By Ken Spero
The Most Complex Leadership Job in the World
For more than 35 years, I’ve had countless conversations with leaders—both inside and outside of education—about the challenges that keep them up at night. Over the last decade, in my work with SchoolSims where I have been focused on the challenges in Education, I’ve come to believe that leading a school or district is among the most demanding leadership roles anywhere.
Unlike the corporate world, where success can be measured in market share, margins, productivity, or shareholder value, education operates in a realm where there are few truly right answers. Every decision is layered with competing priorities, human emotions, and values-based trade-offs that directly affect children, families, staff, and communities—stakeholders who are rarely, if ever, fully aligned.
It’s striking how much of our leadership wisdom still comes from business literature. Having worked with executives across industries and around the world, I’m convinced that many otherwise successful business leaders would find leading a school or district very challenging. In education, uncertainty isn’t an occasional disruption—it’s the daily reality.
That’s why I found the recent Harvard Business Review article, “Our Favorite Management Tips on Leading Through Uncertainty” (HBR Editors, 2025), so resonant. While written for business audiences, its core insights—about courage, clarity, simplification, and resilience—speak directly to what today’s school leaders experience.
The challenge isn’t just knowing these lessons, but living them under the pressure of real-world decisions. That’s where Sims-centric leadership development becomes essential. It offers a safe space to rehearse decision-making amid ambiguity, to experiment and fail forward, and to learn from consequences before they happen.
The HBR collection distills several key principles that, when adapted to K–12 leadership, can strengthen both individual and collective capacity to navigate uncertainty with confidence and hope.
- Courage Is the Antidote to Fear
“Courageous leaders don’t wait for clarity—they create it.”
— Ranjay Gulati, “Now Is the Time for Courage,” HBR (2025)
In schools, that courage looks like making a difficult personnel decision, addressing a parent controversy, or standing up for inclusion even when public sentiment wavers. It’s not about fearlessness—it’s about acting in service of a purpose even when fear is present.
SchoolSims simulations provide a safe environment to practice this courage: reframing fear through story, testing moral resolve, and learning how to make principled decisions when no option feels entirely safe.
- Strategic Hibernation: Holding Steady in Political Whiplash
Christopher Marquis’ concept of “strategic hibernation” is especially relevant in education. When policy shifts, funding cycles tighten, or community pressures mount, school leaders may need to pause—without abandoning their mission. Marquis emphasizes maintaining core assets and preserving flexibility during headwinds.
For schools, that means protecting culture, keeping key teams intact, and sustaining student-centered priorities even amid external volatility. Sims allow leaders to test these delicate calibrations—how to stay visible yet steady, patient yet principled.
Source: “Is This a Moment for Strategic Hibernation?”, Christopher Marquis, HBR (2025)
- Communicating Through Ambiguity
Rebecca Knight’s assertion that “your team doesn’t need spin—they need clarity” could easily headline a superintendent’s leadership philosophy. Educators, staff, and families look for steady truth, not polished certainty.
Knight’s guidance to acknowledge what’s working, invite questions, and model calm transparency translates perfectly to faculty meetings, board communications, and community forums. Through Sims, leaders can practice this balance—learning to communicate with honesty and empathy when the answers aren’t yet clear, an essential skill for trust-building in anxious times.
Source: “How to Communicate with Your Team When Business Is Bad”, Rebecca Knight, HBR (2025)
- Subtraction and Simplification
Vijay Govindarajan and colleagues introduce the idea of “strategic subtraction”—removing what no longer adds value. In schools, where initiatives often multiply faster than capacity, this principle can be transformative. Doing less, better—clarifying priorities and cutting complexity—builds resilience and focus.
Sims let leaders explore the ripple effects of those decisions: what happens when a program is paused, a committee dissolved, or a tradition reimagined? The practice reveals that simplification, far from weakness, is a hallmark of disciplined leadership.
Source: “In Turbulent Times, Consider Strategic Subtraction”, Vijay Govindarajan et al., HBR (2025)
- Ask Better Questions
Cheryl Strauss Einhorn’s framework—asking questions that expand rather than narrow thinking—is tailor-made for education. Her four prompts invite reflection that transcends crisis:
- What decision today will still make sense a year from now?
- If this became a leadership case study, what would it teach?
- What if this isn’t the storm—what if it’s the climate?
- What’s the cost of waiting?
These prompts can shape leadership conversations, board discussions, or principal reflection journals. In Sims, they spark deeper dialogue, reframing uncertainty as opportunity for growth and ethical clarity.
Source: “In Uncertain Times, Ask These Questions Before You Make a Decision”, Cheryl Strauss Einhorn, HBR (2025)
- Turning Disruption into Practice
Rae Ringel and Lisa Kay Solomon highlight that “disruption is constant.” For school leaders, the pandemic confirmed this truth—and introduced lasting shifts in instructional models, workforce dynamics, and community expectations.
This aligns perfectly with the SchoolSims philosophy: leadership development through repeated cycles of testing, reflection, and adjustment—turning disruption into deliberate practice.
Source: “5 Pandemic-Era Lessons on Leading Through Drastic Change”, Rae Ringel & Lisa Kay Solomon, HBR (2025)
- Steadying the Team
Ranjay Gulati’s reminder that leadership is “as emotional as it is strategic” applies profoundly in schools. A leader’s tone and calm can ripple through classrooms and shape the collective climate. Modeling poise and authenticity builds the trust that sustains teams through challenge and change.
Sims help leaders experience this ripple effect—how words, gestures, or decisions can either ground or unsettle a staff—and reflect on how to lead with composure and consistency.
Source: “How to Keep Your Team’s Spirits Up in Anxious Times”, Ranjay Gulati, HBR (2025)
From Insight to Impact: Practicing Leadership Under Uncertainty
The HBR editors remind us that uncertainty is not an interruption of leadership—it’s the essence of it. Resilient leaders, in education and beyond, are distinguished not by their ability to predict the future but by their capacity to act with clarity, courage, and purpose when the future is unknowable.
SchoolSims simulations translate these leadership ideals into lived practice. By stepping into realistic, narrative-based decision environments, aspiring and sitting school leaders can experience complexity before confronting it, test their instincts, learn from consequences, and build the calm confidence their schools—and students—deserve.
Because in the end, leadership in education isn’t about eliminating uncertainty. It’s about cultivating the wisdom, resilience, and hope to lead through it.
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