Step Into a Principal’s Shoes: What Aspiring Leaders Learn By Shadowing

As an educator, you already know schools move fast—and because of that, you move fast. You’ve juggled back-to-back demands and seen your principal do the same. 

But when you shadow a principal—whether for a day as part of your principal preparation program—you gain an entirely different perspective on leadership. You start to see how every urgent issue, hallway conversation, and schedule change is connected to the work of leading the entire school.

Principal shadowing offers aspiring leaders the chance to observe tough decisions in real time, to notice the relationships and collaboration that make those decisions possible, notice the relationships that make those decisions possible, and understand how the principalship requires both day-to-day management and long-term vision. 

What to expect during principal shadowing

While every school and leader is different, any shadowing day will be full, fast-paced, and unpredictable. Because you’re often side-by-side with the principal during these days, you’ll see the principal shift from greeting students at the door, to a discussion with a teacher, to solving a facilities issue, to preparing for a board meeting—all before lunch. 

You’ll also get a behind-the-scenes look at the mix of visible and invisible leadership work that you’ll do as a future principal. Some moments are big and public—leading a staff meeting, or being front and center at a school assembly—while others are quiet but just as important, like a quick check-in with a student. 

ProTip: Treat every moment as a learning opportunity. Take in not just what’s happening, but how it’s handled and the tone that’s been set. It’s those details that bring the biggest leadership lessons. 

Why You Should Shadow More Than One Principal

No two principals lead the same way. Two principals will have completely different ways of dealing with staff issues or instructional challenges. A high school principal’s day looks different from an elementary principal’s. Rural and urban principals also face different sets of resources, expectations, and community dynamics.

That’s why shadowing in more than one setting—and with more than one leader—is valuable. Not only will you see a variety of leadership styles and the way context shapes decisions, but you’ll also start to notice the common threads: the core priorities, relationship skills, and steady presence that effective principals bring to every situation.
‍

{{light-hex}}

‍

How to make the most of your shadowing experience

The best shadowing experiences are intentional. We’ve created this “before/during/after” framework to help you prepare and engage fully in your shadowing: 

Before your shadowing day:

• Research the school. As we mentioned above, we suggest shadowing more than one principal, so it’s a great idea to review the school’s demographics, academic performance, programs, staff listings, and any public-facing strategic or improvement plans. This information will help you better interpret what you see during your day.
  
  
• Clarify your own goals. Do a little self-reflection. What are you most wanting to learn or hoping to get out of these shadowing experiences? It might be more big-picture items like culture building or a principal’s insight on instructional leadership strategy, or more tactical skills like time management, handling a difficult conversation, or prioritizing competing demands in the middle of a busy day.
  
  
• Prepare a series of focused questions. Go beyond asking the basic “So, what does a typical day look like?” question. Instead, think about specific situations you most want insight on and frame your questions around them. You might ask how they decide what gets delegated, how they follow up after classroom visits, or what systems help them stay organized when the day gets unpredictable.

During your shadowing day:

• Watch the “how,” not just the “what.” The order of a principal’s day is interesting, sure, but the bigger lessons are in how each moment is handled. Pay attention to tone, body language, pacing, and how the principal shifts seamlessly between audiences, from a student in the hallway to a team of teachers to a district leader.
  
  
• Look for patterns and systems. As the day unfolds, notice which challenges come up more than once and how they’re addressed. Are there proactive systems in place that keep issues from escalating? Do certain routines help the principal maintain momentum? These patterns can reveal a lot about how effective leaders manage recurring demands.
  
  
• Study relationships in action. Some of the most important leadership work happens in quick, informal interactions. Watch how the principal builds trust with staff, connects with students, and engages with families. Notice how those relationships create a foundation for addressing tougher issues when they arise.

After your shadowing day: 

• Reflect and capture your takeaways immediately. Set aside time to jot down your key observations—the moments that surprised you, challenged your assumptions, or stood out as great examples of leadership. The pace of the day can make it easy to forget details, so get them on paper while they’re fresh.
  
  
• Turn insights into action. Don’t let your notes sit in a folder. Identify two or three specific strategies, habits, or mindsets you can begin applying in your current role. Whether it’s a way of structuring feedback, managing time, or greeting students, put your learning into practice quickly so it sticks.
  
  
• Close the loop, and build the relationship. Send a thank-you note or email that shares one or two concrete things you learned from your shadowing experience—it’s never a bad idea to show appreciation, and it’s also an opportunity to grow the connection if that’s what you’re looking for. If the relationship feels like a good fit, see if they’d be open to occasional check-ins or mentoring as you move toward the principalship.

From observation to action

Shadowing a principal isn’t about memorizing someone else’s playbook. It’s about noticing the small moves that add up to big impact, and using what you’ve seen to shape your own approach to leadership. Every conversation, every decision, and every hallway moment is a chance to learn.

The real value comes later, when those observations start to influence how you lead from your current role. Maybe you experiment with a new way to structure team meetings, greet students in the morning, or handle an unexpected challenge. These tiny but intentional shifts—rooted in what you saw and learned—can start shaping you into the kind of school principal your future community will need.

Shadowing is one of the many real-world learning experiences included in the New Leaders National Aspiring Principals Fellowship. You’ll gain hands-on insight into the principalship, paired with job-embedded coaching and a supportive peer network. Learn more about the Fellowship here.
‍

{{light-hex}}