The Power of Listening
September 01, 2026
Building trust when the superintendent opens the school system in ways that are visible and felt
Caitlin Sullivan of Leading Now places conversations with stakeholders as the foundation to building trust. PHOTO COURTESY OF CAITLIN SULLIVANFirst-year superintendents often feel radically exposed to the public eye, especially compared to when they were in prior roles as teachers in closed-door classrooms or assistant superintendents with central-office insulation.
Now, every decision is out there. Every misstep is amplified. For superintendents who do not resemble the majority archetype — 64 percent of superintendents in the U.S. are white men — the scrutiny can feel more intense and the pool of public grace much shallower.
But while superintendents can feel fully visible as public officials, stakeholders frequently experience the opposite: a school district that is inaccessible or unresponsive. In Weld County RE-8, where about 2,500 students hail from rural communities in Colorado, one faith leader told new superintendent Justin Ralston that he had served for nearly 20 years and never once had been invited into a school building. His congregation wanted to help the schools but had no idea how. From the district’s perspective, the door was open. From his, it had never been unlocked.
This Colorado pastor’s experience mirrors broader trends in transparency and public trust. Gallup polling shows that confidence in public schools hovered near 40 percent from the mid-1990s through 2006, dipped to an all-time low of 26 percent in 2014, briefly recovered to 41 percent at the start of the pandemic and has since fallen back to roughly 28 percent, in a tier of public institutions in which only about one-quarter of Americans express high confidence.
A superintendent’s opportunity is to open the system in ways constituents can see and feel — and that means expanding the tent beyond the usual participants and listening more attentively for shared values. Students, teachers and families are the obvious constituencies, but schools exist within a broader ecosystem: faith leaders, business owners, civic organizations and community members whose connection to the school district is indirect but deeply interdependent.
Public Trust
Why does public trust matter? It is the currency superintendents and school boards spend in service of students, whether that means persistent implementation of a strategy that needs more time or taking a heterodox stance to disrupt the status quo. Without public will, without a genuine orientation toward reciprocal relationships across a broad swath of constituents, district leadership is unlikely to have transformative power. Right now, evidence spanning student mental health, academic performance and social connection demands nothing less.
Superintendents’ work as trust builders is both to represent and to shape a community’s vision for its next generation.
The best way to bolster trustworthiness, based on research from organizational management authority David Maister, author of Managing the Professional Service Firm, is to be others-oriented and create intimate settings where neighbors and colleagues feel comfortable to let their guard down. The difference between superficial and deep stakeholder relationships lies in how a leader listens — personally and at scale — and in what that listening ultimately makes possible.
Personal Listening
A one-on-one conversation is the most direct way to build trust. It is also the most conducive setting for uncovering what journalist Amanda Ripley calls the “understory” of any conflict: the values, fears and motivations that lie beneath a person’s stated grievance.
In a group setting, people perform. In a private conversation, especially one held in a neutral, low-power setting like a coffee shop or on a walk together, guards tend to come down.
Harvard’s Ronald Heifetz, a prominent author on public leadership, argues that adaptive work, the kind that requires people to change their own behavior, not just adopt a new program, can only happen inside a “holding environment” with enough relational trust for people to persist through discomfort rather than cut ties when things get hard.
Personal listening is how leaders begin to construct that environment. It signals genuine curiosity rather than superficial engagement, and it gives individuals a chance to tell their own story of connection to or alienation from the school system.
When Ralston arrived in July 2025 as the new superintendent of the 2,500-student Weld County schools in Colorado, he structured his entire entry plan around this practice: more than 300 individual conversations with principals, teachers, staff, board members, faith leaders, business owners and city council members in his first months. He found far more commonality across his community than divisions, and he converted that listening into a strategic plan and an emergent bond campaign to overcome two prior failed votes. (See related story, page page 27.)
Listening at Scale
Even intentionally planned one-on-one conversations cannot reach everyone, and they carry their own biases. Voices heard are not always representative. This is where listening at scale becomes essential, not as a replacement for personal listening but as its complement.
Surveys have gone out to families of students for years. But two specific strategies convert a solid standing habit into a high-value practice.
The first is technology-enabled platforms, many now with embedded AI analysis that allows respondents to see and react to one another’s perspectives. What were one-way channels can become windows into collective sentiment. Parents can see what other parents care about. Teachers can learn where their concerns overlap with those of the business community.
Several platforms enable this kind of reciprocal feedback, turning the school district into a mirror rather than a megaphone. Crucially, this broader denominator of public sentiment helps leaders calibrate a proportional response, resisting the pull to give disproportionate weight to the loudest minority voices or the most recent conversation in the room.
The second strategy is closing the loop. Reflect back on what the district heard and show what it intends to do about it. This is arguably the strongest trust-building move a superintendent can make after any round of listening because it demonstrates that the input was not performative. Community voice converts to visible action, which strengthens the district’s credibility and reliability.
The message shifts from “thank you for your feedback” to “here is what you told us, and here is what we are going to do.” Even when that direction is not supported unanimously or even by a strong consensus, stakeholders feel seen, heard, and respected, deepening their long-term investment.
In Newton, Mass., a well-resourced, high-performing suburban district just outside Boston with nearly 12,000 students, superintendent Anna Nolin chose to survey families who had left the district for private schools. The purpose was not to change their minds or win them back — it was to understand their motivations with genuine curiosity. What were they seeking that Newton’s public schools had not provided?
The move signaled something important, that these families still mattered to the district even after they had opted out and that their perspective carried information worth acting on. For Newton, the collected intelligence helped sharpen the Newton schools’ effort to retain other families. But the act of asking also reinforced a broader message: The district’s circle of listening extended beyond its current enrollment rosters.
Listening as Response
Listening is not only a proactive strategy. It often is the most effective response when conflict escalates. Ripley’s work on the understory is especially useful here. The goal is not to win an argument but to understand what the argument is really about.
A productive dispute achieves one of three things: (1) understanding your own values more clearly; (2) understanding the other person’s motivations; or (3) gaining a deeper sense of the real dilemma. None of those require agreement. All of them keep conflict in a zone where the community can recover.
Anna Nolin (standing at left), superintendent in Newton, Mass., and the district’s central office team formed the Thrive Hive to promote collaboration with the community.
PHOTO COURTESY OF ANNA NOLIN
Jason DeFalco faced exactly this test when he was superintendent of the Blackstone-Millville Regional School District in Massachusetts, a working-class small-town system of 1,450 students. The district was implementing the newly revised state education agency’s PK–12 Health Framework, which includes LGBTQ+ themes, topics and standards. A small group of families became increasingly vocal and increasingly hostile on social media in their opposition.
Rather than respond through official channels or let the conflict play out online, DeFalco invited the most vocal families into his office. He opened with a question that gave them permission to say the thing they needed to say: “What are you truly afraid will happen to your children with these standards in place?” There was no tap dancing. That made it possible to start the real conversation.
The effect was humanizing in both directions. Being in the room with a real person, not a faceless institution to criticize from behind a screen, lowered the temperature. DeFalco took the time to make sure these families did not feel like widgets being managed through a process but rather like valued members of a shared community whose concerns warranted genuine attention.
The meeting did not produce perfect agreement, but it kept a small problem small. It replaced an escalating public narrative with a private, human exchange — exactly the kind of move that builds reciprocal connection while keeping self-orientation low.
Social Infrastructure
Listening, personally and at scale, is how to build a foundation of trust upon which public will can rise and fall. Far from a single tour in the first 100 days, this posture of responsive leadership signals to a diverse set of constituents that this system is open, it sees you and it will not stop asking what you need.
When superintendents commit to that posture, they are not just gathering input for a strategic plan. They are building the public will required to reimagine what students experience every day — the quality of instruction, the breadth of opportunity, the sense that school is a place that sees them, too.
Trust in public education is not the destination. It is the condition that makes it possible to deliver something better for kids.
Caitlin Sullivan is CEO and co-founder of Leading Now in Providence, R.I.
Author
Caitlin SullivanA Listening Playbook for the First 100 Days
Justin Ralston (left), superintendent of Colorado’s Weld County School District RE-8, joined with school board members to create a mural that hangs in their boardroom as a constant reminder of collaboration. PHOTO COURTESY OF WELD RE-8 SCHOOL DISTRICTA first-generation college graduate from a small town in Indiana, Justin Ralston is starting his second year as superintendent of the 2,500-student Weld County School District RE-8 in Colorado, serving mostly rural communities.
His path to the superintendency includes teaching in Washington, D.C., working in refugee camps in East Africa and earning a master’s in social work from Howard University — a background he credits with shaping how he approaches leadership and community relations. During his first year in the district, he prioritized deep listening as the foundation for a new strategic plan and an eventual bond and mill levy campaign, guided by a simple conviction: You cannot lead a community if you don’t know it.
This is an overview of how one Colorado superintendent structured his entry around personal listening and listening at scale.
Before Day 1. Ralston flew to Colorado as soon as he was appointed and met each of his seven board members individually at a local coffee shop. He asked three questions: What’s working well? What’s keeping us from being greater? What land mines should I know about? Every conversation ran two to three hours.
Build the list. He asked board members, his executive assistant (a 30-year district veteran) and community contacts to each submit names of people he should meet. The result was a rolling master list that grew organically throughout the summer.
Meet everyone who wants to be met. Ralston offered every one of the district’s roughly 400 employees a one-on-one, with flexible time slots of 5, 10, 15 or 20 minutes. He completed more than 300 conversations. He met with faith leaders across denominations, city council members in both major cities and the Chamber of Commerce. One faith leader told him he had served the community for 20 years and never had been invited into a school building.
Go where people are. He ran 22 listening sessions across 110 square miles. When a community member pointed out that he had overlooked two smaller communities, he expanded the schedule within days and covered all four communities in subsequent rounds.
Stay accessible. On Day 1, Ralston added an “Ask Superintendent Ralston” link to the header of every district and school web page. Every submission pings him directly, and he has maintained a 48-hour response commitment. When he heard that the district’s bullying form was buried and unresponsive, he added a bullying report link to the same header with immediate notifications to himself and building administrators.
Synthesize and close the loop. He took anonymized notes from every conversation and listening session, then used AI to identify themes across hundreds of pages, cross-checking against his own records. The synthesis became a public 100-day report and formed the backbone of a strategic plan whose four focus areas came directly from what the community told him. (Access it at https://bit.ly/weld-re-8-strategic-plan.)
The payoff. The board now has tasked Ralston with recommending a bond and mill levy, two initiatives the community previously rejected twice. His case is simple: “The shiny buildings don’t really mean a lot if what we’re doing inside of buildings isn’t resonating with the community.” The listening built the trust to make a credible ask.
— Caitlin Sullivan
The Discipline of Seeing from More Than One Seat
By Richard W. Lemons
Richard Lemons, executive director of Partners for Educational Leadership, leads a case study relating to perspectives with the Connecticut Superintendents’ Network.
PHOTO BY BRIDGET NAHABEDIAN OF PARTNERS FOR EDUCATIONAL LEADERSHIP
The work of the superintendency never has been simple. In the current context, every decision seems to hold a bit more charge.
A changed bus route map becomes a referendum on trust while a curriculum adoption becomes a perceived battle over values. In these moments, superintendents are expected to act with clarity, communicate with care and honor the complexity without being paralyzed by it.
One simple leadership practice may help: perspective-taking.
Perspective-taking is the disciplined practice of seeking to understand how a situation looks and feels from another’s position. What might this situation look like from where someone else is standing? What might they fear? What might they be protecting? What prior experiences might make their response understandable, even if I disagree with it?
Beyond Caricature
At a recent meeting of the Connecticut Superintendents’ Network, we borrowed a leadership dilemma from “The Superintendent’s Political Leadership Field Book,” designed by Jennifer Cheatham, Jenny Portillo-Nacu and Marianna Stepniak. The scenario centered on a familiar school district flashpoint, the kind that evokes emotions, strong opinions and clear advocacy.
Small groups of superintendents were asked to inhabit specific assigned roles and speak from those perspectives in the first person and to do so as honestly as possible. That is harder than it sounds.
In public leadership, caricature is always waiting nearby, and it can be heard in our language. We speak of the angry parent, innovation-resistant teacher and “hyper-political” school board member. These labels make our short-term analysis simpler because they reduce complexity. Unfortunately, they quiet real wisdom that could inform our decisions.
Perspective-taking asks leaders to resist reducing people into two-dimensional types. It challenges superintendents to consider that the behavior they find frustrating may be rooted in real experience, deep-seated values or understandable fear. Taking on the perspective of another is not the same as agreeing with their take. It simply means slowing down long enough to see the fuller human picture.
Superintendents are asked to make decisions in conditions where fear, history, identity and trust are already present. A decision can be legally defensible, educationally sound and yet still produce great pain for some. This very complexity is why perspective-taking also requires self-scrutiny. Leaders have to notice the particular lens they bring: the assumptions they hold, what they define as responsible, whose anger they take seriously and whose fear they are likely to dismiss.
A Steady Habit
This leadership practice is straightforward. Place the discipline of perspective-taking into decision-making routines, even before crises emerge. Regularly ask whose view is missing and what their perspective might be.
Carefully examine the possible decision from the vantage of a classroom, kitchen table, bus stop, principal’s office, student’s seat or school board dais. Then step back and consider the implications. What new insights are brought to bear? What might need to be tweaked? Or really revised?
This discipline does not require a grand simulation. It requires the steady habit woven into the day-to-day work. In a time of complexity, superintendents need more than courage and decisiveness. They need disciplined ways to widen what they can see. Perspective-taking is one of those ways. Done well, perspective-taking supports superintendents in making wiser, more humane and more worthy decisions for the communities they serve.
Richard Lemons is executive director for Partners for Educational Leadership and a lecturer in the practice of management at Yale University in New Haven, Conn.
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