Dare to Lead

Jamie Williamson

From The Compass Spring/Summer 2021

Those who know me also know my love of a good podcast. In particular, lately I’ve been engrossed with Brené Brown’s Dare to Lead podcast, based on her book, Dare to Lead: Brave Work. Tough Conversations. Whole Hearts. Her show has been resonating with me as I reflect upon the work our community is engaging in around diversity, equity, inclusion, and belonging: It is brave work, it embraces tough conversations, and it involves our whole hearts. I’m incredibly proud of our community in this moment as we come together in a spirit of mutual respect, teamwork, partnership, and collaboration. We’re working together to do something big and essential and critical to realizing our mission. 

From the outset, as Windward developed its Three-Year Plan for DEIB initiatives and tasked the new DivE In Committee to guide, advise, and oversee these efforts, it was critical for us to be invitational in the process. Our primary aim, guided by the School’s mission and vision, is to unite our community to problem solve for the greater good, bringing a collective voice that both honors and represents our diverse populations, life experiences, and viewpoints. As Maya Angelou said, “When we know better, we do better.” Because this work is so important, we’re driven to approach it from a multifaceted, methodical perspective. In partnering with DEIB expert Dr. Gene Batiste; in facilitating trainings at the trustee, leadership, and faculty/staff levels; and in inviting constituents from our community to engage in this topic, we’ve targeted measurable objectives that allow us to hold ourselves accountable. 

The importance of intention in this process cannot be overstated. While it can be tempting to respond reactively to ongoing events that highlight our society’s systemic injustices and inequities, choosing that path outside of a clearly defined set of values and goals can do more harm than good. We may feel surges of optimism when a problematic team mascot is replaced or when racist brand representations are eliminated; and while these actions are important, the real work we must do requires us to take our time and be intentional about what we do, what we don’t do, and when we do it. We’re listening to the voices at the table, and we’re making decisions based on the needs of our community. That, to me, is an incredibly hopeful place. This work is not about us telling people what they’re doing is broken or poorly intentioned; rather, it’s about us as a community saying here’s what we believe, here’s what our values are, here’s where we are, and here’s where we are going. And we will hold these commitments near and dear to our hearts and be accountable to them. I’m optimistic that this is a time when these conversations, while they’re not going to be easy, offer a real chance to engage in meaningful dialogue and effect positive change. 

We know that it’s not an option for us to choose not to engage in this work. Our values as a community require us to not only respect but also celebrate our differences. To embody our mission, to live our vision, we imagine a world where every child is able to overcome barriers and achieve unlimited success. The word every compels us to do so, and that ideal is what empowers us to dive in and dare to lead. 

Jamie Williamson
Head of School