How School Leaders Can Make High-Stakes Decisions With Clarity and Empathy 

Against a backdrop of unrelenting day-to-day problem solving, from bus delays and staffing issues to student discipline, school leaders must also routinely make difficult, high-stakes decisions that may significantly impact student learning and teacher well-being. 

While it’s easy to feel “lost and overwhelmed in the face of that responsibility,” says high school principal Jessica Cabeen, it’s important to slow down enough to consider the ripple effects tough decisions may create in the school ecosystem. In these moments, having a “framework that acknowledges the interconnectedness of modern challenges and supports principled, decisive action—even when every option feels impossible,” can be game changing, writes C-suite executive and author, Daisy Auger-Domínguez in the Harvard Business Review.

Ultimately, no decision will ever satisfy all stakeholders—especially in communities as diverse as schools. Whether leaders are deciding how to integrate AI into teacher workflows, overhauling scheduling or shifting to an entirely new grading system, decisions like these shape daily life in a school, carry long-term consequences, and often provoke strong emotional responses from teachers, students, and families.

While dealing with hard feelings and pushback is certainly part of the leadership job, careless or poorly handled decisionmaking can damage trust, strain relationships, and erode school culture, says Dan Fisher, an elementary school principal. At the same time, vacillating between positions or allowing “the loudest or pushiest people in the building” to hijack the process, Fisher says, is also damaging, resulting in leaders losing credibility and direction. “It is important to remember,” Fisher writes, “that your job as a school administrator is to be comfortable with being uncomfortable.”

Drawing on insights from Auger-Domínguez, school leaders, and communication experts, the strategies below offer a framework to help principals and administrators navigate high-stakes decisions.

Map Out Trade-Offs 

Big decisions shouldn’t be made in a vacuum without fully considering the risks and trade-offs involved, writes Auger-Domínguez. Taking the time to map out trade-offs helps leaders “surface hidden dynamics, including the hard issues people often avoid, so they can tackle what matters most.”

Responding to a set of targeted questions designed to reveal second-order consequences of a decision that might not be immediately obvious can be a productive starting point. The goal is to get ahead of potential pushback, examine blind spots, reduce confusion, and “adjust language, clarify intent, and prepare to answer tough questions with empathy and transparency,” Auger-Domínguez writes. She suggests the following questions as a starting point: 

• If we decide ____, what concerns might immediately come up? 
• What trade-offs are we willing to accept as a result of this decision—and why? 
• What operational or reputational risks do you think we’re overlooking? 

For example, when former high school principal Neil Anderson decided to push back the start time of his high school to allow teens to get the sleep that research suggests they need, the feedback he received from parents, teachers, and athletic coaches was “raw.” Anderson said he listened intently to the feedback, which clarified trade-offs around athletics schedules, instructional planning, and early drop-off needs. Those concerns helped him refine his plans and strengthen his case for the benefits of sleep for students’ mental health, alertness, and academic success.

Raising and responding directly to the trade-offs upfront helped the community understand both the benefits of the change and its limitations, Anderson said, adding that often stakeholders “come to principals to be the communicators and sensemakers for them.” 

Pressure-Test With Key Partners

While it is up to leaders to make decisions, the thinking behind them shouldn’t happen in silos. Invite targeted input from trusted partners and stakeholders—fellow administrators, teachers, students, and maybe even families depending on the decision at hand—before settling on a direction that will affect them. 

School leaders can structure these conversations with a few guiding questions: 

• Does anything about this decision feel at odds with our school’s goals? 
• What concerns or challenges does this raise from your perspective? 
• What unintended consequences should we be prepared for?

Pressure-testing a plan won’t magically eliminate all tension in your school community, but the effort can reduce the perception that a decision was rushed or imposed from the top down, Auger-Domínguez notes. Within any organization, research shows that this type of negative perception can trigger cynicism, doubt, and distrust, instead of building employee buy-in. 

When leaders are able to openly discuss differences of opinion, rather than avoiding them, the conversation can shift into productive territory, note Manhattanville College education professor Robert Feirsen and former principal Seth Weitzman. Phrases like “This is where we agree, and this is where we disagree,” for example, help clarify differences and often reveal more common ground than expected. In a discussion about a new AI policy for student writing, for example, a principal might say: “We agree that students can use AI to gather information and brainstorm ideas, and that our goal is to promote critical thinking. Where we disagree is whether AI should be used to revise writing.” 

At some point, school leaders must close the window of discussion and make decisions that might not be unanimously popular, Fisher says. “Occasionally upsetting people who have enjoyed certain privileges or who have gotten used to a particular way of doing things is your job,” Fisher writes. “Of course, you can do this work in a way that is transparent and kind (and you should), but the work needs to get done.” 

Fisher says that a good final question to ask yourself is: “Is this decision what is best for kids?” If the answer is yes, then “your best teachers will come to recognize and appreciate your child-centered thinking over time.”

Communicate Clearly—and with Empathy

When coaching school leaders on how to communicate tough decisions, Matt Abrahams, a lecturer in strategic communication at Stanford’s Graduate School of Business and a former teacher, leans on his mother’s wise words: “Tell the time, don’t build the clock.” In other words, if a decision is likely to disappoint staff—such as budget cuts, staffing changes, or policy shifts—Abrahams says leaders shouldn’t bury the lead, even if the impulse is to somehow soften the message, or perhaps avoid explaining potentially unpopular details.

When leaders fail to clearly explain decisions and the reasons behind them, “people fill in the gaps themselves,” writes Auger-Domínguez—which is how “rumors and misinformation take hold.” Auger-Domínguez recommends the following communication guidelines: 

• Be specific: Rather than saying, “We’re making some adjustments,” say “We’re reducing discretionary spending next semester to preserve classroom staffing.”

• Own uncertainty: If there is real ambiguity around how plans will unfold, be upfront: “We’re in the messy middle. I don’t have every answer yet, but I’ll keep you updated as we learn more.” 

• Invite feedback: Ask what questions or concerns staff have, and what needs further clarification.

• Offer hope: Even when a decision is unpopular, leaders can acknowledge difficulty while pointing forward: “This is tough, but it’s also a chance to build something better together.”

The goal, Abrahams says, isn’t one-size-fits-all communication, but distinct messages calibrated to the needs of each group affected by the decision. While the core decision may stay the same, what different groups need to hear—and how they need to hear it—may vary. Questions to consider: 

• Who am I talking to, and what do they need to understand right now? 
• How do I want them to feel? 
• What do I want them to do next?

After adopting a new instructional policy, for example, teachers may need concrete guidance on how it affects lesson planning, pacing, or assessment, while families only need a high-level explanation of the change and how it affects students. Clear communication, Abrahams notes, doesn’t end with general buy-in, but with specific, actionable next steps for each group.

Timing Matters

Major shifts—such as adopting new instructional tools, or rolling out significant policies—often will require advance planning so that they align with the school year and support, rather than disrupt, classroom learning. 

When leaders in the Hancock Place School District in Missouri decided to license three new AI tools for teacher use, for example, they didn’t drop the tools into classrooms midyear when teachers were already juggling heavy instructional demands. Instead, they used the summer to offer paid, hands-on teacher training led by edtech experts and representatives from the tools themselves, giving teachers time to develop concrete classroom use cases they could pilot and refine with support from school leaders.

The goal of this timeline, said Superintendent Kevin Carl, was to ensure teachers had the space to understand the tools well before they were expected to use them—and felt empowered to experiment thoughtfully. “When I as a teacher can be creative,” Carl said, “that’s the game changer.” 

When leaders align big decisions with the natural cadence of the school year, they give teachers the time, clarity, and confidence needed to help make big changes stick.