Meeting in the Middle
How to keep your district’s relationship with your teachers union low on conflict and high on cooperation

Between 2007 and 2023, there were 772 teacher strikes, affecting over 11.5 million students. In a 2024 article published by The Economist, the Chicago Teachers Union is described as “a model for radical left-wing organizing.” Some parents are even beginning to cite district unionizing as a reason to opt out of public school altogether, accusing unions of protecting “bad actors.” And yet, the research is clear: Positive district-union partnerships lead to improved student outcomes.
With headlines like “48 Million Student Days Lost,” it’s easy to think of teachers unions as the enemy. However, unions have the potential to be a positive partner in every school district’s most crucial work of supporting students—because supporting students means supporting educators. “Our district supports our building principals, who support our educators, who support our students,” says Clover Park School District’s Ron Banner, Washington’s 2025 Superintendent of the Year. “Unions form a bridge in that linear support system. People need to know that they have an advocate.”
And Dr. Charles Heckscher agrees. Heckscher is the co-director of the Public School Collaborative, which is housed under Rutgers University’s School of Management and Labor Relations. “Management networks tend to be top-down in their bureaucratic structure, but unions cross that within schools. They foster conversation across the whole school system,” he says. “And as you increase the strength of those partnerships, student performance improves.” Heckscher goes on to admit, though, that “the ideology of politics can get in the way. Each political party has ideas about what needs to get done in education, and that can kill collaboration at the local level.”
In other words, collaborating with your local union is both important and difficult. That’s why we’ve consulted the experts. In addition to Heckscher and Banner, we spoke with Damen Cooper, interim superintendent of Montclair Public Schools—a New Jersey district that has participated in workshops facilitated by the Public School Collaborative. Here, we’ve synthesized their advice into actionable strategies for collaborating effectively with local unions.
It’s not personal; it’s personal.
Before we dive in, let’s further unpack exactly why relationships between districts and their local unions can be so tough to build and maintain. While it’s true that the narrative around unions is increasingly fraught, that’s not the only element at play here. So what exactly makes union-district relationships so difficult?
Often, when we talk about building relationships, we’re talking about a distinctly interpersonal skill set that allows one person to connect with another. The relationship between a district and their union, though, goes beyond person to person; it’s a relationship between organizations. “This work is personal in that you’re the one doing it,” Cooper says, “but it’s not personally targeted at you—it’s targeted at the position you hold. But when the fire gets hot and the questions are flying at you, it’s hard to keep that perspective. You automatically begin to take things personally.”
Regardless of which organization you represent, district-union relationships require the emotional distance necessary to honor organizational processes, as well as the passion and connection needed to advocate for the people and issues that matter to you. It’s a fine line to walk. Let’s take a look at how you can keep your balance.
Collaborative Conversation
“Management generally sets the tone and unions respond to it,” Heckscher says. “If they’re brought in collaboratively, they tend to respond collaboratively. If you exclude them, then they’ll fight.” Knowing how to communicate effectively and participate in hard conversations is crucial for district-union collaboration. Here’s how to set the right tone.
Come to listen—not to win the argument.
Early in Banner’s career, when he was an assistant principal, he encountered an incident involving a teacher who didn’t follow district protocol after a student incurred an injury. Banner reminded the teacher of the district’s expectations, “and she kind of blew up at me over email,” he says. “I had to have a conversation with that teacher and the principal because it was almost getting to a place of insubordination.” Banner collected a stack of documentation and evidence to bring to the meeting with him, but a leadership coach the district was working with at the time stopped him.
“She said, ‘What is all that?’ And I said, ‘This is my evidence!’” Banner tells us. “And she just looked at me and said, ‘Ron, I can’t tell you not to bring that, but if your goal is to win this argument, we’re never going to figure out what’s going on.’” And the leadership coach turned out to be right; there were interpersonal circumstances at play that extended beyond the incident in question. Only once the team unpacked those foundational fault lines were they able to move the conversation forward.
“So coming back to our union, it’s not about going into a conversation to be correct,” Banner explains. “It’s about listening, seeking first to understand. Then we can have a conversation from there.”
Instead of fighting, get good at disagreeing.
“I don’t like fighting, but I have no problem with disagreeing,” Banner says. “You have a perspective. I have a perspective. I’m typically trying to convince you that my perspective is the right one or vice versa—as opposed to fighting, when people are taking shots at each other.”
Think of it this way: If everyone had the same perspective, collaboration would be pointless. Diversity of ideas is how we generate strong solutions, but only if we learn to disagree effectively. “It’s about respect,” Banner continues. “It’s a willingness to hear something that’s not so flattering about your organization and still respond or rebut constructively. That’s the beauty of this work. The union has their take, I have my take, and we should be able to talk about it.”
At the same time, Banner is quick to clarify that “we’re all humans. We all have emotions. Something might trigger us in a certain way.” In that case, he suggests giving yourself time to process and regulate your emotions so that you can go into conversations with a cool head.
Recognize the ever-present potential for collaboration.
“One thing we learned while going through training with the Public School Collaborative is that you can think of decision-making as a pendulum,” says Cooper. At one end of the pendulum are the decisions that superintendents can make unilaterally, such as funding a teacher celebration night. At the other end of the pendulum, however, are the decisions that are impossible for superintendents to make without union input. In the middle are the decisions that belong to the superintendent but are best made with input.
“What you really find out if you engage in conversation is that most decisions that a superintendent makes can be made collaboratively,” Cooper says. “And when you offer that kind of collaborative ownership, you have union buy-in—and that’s where you begin to move the needle.” If you want to set a positive tone with your union, what would it look like to consult them even when you don’t have to? Building the foundation of collaboration when the stakes are low will help build the kind of trust you’ll need as the stakes get higher.
Combat polarization by centering shared goals.
“Schools have a leg up on other unions because they are able to center their work around a common goal: students,” Heckscher tells SchoolCEO. “There’s this sort of uniting emotion that is less prevalent in other industries. Most people in steel don’t really care about steel, but everybody cares about kids.”
“And unfortunately, we’re in a polarized society right now with the political left and right,” Banner adds. “The question is: Can we meet somewhere in the middle? Because more often than not, we have more shared goals than differences. My hope for any conversation is that we can come to the middle and figure out what we have in common.”
Don’t be afraid to seek external support.
In addition to conducting original research, the Public School Collaborative facilitates collaboration workshops with districts across New Jersey. Having worked with the Public School Collaborative, Cooper understands well the impact of soliciting the support of a third-party mediator. “Both sides have a vested interest, and sometimes you’re just too close to the work,” he says. “It’s helpful to have someone on the outside who can be the voice of reason, who can hear both sides and keep the conversation going in a productive manner.”
And while you may not be in New Jersey, maybe there’s collaboration-focused professional development available in your area or online. If not, what would it look like to connect and learn from nearby districts who have had collective bargaining success? Plus, if you need them, there are always mediation services accessible at both the state and national level.
Collaborative Processes
Like we said earlier, district-union relationships go beyond person-to-person connection; they’re relationships between organizations. That means it’s crucial to have collaborative decision-making processes that are sustainable into perpetuity. Could you schedule regular meetings, even—and especially—when there are no problems to solve? Agree on an action sequence for who does what when an issue arises? Build a structure for efficient communication in different circumstances to ensure stakeholders are notified quickly and effectively?
The truth is: The processes you’ll need most depend on your unique circumstances. There’s no magic strategy that will work in every instance, and we don’t want to waste your time by getting too in the weeds with irrelevant approaches. Instead, let’s take a look at some high-level guidance for why processes matter and what you’ll want to keep in mind as you consider yours.
Seek to understand the history behind existing processes.
We don’t need to tell you that superintendent turnover is a growing concern. And as you know, whenever a new superintendent moves into a district, they inherit the relationships—positive or negative—cultivated by their predecessor. The relationship between a district and its union is one of the relationships a new leader must adopt, and that goes both ways. New union leaders and new superintendents must learn to work within already established processes.
“So when a new superintendent comes in and their association immediately starts asking for something, that new superintendent may get defensive because they don’t know the history,” Cooper says. “So then the superintendent might say, ‘Here’s what we need from the teachers association’—who might turn around and say, ‘Whoa, whoa, whoa! We’ve already tried that. Slow down.’”
It would be unreasonable to expect a new leader to get caught up on years, if not decades, of history immediately. Instead, remember in those first conversations that you may not yet have all the necessary context for why decisions are being made in a certain way. Commit yourself to asking questions and learning as much as you can about the processes already in place. Making change will be easier if you operate within the already established system rather than expecting to dismantle the system completely from the get-go.
Don’t try to overhaul existing processes too quickly.
“You can’t come in and flip the entire pancake over,” Banner tells us. “It’s just too much. You can’t start things over every time somebody new comes in. Same thing with the union presidents. They shouldn’t feel like they have to start from scratch.” Ideally, your processes should be both easily repeatable and transferable so that the district-union relationship can easily accommodate someone new in the leadership seat.
We’re not suggesting that all new leaders need to be exactly like their predecessors; rather, we’re saying leaders shouldn’t be linchpins. The process of decision-making—not the leaders—should be the scaffolding for an effective district-union relationship. As Banner says, “It’s about looking for someone who can step in and fill the shoes, but tie them differently.”
Consider bargaining for union-district leadership meetings.
“When you implement a strong process that has roots and gains traction, the process begins to drive the work. It becomes the culture of what you do,” Cooper tells us. “Then, regardless of who comes in, if they’re not a part of that culture, they’re seen as an outsider.” How, though, can you build the type of process that can be sustained into perpetuity regardless of who is in leadership? For Montclair Public Schools, the answer was, in part, to include regular district-union leadership meetings in their collective bargaining agreement. “That’s how important our board of education and district felt it was to find a way to cement this work,” Cooper explains.
Utilize available resources.
Now, you may be thinking: All this “processes and systems” talk sounds great, and I agree that it’s important—but what if our decision-making process simply isn’t working right now?
If that’s the case, never fear. The National Education Association has abundant resources for free on their website, including a guidebook for district-union collaboration. So if you’re feeling overwhelmed and looking for a place to start, we suggest page 118 of the guidebook, which asks: “What committees or other working groups already exist in our system, and at what levels? How do these existing groups align with our partnership’s identified overarching content goals?” And if that feels overwhelming, then start back up at the first page of the guidebook. It doesn’t matter where you start, only that you do.
Remember: Processes ensure fairness.
Banner tells SchoolCEO that there have been times when the union has argued on the behalf of individuals who he believed had undeniably done wrong. “And so I try to look at the union as defending the process, not the person,” Banner explains, “because there is a chance I got something wrong or one of my administrators could have done something different. Sometimes it’s their job to challenge us.”
Processes are key to ensuring fairness—and this goes beyond the basic process of negotiation. Establishing clear collaborative processes gives everyone a script to follow when decisions are being made and problems are being solved. They remove the chaos of disagreement because no one will be surprised by what happens and when. “The process is just as important if not more important than the product,” Banner says. “There’s no promise to the end result. The promise is that we’re going to touch base, respect each other, listen and hear each other—and then the outcome should be along the lines of our mission and vision.”
Strong Ties, Strong Workforce
For better or worse, union negotiations make headlines—but a good relationship with your union goes beyond the ramifications of a news article. Taking care of students means taking care of teachers. Strengthening your ties to your union is key to elevating your educators, reducing turnover and building your reputation as a district that cares about students and staff alike.
“When you’re working toward a better atmosphere for your teachers, your administrators, your custodial staff, your security guards—everyone who has contact with your kids,” Cooper says, “when you’re working toward a better environment where they feel appreciated, things are going to improve.”