Question 2: Where Am I Saying ‘Yes’ When I Should Be Saying ‘No’?

This might be the most difficult question on the list, but it’s also potentially the most transformative. As one experienced head noted, “Leaders are hired to make hard decisions, which will inevitably get mixed reviews from different constituencies. Very rarely will leadership get 100% backing all the time.”

Independent school leaders are generous people by nature—we want to support every initiative, attend every event, and solve every problem. But this impulse, while admirable, can lead to decision fatigue and scattered focus.

Look at your calendar from last year. Where did you spend time that didn’t align with your core leadership purpose? What meetings could you have skipped? What projects could have been delegated or eliminated entirely?

Consider how much time you might be spending in meetings that could be emails or that simply don’t require your presence. Leaders often discover they’re losing ten or more hours a week to obligations that don’t advance their core purpose. When you start saying no to these commitments, you gain time for strategic thinking and classroom visits that actually move the school forward.

Practical reflection exercise: List everything you said “yes” to last year that you wish you had declined. Look for patterns—are you defaulting to yes out of guilt, habit, or fear of disappointing others?

Question 3: How Will I Prioritize Relationships Over Tasks This Year?

Here’s something I’ve learned from working in and with independent schools: the quality of relationships determines the success of every initiative. Research with independent school leaders consistently identifies “maintaining relationships among key constituencies” as one of the most important skills for effective leadership.

Yet it’s easy to get caught in task-management mode, especially when August deadlines loom. The most successful leaders I’ve worked with are intentional about protecting time for relationship building, even when—especially when—the pressure is on.

Think about your key constituencies: faculty, students, parents, trustees, colleagues. Which relationships energized you last year? Which felt strained or neglected? What patterns do you notice in your relationship management?

Partnerships with other local heads can become essential support systems. What might begin as quick calls for reassurance and camaraderie can evolve into friendships built on trust—relationships that sustain you through challenging times. These connections often prove more valuable than formal professional development.

Practical reflection exercise: Identify three key relationships you want to invest in this year. Schedule specific time for these connections before your calendar fills up with urgent tasks.

Question 4: What Support Systems Do I Need to Sustain My Leadership?

Leadership can be isolating, particularly in independent schools where the head or division director often feels responsible for everything. Successful sustained school improvement requires supportive leadership, planning, and community commitment, but who’s supporting the leader?

This question invites you to think honestly about what you need to lead effectively. Do you need a mentor? A peer network? Professional development? Better boundaries between work and personal life? More delegation training for your team?

I’ve seen too many talented leaders burn out because they tried to carry everything themselves. The strongest leaders I know are strategic about building their support systems—they have coaches, they participate in leadership cohorts, they delegate meaningfully, and they take care of their physical and mental health.

Practical reflection exercise: Map your current support systems. Where are the gaps? What one addition to your support network would have the greatest impact on your leadership effectiveness?

Question 5: How Will I Know If This Year Is Successful?

This final question is about creating clarity around success metrics that actually matter to you and your school community. It’s easy to get caught up in surface-level indicators—enrollment numbers, test scores, fundraising totals—while missing the deeper measures of educational excellence.

Effective leaders provide clear vision and sense of direction, prioritizing and focusing staff attention on what is important. But that requires first getting clear on what success looks like for your specific context.

Consider both quantitative and qualitative measures. Yes, enrollment and retention matter, but what about faculty satisfaction? Student engagement? Community connection? Your own sense of fulfillment and growth as a leader?

One dean I worked with defined success as “creating an environment where students feel comfortable taking intellectual risks.” That became her North Star, influencing everything from classroom observations to parent communication strategies.

Practical reflection exercise: Define three success indicators for this year—one quantitative, one qualitative, and one personal. Write them down and schedule quarterly check-ins to assess progress.

Making Reflection a Practice, Not Just a Summer Exercise

While this deep reflection is crucial before the school year begins, creating time for reflection isn’t something that’s only reserved for the quieter months of leadership. It’s something that benefits us all year round.

Consider establishing a weekly reflection practice using simpler questions: “What went well this week?” “What could have gone better?” “What do I want to focus on next week?” These questions can help you remember the lessons from the past week and use them to inform the next.

The Power of Documented Reflection

Here’s a practical tip I learned the hard way: don’t just think through these questions—write down your answers. Having your answers written down will give you the context you need to take action. There’s something powerful about committing reflections to paper that transforms vague thoughts into actionable insights.

I keep a leadership journal that I return to throughout the year. Some entries are longer reflections like these five questions; others are quick notes about difficult conversations or successful initiatives. Over time, patterns emerge that help me grow as a leader.

Building Accountability Into Your Process

Reflection without accountability often remains just that—reflection. Consider sharing your insights from these questions with a trusted colleague, mentor, or leadership coach. Sharing our reflections with our peers keeps us accountable and also helps us realize we’re not alone in our thoughts.

You might also schedule mid-year check-ins with yourself to revisit these questions. How has your leadership purpose evolved? Are you maintaining better boundaries? Are your support systems serving you well?

Creating Space for What Matters Most

As you work through these questions, you might feel overwhelmed by all the ways you want to grow and improve. That’s normal—it’s a sign that you’re taking your leadership seriously. But remember: the goal isn’t perfection; it’s intentionality.

Successful leaders are constantly reflecting upon and evaluating their decisions, committed to an ongoing process of problem solving and solution generating. This kind of reflective practice is what separates reactive leadership from strategic leadership.