Yesterday, a room full of superintendents did something that looks small on paper and feels deceptively simple in real time: we practiced taking another person’s perspective.
Not as a feel-good exercise. Not as a political tactic. As a leadership discipline.
We began, as we often do, by making space to arrive. A short mindfulness protocol invited people to notice what they were carrying—what was in their heads, what was in their hearts—and to decide, intentionally, what could be set at the margin (for now) so they could be present for the work ahead. It was quiet. It was human. And it set the tone for a day organized around one core question: How does a superintendent use the practice of perspective-taking to make change that leads to a better future?
Perspective-taking as a “brain hack” (and why leaders should care)
Our pre-reading framed perspective-taking in unusually practical terms, not as something “soft,” but as a capability with real cognitive and organizational payoff. Michael Platt and colleagues describe it as a means of accessing more information in complex situations—and of activating the parts of our thinking tied to imagination, exploration, and creative problem-solving.
In other words, getting inside someone else’s head can help you get outside your own habits.
That matters in the superintendency because so much of the work happens under conditions that reward speed, decisiveness, and certainty—conditions that can quietly narrow what we notice, who we hear, and what we assume is “obvious.” Perspective-taking interrupts that narrowing. It slows the mind down long enough to widen the field.
The simulation: a flashpoint, and the temptation to caricature
The heart of the morning was a simulation built around a high school flashpoint—one of those situations that can ignite strong reactions quickly and pull adults into familiar grooves: certainty, defensiveness, blame, fear, moral outrage, political calculation, exhaustion.
The simulation comes from The Superintendent’s Political Leadership Fieldbook and was designed by Jennifer Perry Cheatham, Jenny Portillo-Nacu, and Marianna Stepniak. It is built to feel uncomfortably familiar to superintendents. Yesterday, it did. But it also required something harder: stepping out of our “usual selves,” setting down our preferred storyline long enough to inhabit someone else’s.
Small groups were asked to step into different roles—people implicated in the story—and prepare to speak from those perspectives: What might this person be thinking? What might they be feeling? What experiences might be shaping their stance? What do they need? What do they fear? What do they want others to understand?
Then, in groups, people “dramatized” those viewpoints—speaking in the first person—before stepping back to synthesize: What do we learn when we hold these perspectives side by side? What changes about the way we lead? What questions become unavoidable?
What the debrief surfaced
The ensuing conversation was candid about the difficulty of this work. Here’s what emerged that felt most important:
- There is power in taking a perspective. There is more power in taking multiple perspectives. Moving from one role to another—flipping the lens—forces the mind to loosen its grip on a single storyline. It expands not only empathy but options.
- Caricature is the default risk. If we do not do this work with rigor and care, we flatten people into types: the angry parent, the out-of-touch teacher, the political board member, the naïve student, the opportunistic community member. Caricature is easy. Honest rendering is hard. And honest rendering is the point.
- Superintendents are often asked to hold competing truths. Not to “both-sides” moral questions into mush, but to recognize that multiple truths can coexist in the same moment—especially truths about impact, fear, history, identity, and trust. A rationally sound decision can still cause harm if leaders fail to anticipate how it will be experienced by those who have lived through earlier versions of the same story.
- Bias walks into the room before we do. Even when we attempt perspective-taking, we carry assumptions shaped by our own lived experience: what “good” looks like, what “responsibility” means, what counts as “reasonable,” and who is “credible.” The practice is not only “try to understand others.” It is also “notice the lens through which you are trying.”
- Empathy can be used for understanding—or for maneuvering. This distinction landed. There is a version of perspective-taking that is essentially strategic: I will understand you so I can predict you, manage you, or move you toward my preferred outcome. And there is a version that is relational and epistemic: I will understand you because I may not yet understand the whole truth—and because your experience matters, even if it complicates my plan. Leaders feel the pull toward both. Naming that tension is part of the work.
- Scar tissue is real. One superintendent offered a truth many leaders carry quietly: after enough public attacks—especially attacks that feel personal—your nervous system learns a protective reflex. That reflex can make genuine empathy harder in the moment you need it most. This is not a moral failure. It is a human consequence. Naming it helps leaders plan for it, rather than being captured by it.
- The debrief is not optional. The exercise is not complete when everyone has spoken from their assumed role. The essential work is in the synthesis: What is the amalgam of these perspectives? What patterns do we see? What are we missing? What do we now need to test in the real world? What does this mean for pace, communication, sequencing, support, and accountability?
Back in your district
So what might this mean in practice?
Build perspective-taking into the routine of decision-making—not only for crises. Before big decisions, ask: Whose perspectives are we missing? What is the strongest argument against our current plan? What would this look like from the classroom, the kitchen, the bus stop, the student’s seat, the parent’s night shift, the principal’s inbox, the board’s dais?
Practice what one superintendent yesterday called “anti-caricature.” When your team describes a stakeholder group, listen for flattening language. Then intervene: What is the most generous, honest version of this perspective? What experiences might make this stance rational from their point of view? What values might be underneath the behavior we dislike?
And after mapping perspectives, do not stop at “interesting.” Debrief for synthesis, not just sharing. Ask: What changes now? What do we need to learn next? What would we do differently if we took these perspectives seriously? What support, pacing, and sequencing would honor what we heard?
Yesterday reminded me that leadership is often a game of inches. Sometimes the most consequential work is not a sweeping reform or a bold new initiative. Sometimes it is a micro-practice—done consistently—that changes the temperature in the room, widens what people can see, and makes a better future more possible.
Sometimes the practice begins with a simple decision: to pause, to imagine, and to try, with discipline, to tell the truth about someone else’s truth.
In Partnership,
Richard Lemons
Executive Director
Partners for Educational Leadership
rlemons@partnersforel.org


