Leadership Conversations: Seeking the Right Moment
I’ve had the privilege to meet and connect with so many leaders over the arc of my career. It was the moment in 2016 at the People of Color Conference when the heads of color were invited to the stage that was the flashpoint for my current leadership pursuits. Their presence on stage was a beacon of possibility. Then they asked for any aspiring leaders in the audience to stand. I recall, sitting in the darkness of the room, pausing and wondering if I should stand. I most certainly wanted to, but there was this lingering question in my mind of the legitimacy of my aspirations.
Later at that conference I would meet an Asian head of school who listened to my wonderings about school leadership and how someone like me could ever think about being a head of school. He looked me squarely in the eyes and just said, “go for it. there’s no reason you shouldn’t” and that it was ridiculous to doubt the possibility. He was the first of many to provide a supportive consult.
Each leader is different and there are no two journeys or pathways that are the same. As I’ve continued to explore and build my capacity as a leader, I’ve met with a few people regularly. The one person who has provided the most consistent and grounded support is my assistant head of school. Our relationship began when she was our interim upper school director. We would meet and have conversations about the history of the school, the climate of our colleagues and students, and about our professional experiences.
In one of our recent conversations, we talked about the diversity of advice that I have received. Some people have urged me to pursue a headship, but then others who recommend and interim step as a school administrator in academics. it is a fascinating tale of two stories and approaches.
Does the source of the advice matter? Is it a recruiter? Does it make it different if its a recruiter that I’ve know professionally or personally otherwise? Is it my head of school, former head of school., board colleagues? Trusted colleague?
When we talk about my leadership capacity, often we talk about the good work that I’ve done, but also the sobering reality of independent school hiring and recruitment, and the litmus for change. I tend to present as a progressive candidate, and a new type of school leader. My professional experience and skills lend me very well for the lived role and needs of a head of school, but the vision of who that leader is and what they have done in their careers remains in an older paradigm of thought.
Despite my teaching experience, I’m not a “classroom teacher.” Despite my long and enduring commitment and work in DEI, I’m not considered an authority, and despite having extensive experience in all facets of school, I am not considered to have enough experience.
My assistant head of school and mentor has this knack for honing in on how I am doing and where my head is at. She’s been able to sense when I am open to feedback and when I just need a moment to vent. She has a superpower in this way. One of her leadership lessons is a lesson in patience and awareness.
Seeking the right moment and having the patience and awareness to recognize that moment. And picking those moments is equally an art. Be ready.