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Over the past two years I have talked to only a handful of administrators.
This is because there really aren’t that many of them compared to the number of taxpayers, parents, or even educators.
Some that I have talked to in that time aren’t in the same positions now, even though they have remained part of the district.
What I present here is an observation both of these few administrators and of the administrative system as a whole.
Disclaimer: These are my impressions, not statements of fact.
I will be presenting the most common and most vocal views I encountered.
None of these come from a single person and I will use no quotes.
What counts as an administrator?
For this article the “administration” only means: the superintendent, the treasurer, the principals, the department managers, and any supervisors in charge of district functions.
The term “administration” is a little vague so let me be more precise about what I am talking about.
The positions are strictly structured, each position has people above them and below them in a chain of command.
I don’t count the members of the board of education as administrators.
The board as an entity does oversee the administration but individual board members do not.
The thing all administrators have in common is that they live chaotic lives so others can live in a reliable system that is safe and predictable.
Every emergency is brought to them.
Even when there is no emergency something is always about to go wrong and administrators are the ones that are expected to prevent it.
The Current Situation: Out of Pandemic, Into Uncertainty
There are always problems the administration is dealing with.
But it seems that the problems that cause the most anxiety for it are the ones it can’t directly control.
While working hard to heal after covid the administration is left guessing at how to best weather a looming school funding storm.
Federal and State funding changes are causing those anxieties now.
At the Federal level the department of education is in limbo.
Before that it was covid.
Covid’s impact still echoes, mostly in the form of connections lost to the isolation of lockdowns.
Meanwhile, school funding looms in the future but constantly changes.
Federal funding is almost always earmarked for specific programs but those programs are often critical things like lunch discounts.
At the State level, property taxes have come to a head and frustrations have become powerful.
These outside forces may totally reshape 2/3rds of our district’s funding with no solid indication of how things might change.
The Administration’s Relationship with the Educators: Working Trust
The relationship between administrators and educators is somewhat strange because the educators are subordinates in the administrative system.
Also, because the relationship is governed by state law, union rules, and district policy it can feel unnatural.
This is particularly odd for some because it is common for educators to become administrators.
It is very rare for an administrator to return to being only an educator but there is some transfer between these groups.
Something that strains the relationship with educators is the need to allocate limited resources and avoid favoritism.
The higher in the chain of command administrators get, the fewer easy and correct answers there are.
So the administrators are left having to choose who will be satisfied, who will remain unsatisfied, and hope that everyone will be able to live with the outcome.
In short, administrators have to keep a team working together.
Administrators need frank honesty and understanding trust from educators.
Because of the regulated chain of command it can be difficult for administrators to receive needed feedback from educators.
The administrators I talked to tried to work towards personal and honest relationships.
What I mean by that is the administrators are looking for respectful but frankly honest feedback from educators.
Honest reports, honest critique, and even honest disagreements are all needed so that administrators can do their jobs well.
This feedback can take the form of internal anonymous surveys.
But it can also be something as simple as a casual private conversation at the coffee maker.
Both of these remove the social and chain of command pressures that can’t be avoided at staff meetings.
In return the administrators seemed to hope for an understanding trust.
Trust that the decisions administrators make are needed, deliberate, and for the best good of the students.
When an administrative position in filled by a new person they must work to grow a new relationship with established educators.
Recent events have shuffled a lot of the principal level administrative staff around the district.
When this happens these personal relationships with educators have to be renegotiated and regrown.
As I understand it, no fewer than 9 administrators were moved, hired, or promoted to fill vacancies this last school year cycle.
Most of the new administrators were already filling roles in our district, so most of these are familiar faces for educators.
Still, serving with new administrators disrupts the working relationship and settling back in takes some time.A Full List of Changes This Last School Year Cycle
Left District / Retired:
High School Head Principal.
Head Athletic Director.
Communications Coordinator.
Secondary Curriculum and Gifted Coordinator.
Transportation Supervisor.
Wooster High School:
New Head Principal was previously Associate Principal.
New Associate Principal was previously Parkview Principal.
Cornerstone:
New Principal was previously Keen Principal.
New Administrative Intern was previously Cornerstone Teacher.
Parkview:
New Principal was previously Cornerstone Administrative Intern.
Keen:
New Principal was pervious Wooster student from Utah.
Athletics:
New Director is from Marysville.
Communications:
New Coordinator was previously District Secretary
Secondary and Gifted:
Coordinator position not currently filled.
Transportation and Safety:
Supervisor was previously Cornerstone Principal.
The relationship between administrators and educators will always be a professional working relationship.
But as administrators build their reputations, comfort and trust can slowly set in.
The administrators I talked to were mindful about the need to keep that relationship growing.
The Administration’s Relationship with the Parents: Inviting Connection
The main thing the administrators wanted from the parents was involvement and reconnection with the schools.
Covid and the lockdowns broke old habits that kept parents connected with the administration and lingering isolation have been hard to overcome.
Covid was a major shock to the relationship between the administration and the parents.
Some of it was caused by the policy whiplash of going into and then coming out of lockdowns.
As an example, attendance policy went from a hard focus on doctor’s notes to banning children from school for weeks of isolation if they had possible symptoms and then right back to doctor’s notes and attendance warnings.The policy whiplash was a shock but the school closures and remote learning have cast a long shadow over this relationship.
From children to adults, the isolation of lockdowns has changed habits.
In particular, in person connections that used to be regular are now difficult to organize and sometimes poorly attended.
That is slowly starting to change.
Partly that is because administrators have led the system in a constant effort to reconnect with parents.
New systems like the Parent Square app are helping the administration connect with parents all in one place.
The most recent move by the district that speaks volumes to me on how much work it has put into reconnecting is the new Parent Square app.
This app is new this school year and not fully up to speed yet.It is expected to eventually replace several different ways to keep in communication with parents.
When fully up to speed Parent Square be able to replace all these functions:
The mass phone call/texting system.
The mass email system.
The Remind teacher communication system.
In-person document signing systems.
Targeted community newsletters.
Other functions by letting parents move school events directly to their phone calendar from the app.This is remarkable to me because school systems do not change like this easily.
It can be done but the amount of work that goes into it makes it rare.
That indicates to me just how much energy the administration has put into inviting parental connections.
I saw a lot of small, personal, efforts to revive old connection points or create new ones.
Administrators at the principal levels that I have talked to say that regular small events are inviting families back into the schools.
These events started with the children in mind but encourage parent connection.
For example, an event at Edgewood invited parents to come and play math games with their students.
This let the students teach parents the number practice games they had learned in school.
But it also welcomed parents to connect with the building and the staff.
It was remarkable to see so much time and energy being poured into this relationship.
I also think this has been a group effort and it seemed to be greatly supported by the educators.
It is probably second only to the time and energy being poured into the students.
The Administration’s Relationship with the Community: Confused Service
This relationship is the strangest one I have encountered because it includes a member that isn’t even human: the district itself.
What do I mean by that?
Taxpayers treat the district like it was a living person completely independent of who the administrators are at the time.
I suspect this is because taxes remain impactful over decades and school buildings being built or closed reshapes the community for generations.
So, we see the district as a living thing that helps or harms us.
This is something administrators have to deal with when they interact with the taxpaying community in particular.
This is a long story best told from the district’s point of view.
The short version is when the levy failed in spring 2023 it shook what the district thought it knew about community support of a plan it had worked on for about 5 years.
It is finding out that it has trouble reaching out to the community for communications and feedback.
It is not yet sure what the community wants next but it keeps trying new things to find out and is quietly signaling willingness to change.
Since we hold the administrators to the history of the district I think it is appropriate that I talk about this relationship from the district’s point of view.
When I say this I mean that I am reporting on the district as a living machine, like we taxpayers treat it, not on any individual administrators.There are several elephants in the room when it comes to the relationship between the district and the community.
I want to tell the story of one of them from the district’s point of view.
Keep in mind, this means I am not talking about any person.I believe the district thought it was being a good public servant until spring 2023.
It had saved up money so it wouldn’t have to bother voters with operations levies for as far out as it could see.
It had gingerly navigated covid as best it could.
It knew work needed to be done on the school buildings.
It had worked for years on a plan to keep only the best buildings and build great new educational homes for the community’s children.
Then, when it came time for voter approval, only 22% supported the plan at the ballot box.I think this was really very shocking to the district.
It thought it had done everything right.
It had consulted with a committee of dozens of community members for years.
It had applied for extra money from the State.
It wasn’t going to touch the savings it had accumulated so the community would still be spared an operations levy for as far out as it could see.
But the community had yelled “No.”
Why?To the district’s credit, it did not stubbornly try the same plan again.
It realized that something had gone very wrong and has been trying to figure out exactly what ever since.
In spring 2025 it asked if the problem was the price by offering a smaller levy.
Voter approval jumped from 22% to 42% but the answer was still a very solid “No.”
Again, it has not been stubborn and instead has been trying to figure out where to go from there.The district does seem to realize that it has lost touch with the community somewhere along the line.
It isn’t certain when that happened exactly.
It thought it knew what the community wanted but 2023 showed it didn’t.
A lot of what it has done since then is desperately trying to listen.
It has found that it isn’t sure how to reliably listen or talk to the community anymore.
It did a community survey after spring 2023 and that helped clarify some things.
But when it reaches out more generally to the community it finds that the local paper isn’t local enough, social media isn’t concentrated enough, and meetings are not well attended.
That is the district’s perspective as far as I can read it.
No current administrator was responsible for this.
The superintendent, the treasurer, the entire school board, and most of the principals are all different.
None of them had anything to do with the beginnings of the 2023 levy plan.
And yet the community will hold that misjudgment of taxpayer desire against the district as if it were someone that has wronged them.
This is the main driver of the relationship with the taxpayers.
The administrators, the people serving now, are doing their best to guide the district through its past mistakes.
I saw them trying to reconnect with the community, each in their own way.
I saw them spending any extra energy they have to try to fix it.
However, it was also my impression that this is not their first priority.
They seem to be focused on the children and the parents first.
But I did feel the administration understood that the disconnect is there and needs real work from their end.
Author notes:
My opinion on the situation:
The administration relationship with the educators will be disrupted by recent changes but will likely grow into good working relationships going forward.
The administration relationship with the parents shows a lot of promise and is the primary focus of new engagement.
The administration relationship with the taxpayers was broken in 2023 but efforts are being made to slowly heal old wounds.
[This article was originally published September 26th, 2025]
This is only one side of the public school situation in Wooster.
This has been a lengthy 4 part series and I thank anyone who has stuck around for the entire thing.
Political Statement:
As I am now a candidate for the Wooster city school board this article blurs the line between what is campaign material and what is community report.
So, because I have paid my time into it and because it may sway opinions for the election I now state:
Paid for by Why the Hill not
This is my election committee name.
Though this might be considered a campaign post, my personal hope is that this article helps bridge understanding in the community.
That has been the goal of this 4 month project all along.
Wooster Interpreter 
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