teachers? I don’t know yet, but I’m sure it’ll be something, because I will need to have an active life. That’s what I enjoy.”
Although his career as an educator and administrator is coming to an end, Hess said he wouldn’t change a thing.
“Education has been fantastic,” he said. “If we do a good job of educating kids and giving them different experiences, it makes them better adults. They can then choose what they want to do. Do they want to go into the trades? Do they want to go into the military? Do they want to go to college?
“If we don’t do a good job, it’s just the opposite. We’ve hindered kids. We do a nice job of setting kids up for success. We give them a lot of different opportunities, not just in math, science reading, history and English. It’s neat to see how all of our departments and grade levels work together to try to create opportunities for kids to make informed choices.”
Hess said he had a good feeling after interviewing for the job a decade ago.
“When I came here, I literally walked out of the interview and said to my wife, ‘I think this would be a good fit,’” he said. “I hope they feel the same.”


