Transitioning to Headship by David Padilla

For 25 years, I’ve been telling my students the same thing: If I wanted you to write an English essay in one night, I would make it due tomorrow. Working for six hours the night before an essay is due is nothing like working one hour a night for six nights before the essay is due. When I accepted an appointment as head of school over a year before the actual starting date, I resolved to take my own advice:

Have a plan, start early, and pace myself in this race to the starting line.

The first step was to take inventory of all the networks and supports I have developed and which have shaped me over my time in independent schools. I knew I would need to leverage the lessons from friends and colleagues who had (sometimes unwittingly) been instructing me over the past quarter century. I reached out to those who had already transitioned to headship; I contacted accreditation chairs under whom I had served; I reconnected with undergrad and graduate school contacts whose opinions I valued; and I engaged my current head and other senior administrators in a series of Q&A sessions.

David Padilla has served as the head of upper school at Baylor School in Chattanooga, TN, since 2001. Prior to that, he taught English and coached soccer at St. Alban’s School in Washington, DC. He will become the head of Christ Church Episcopal School in Greenville, SC, on July 1, 2020.

In reaching out to those who had been a part of my journey thus far, I realized I needed deliberately to extend my connections by reaching out to those who would be part of my new networks as a head. These included leaders in professional organizations such as state and regional groups; executive directors of consortia or constituency groups of which my new school is a part; and heads at peer schools in the city, state, and region. I have made an effort to participate in workshops and webinars aimed specifically at newly-appointed heads and to explore working with an executive coach. Every step has been focused on relationship-building. At this stage, I have the freedom to weigh considerations raised in conversations with the understanding that any possible decisions or approaches remain in the “draft stage”; I have not reached the publishable or publish-ready stage of the process of transition. Thus, we’ve been afforded an incredible amount of freedom and transparency in our conversations.

I’ve also deliberately paid close attention to the school and community in which I will be serving. Beyond studying things as I had during the search process, I’ve tried to get at the heart of how things actually operate. This step expands the ring of influence and the scope of relationships that need my attention. Of all the those I could forge, none is more important than the relationships between the board (chair and members), direct reports (and key faculty and staff), community members, and me. So in methodical fashion, I continue to reach out directly to members of all these constituencies and to set up hour-long conversations with a simple premise: Tell me honestly what you see as the greatest challenges facing the school as well as the greatest strengths left untapped or under-leveraged.

These conversations are refreshingly agenda-free on my side; I am interested in listening actively to what each person has to say. I am intentional about telling folks that no one thing they say will control my opinions about this or that; instead, I am intent on gathering as many perspectives as I can and laying the groundwork for open communication.

While my efforts to build communication and knowledge have been time-intensive, they have not been particularly labor-intensive. The payoff, however, has already been considerable. With each conversation, my understanding of how people communicate, where their interests lie, and what makes them tick has expanded. Further, as that understanding has grown, I’ve both fleshed out my comprehension of the whole school environment and sharpened my focus on the broader community. The real challenge of this process has been balancing the duality of roles by continuing the hard work of my current responsibilities while simultaneously looking to the future of headship in a new environment. I remain keenly aware that there are competing interests here: I owe it to my current school and colleagues (i.e., the foundation for what got me here), as well as to my new school and colleagues, to not shortchange anyone.

In order to maintain this balance, I have also made it a point to prioritize self-care. One of the first things I did after being appointed was to seek out a counselor with whom I could work over the course of the year to make sure I was being deliberate about facing the challenges of staying centered and focused, navigating the change in roles and location, and — most importantly — assuring that I was not neglecting my loved ones. This last piece cannot be overlooked. For many of us, expanding leadership roles can take a toll on our spouses, kids, and close friends. It’s more than simply the hours we have to devote to meetings, school events, and crises which pull us away. It is also the fact that work in schools is heavily relational, so making sure we have enough emotional energy to be good partners, parents, and friends is key. It is this work which I hope will do the most to assure success going forward.

Less than a year ago, I would have had no reason to write this article. As I prepare formally to begin my role, however, I am struck by how having over a year to prepare has quickly become having only a year to prepare. Obviously, until I’m actually seated as the head, I won’t know if my preparation has been sufficient, but I do think that my experiences have been appropriately purposeful and intentional. While the steps I have taken and am taking to prepare are neither complete nor foolproof, perhaps they can provide ideas for others launching into a new phase of independent school leadership.

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