Untimely questions

Making time for deep, fundamental questions about purpose and meaning—even when it seems impractical or "untimely" to do so.

School leaders face constant demands for improved test scores, implementation of new initiatives, and addressing immediate crises. Yet philosopher Agnes Callard of the University of Chicago reminds us of the value of what she calls "untimely questions"—those deep, existential inquiries that may seem impractical but ultimately lead to more meaningful growth and innovation. For instructional leaders and education reformers, creating space for these questions can transform school culture from the ground up.

Photo by Jon Tyson on Unsplash

The Socratic method—a questioning approach named after the ancient Greek philosopher—offers practical tools for educational leaders seeking to foster critical thinking. Rather than positioning the leader as the expert with all the answers, this approach encourages collaborative exploration through strategic questioning. When principals and instructional coaches adopt this stance, they model the kind of intellectual curiosity we hope to develop in both teachers and students.

While Western philosophical traditions offer valuable insights, the wisdom of Persian Sufi mystics like Rumi provides a complementary perspective on transformative learning. Rumi's poetry and teachings emphasize that true education involves not just acquiring information but experiencing personal transformation. This holistic vision challenges education reformers to consider how schools might nurture not only academic achievement but also deeper human development and meaning-making.

Untimely questions

As Callard notes in her interview about her book "Open Socrates," we tend to avoid deep questions because of "the overwhelming ethos of urgency" in our daily lives. In schools, this manifests as prioritizing immediate solutions over thoughtful inquiry. However, when principals and district leaders make space for questions like "What kind of citizens are we preparing?" or "How does this approach honor students' humanity?", they open doorways to more meaningful reform efforts.

For busy administrators, finding time for such reflection might seem impossible. Callard offers practical advice: look for the openings in conversations you're already having. Rather than adding more meetings, education leaders can transform existing interactions by asking follow-up questions that probe beneath surface-level discussions. During faculty meetings or classroom observations, thoughtful questions like "What assumptions underlie this approach?" can shift the conversation toward deeper examination of practices.

Education reformers often focus on implementing specific programs or achieving measurable outcomes. However, Callard's work suggests that meaningful change requires engaging with fundamental questions about purpose and values. When district leaders invite teachers and community members to wrestle with questions about the aims of education—not as a one-time activity but as an ongoing practice—they build a stronger foundation for sustainable improvement than any single initiative could provide.

The Socratic Method

The Stanford Encyclopedia of Philosophy describes how Socrates engaged in dialogue with fellow Athenians, challenging their assumptions and helping them recognize the limits of their knowledge. Unlike the "sage on the stage" model of leadership, the Socratic method positions the leader as a facilitator who draws out insights through carefully structured questions. For principals observing classrooms or leading professional development, this approach shifts the dynamic from evaluation to collaborative exploration.

In practice, educational leaders can implement Socratic questioning by asking teachers to explain their reasoning, consider alternatives, and examine evidence. Rather than immediately offering solutions during coaching conversations, effective instructional leaders might ask: "What led you to choose this approach?" or "How might we look at this situation differently?" These questions demonstrate respect for teachers' professional judgment while encouraging deeper reflection on practice.

School reform initiatives often falter because they're imposed from above without meaningful engagement from those expected to implement them. The Socratic method offers an alternative approach where leaders use questions to build shared understanding and ownership. When implementing new curricula or instructional frameworks, leaders can create forums where teachers examine assumptions, consider implications, and connect initiatives to their own values and experiences. This approach transforms compliance into genuine commitment.

Rumi's Sufism

Rumi, as described in Aliaj's "Mystical Quest in Persian Sufis," viewed learning as a transformative journey toward personal awakening. For today's instructional leaders, this perspective offers a valuable counterbalance to technocratic approaches focused solely on measurable outcomes. When principals encourage teachers to connect their professional practice with their deeper values and sense of purpose, they tap into powerful motivational forces that technical training alone cannot access.

Education reformers can draw practical inspiration from Rumi's emphasis on the power of love as a motivating force for growth. In her analysis of Rumi's work, Aliaj notes that "love gives strength and vigor to endure all the sufferings, grief and pain." Similarly, effective school leaders recognize that teachers need more than new techniques; they need to reconnect with their passion for education and their care for students. Professional development that acknowledges and nurtures this emotional dimension creates more resilient educators.

School leaders might incorporate Rumi's wisdom by creating reflective practices that engage both intellect and heart. Simple rituals like beginning meetings with meaningful quotes or personal reflections, establishing regular check-ins about educators' sense of purpose, or encouraging teachers to share stories of transformation can shift school culture. Rather than treating these as separate from "real work," effective leaders integrate reflection into the fabric of school improvement.

Implications for practice

For education reformers and school leaders, implementing these philosophical approaches requires concrete strategies. First, leaders can audit their communication patterns, noting how often they make statements versus asking genuine questions. By intentionally shifting toward more inquiry-based leadership, principals create a culture where questioning becomes normalized. As Callard suggests, this doesn't require adding more to already full plates—it means approaching existing responsibilities with a different mindset.

Second, instructional leaders can redesign professional learning to incorporate both Socratic dialogue and reflective practices. Rather than workshops that simply deliver information, effective professional development engages educators in examining their assumptions, sharing diverse perspectives, and connecting new approaches to their core values. Leaders might structure conversations around essential questions, use protocols that promote deep listening, and create opportunities for personal reflection alongside technical learning.

Finally, education reformers should recognize that lasting change emerges from communities engaged in ongoing inquiry rather than from implementing predetermined solutions. By establishing regular forums where stakeholders can explore untimely questions together—perhaps through book studies, community conversations, or structured dialogues—leaders build the collective capacity needed for sustainable improvement. As both Socrates and Rumi would affirm, the most powerful educational transformations begin not with answers but with questions that awaken our shared humanity.

References

Aliaj, Majlona. "Mystical Quest in Persian Sufis." ResearchGate Preprint, January 2021.

Callard, Agnes. "Open Socrates: The Case for a Philosophical Life" (Interview Q&A on UChicago Humanities). March 2025.

Stanford Encyclopedia of Philosophy. "Socrates." Retrieved from https://plato.stanford.edu/entries/socrates/