What It Means to Be a Thoughtful Leader

Each year, just before the school year begins, I go through a “nesting” period around my home. By methodically cleaning out closets and drawers, I am psychologically preparing for the new school year—it’s a ritual rooted in the hope that by having a more organized home, I will set the table for a smoother school year. 

During my perennial nesting last year, I stumbled upon an email I’d printed (you have to print the good ones) from one of my former graduate school students in which he shared that he had almost completed his first year as a substitute and had just received news that he’d been hired as a full-time teacher. His pride in having his own class was palpable, but so was his gratitude.  

He said he was grateful for what he learned from me in his teaching seminar course, and that what he’d found most impactful was not the theories around teaching reading or successful classroom management strategies, but rather “The simple and honest concern you always showed for us as people first and new teachers second.”  

I taught his course before I was an official school leader, but I believe everyone who works in a school is a leader. Educators lead by example for one another and for our students every day. I still deeply identify as a teacher, especially because I became a principal—and later a head of school––by accident.  

I was fortunate that my years of mentoring and supervising student teachers in graduate school ultimately presented an opportunity to go down this path. Being a principal was not in the plan at the time. Yet, the more I thought about it, the more the prospect made me feel excitement and joy. Despite my lack of formal administrative experience at the time, I knew I could do it.  

I remember being asked in an interview about the first thing I would do if I was hired. Before answering, I paused, thinking it was a trick question. I then responded that I didn’t know what I would do first, but that I would prioritize getting to know the community to understand its needs and potential areas for growth. Despite the seemingly trick question, I got the job. 

After 11 years in school leadership––and as I start my fourth year as head of school––the “I can do this” feeling still propels me. It’s rooted in countless learning opportunities and experiences. And while I know that every leader has their own style, I’ve developed some core beliefs about successful leadership.  

Keys to Thoughtful Leadership 

Leadership is not about any one individual in a school community. It is centered on the people you serve––students, colleagues, the parent community. To lead, you have to care deeply and authentically. You must care about individuals and all they bring to school each day. You cannot fake concern, compassion, or empathy. You must lead with your heart. I would always tell my graduate students that, to be the best teacher, you must have a deep and profound care and love for your students. As a leader, that circle of care grows and grows. 

  • Make time for conversations and really listen. When getting to know your community, it’s not just talking and taking notes. You can only care about people if you consciously get to know them. There is tremendous power in individual conversations, and they take time. An email is often efficient, but it can also be counterproductive if the message should have been spoken. Be deliberate about making space in your schedule for the conversations that will build relationships. To sit in a space and listen, really listen, is incredibly powerful. My first year in an independent school was essentially a listening tour. I got to know my teachers and families—what they were happy with, fearful of, what they wanted to change. I took a ton of notes, asked intentional questions, and when needed, I followed up. While the conversations are the critical first step, if they need to go somewhere, make sure you close the loop.  
  • Build trust. Leading with your heart includes engaging in difficult conversations. They happen often, but these conversations, no matter the topic, are more impactful if they are centered on trust. Trust is ​​built over time with every interaction. Enter into each encounter with an open mind, a kind heart, and a listening ear, while being keenly focused on the person you are spending time with. Do your best to get to know them as a person before addressing any concerns. Colleagues and parents alike may be more willing to listen and reflect on what you’re saying because it’s coming from someone they trust.   
  • Give and take feedback. Feedback is not a one-way street. As a thoughtful leader, you must also be ready and willing to receive feedback. A mentor once told me that if people disagree with you, it shows they care. It is never helpful to sit in a room with colleagues who only say yes to you. Ideally, you can create a team with different personalities and skill sets—people who are confident enough to push each other.  
  • Ask for second opinions. As a new English teacher, I remember deliberately sparking controversy in our discussions. For example, I would make a bold statement about a character, pause deliberately, and then ask the class, “Now who disagrees with me?” Do this with your team. Intentionally ask for other ideas and opinions with regularity. Listen with an open mind and be explicitly open to change. 

We all know the challenges of leadership. Leading a school can be depleting emotionally, physically, and psychologically. There is always more to do, and personally, I never quite feel like I am doing enough. But when I take a moment to extend the same grace to myself that I extend to others, I get to see the good work I put in each day. Just as our faculty and students do, we bring our whole selves to school.  

My former student intentionally italicized honest in his note to me. It serves as a reminder to always be real, genuine, and consistently me.

Colleen R. Pettus

Colleen R. Pettus is head of school at School of the Holy Child in Rye, New York.