New View EDU Episode 20: The Future of Schools as Desirable Workplaces

Available May 17

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We often focus on the student experience in our schools, which is a critical issue needing constant attention. But our school communities also include adults—the faculty and staff who work to make the student experience worthwhile. With the post-pandemic workforce shifting dramatically in all sectors, what can school leaders learn about transforming systems and practices to retain excellent teachers? How can we model leadership that supports and centers the well-being of faculty and staff? And how can we ensure that our schools are desirable workplaces where professionals can thrive and feel valued?

Clockwise from top left: Donna Orem, Crissy Caceres, Doreen Kelly, and Brett JacobsenDonna Orem joins host Tim Fish to moderate a panel discussion with three energetic, experienced heads of school: Crissy Cáceres from Brooklyn Friends School (NY); Brett Jacobsen from Mount Vernon School (GA); and Doreen Kelly of Ravenscroft School (NC). Together, the roundtable participants discuss new trends in workplaces nationwide, how they view their roles as leaders in recruiting and retaining excellent staff, and what’s next in developing supportive, compassionate, collaborative environments for every member of their communities.

At a time when both head of school turnover is at a record high and teachers nationwide are leaving the profession, there’s no doubt that something has to change. The school heads examine how clarity of mission, vision, and school culture contribute to creating desirable workplaces. Whether it’s modeling and uplifting community values like joy and personal agency, or making space for “work from your rest and rest from your work,” each guest agrees that independent schools must offer a real value proposition for workers in order to rise above current trends. Humility and curiosity also play a role; asking why teachers are leaving, what they need to feel supported in staying, and how schools have failed to prioritize well-being and balance are crucial to improving our workplaces.

Drawing on research, Donna, Brett, Crissy, and Doreen discuss the reasons teachers choose to work in independent schools, contrasted with the recognition of the deep struggles recently experienced by workers in the healthcare and education sectors. If we all agree that teachers are heroes in our schools, then why are they overwhelmed? What can school leaders and communities do to improve burden-sharing, listen more carefully to teacher concerns, and offer the very benefits—autonomy, fulfillment, respect, and work-life balance—that lead people to our schools in the first place?

Together, the three school heads step through different ways of thinking about their roles as supportive to their communities. Making space and time for each person to show up fully and authentically even amidst polarization and creating habits that allow workers to feel that they understand their purpose and are better for having been a part of that purpose are cornerstones of the practices they recommend for healthier and more desirable workplaces. 

In the spirit that there is always more to learn, each member of the panel offers suggestions for a summer reading, watching, and listening list, with books, podcasts, and documentaries as well as daily practices that might be helpful to other school leaders looking to transform their work. And each offers a personal vision of hope for the future of schools as places that will become more connected, more empathetic, more curious, more humble, and more rewarding.

Key Questions

Some of the key questions Tim and Donna explore with the school heads in this episode include:

  • Against the backdrop of the Great Resignation, what trends are occurring in independent schools around the stability of the workforce? What can be done about those trends?
  • How does school culture impact the way we implement supportive structures for teachers and staff members? How do our stated values and vision flow into our schools as workplaces?
  • In a time of increasing polarization, how can school leadership hold space for supporting all members of a community, from parents to teachers to students? What practices and habits can help?
  • What team-building practices might be particularly effective in providing balance and well-being for faculty and staff?

Episode Highlights

  • “I think it will force our industry to create great clarity around our why. We're not able to be all things to all people. And I think the clearer we are with our missions, we'll have great clarity about who chooses to work in our environment, who chooses to study in our environment.” (10:19)
  • “So rather than have an assumptive stance of what we believe to be true, I think that our leadership has to center ourselves with humility, to understand that we haven't had all of the right answers. And that perhaps, by the continuation of existing practices and systems, we have actually enabled a culture that hasn't optimized what healthy and whole existence in our schools look like. But our colleagues know the answers. And so I believe that this is a matter of connectivity. An honest reflection about not just what we've done well, but quite critically, what we have not.” (12:32)
  • “We say we honor the worth and integrity of every individual in a variety of phrases in our mission. And so this moment that we're facing now is about going beyond our aspiration and acting upon the very things that cause families to invest resources and time into partnering in the world of parenting with their children and our schools. And so it's time to face the commitment that we have made all along and consider the ways in which we have to rethink the way that we've acted upon those missions.” (27:35)
  • “The students are watching. All of the time. What a worthy call as leaders to care deeply about the people who…are truly at mission central, focused in on the kid. It is gifted work to be focused in on the people who are focusing on the kids as well.” (27:41)
  • “You don't rise to your goals. You fall to your systems, whether those systems be good or bad, you're going to fall to those systems. And so what systems are we falling to? And that part of that is how healthy is your team and how aligned is your team.” (31:09)
  • “Bridges have been essential to the modern world. They have helped define us. Bridges are connectors. They deal with proximity, where we become more proximate to each other because the bridge has been built. … What voices are we not hearing from? Bridges allow us to do that. And yet bridges have guard rails. Because they protect us. They help us make hopefully wiser decisions…we need more bridge builders.” (48:18)

Resource List

Full Transcript

About Our Guests

Crissy CáceresCrissy Cáceres is the current head of school at Brooklyn Friends School (NY). Crissy is a long-time friend to NAIS. She was a member of Call to Action, an NAIS think tank devoted to social justice efforts; she is a faculty member at the NAIS Diversity Leadership Institute; she co-chaired the People of Color Conference in Philadelphia; and she recently joined the NAIS board. Prior to joining the team at Brooklyn Friends, Crissy served as the assistant head of school at Georgetown Day School in Washington, DC. Throughout her career, Crissy has partnered with schools and organizations nationwide as consultant, presenter, and facilitator on various school leadership, social justice, and school culture and student engagement topics. At her core, Crissy embraces the values of a joyful, experiential, equitable, and comprehensive education for all. 

Doreen KellyDoreen Kelly leads the leadership team of Ravenscroft School (NC) and has been head of school since July 2003. She joined the Ravenscroft faculty in July 1999 as the director of the Lower School. Doreen is a Board Certified (BCC) Executive Leadership Coach and has served on the faculty at the NAIS Institute for New Heads. Prior to joining Ravenscroft, she had a 10-year career at Trinity-Pawling School (NY), an all-boys boarding/day school where she served as upper school director of studies, head of middle school, English teacher, and volleyball coach. Before that, she taught English as a Second Language for two years in France. She graduated from the University of Pennsylvania with a bachelor's degree in English and a master's degree in education. She also studied for two years at Villanova University, where she also played Division I volleyball.

Brett JacobsenDr. Brett Jacobsen is CEO and head of school at Mount Vernon School (GA). As a current marketplace leader and CEO with 25+ years of experience, Brett has been able to collaboratively transform organizations through assembling high-performing teams, generating innovative ideas, and building exceptional brands while partnering with Fortune 500 and 1000 companies. During his tenure at Mount Vernon, the school has experienced growth of more than 60 percent and now serves more than 1,200 students. The school is currently building a global campus through the launch of an online high school, MV Online. Additionally, Mount Vernon also has a significant research and strategy consulting arm of the school known as MV Ventures. Recognizing the heavy lifting of the team around him, Brett had the opportunity to be honored as the Most Admired CEO in 2017 by Atlanta Business Chronicle, and he served as a proud member of the Leadership Atlanta Class of 2013. Additionally, Brett is an R&D founder, board member, podcaster, and national and international presenter.