Leadership Lessons: Won’t You Stay Just a Little Bit Longer?

Spring 2024

By Robert Kosasky, Amy McNamer

This article appeared as "Staying Power" in the Spring 2024 issue of Independent School.

You now have the ultimate job security—just not necessarily in your current institution.” That’s what Pat Bassett, former NAIS president, told participants at the 2002 Institute for New Heads. Robert Kosasky, a nervous 34-year-old in his first month of headship, remembers it well. He had just moved with his young family to Potomac, Maryland, where he and his wife didn’t know a soul. He’d heard warnings that most people in this role don’t make it past five years, or their third board chair, or even their first controversial decision. We haven’t unpacked our boxes, Robert thought, and already I’m hearing about getting fired?

Today, Robert is still the head at St. Andrew’s Episcopal School. While his 22-year headship has been a generational and growth-filled journey, he remembers the anxiety of the early years all too well. Heads today are facing an even harder first chapter of headship, as issues of distrust, polarization, health and well-being, and workforce turnover stress communities and their leaders. According to NAIS research, the median head tenure has fallen to five years. Meanwhile, as the pace of head retirements continues to grow and most schools look to hire experienced heads, newer heads quickly have tempting opportunities for fresh starts and greener pastures. As the executive director of the Association of Independent Schools of Greater Washington, a regional association of 78 schools, Amy McNamer has seen 30 heads come and go in the past five years.

But what if newer heads didn’t jump schools so quickly? What if more heads in their first five to 10 years would consider the benefits of staying at their schools? In the right environment, a generational headship can be deeply fulfilling—even transformative—for the head and the community. Staying at one school, through waves of opportunities and challenge, can lead to deeper personal and institutional trust, relationships, and growth. As Robert can attest, life really does get better for veteran heads, and here’s why.

Years 1–5: It’s Not You, It’s Headship

The first five years are objectively the hardest, regardless of a head’s preparation and competency. Before your first day on the job, you are the vessel for the community’s hopes, prayers, fears, and hurts. You are the new kid in town and also the boss. You are likely balancing a mandate for change from the board (collectively your employer and individually your most important supporters) while simultaneously being told that you should take time and first hear the community’s stories.

You don’t know the players and their motivations. You’ve inherited staff members who know and understand the school better than you do, and now you need to figure out whose advice to follow, how to build a coherent team, and what decisions to make or defer. The chief financial officer—who reports to you and expects you to fluently read the balance sheet—also implements your contract. Meanwhile, you are discovering inexplicably unresolved “issues” at the school, and now you get to guide a swift yet graceful cleanup process. You’re responsible for the institution’s well-being as well as the care of every individual in the community. And by your first Thanksgiving break, you’ve internalized that you have a job in which many of your new-head peers won’t last.

By year two or three, you also see some progress. You at least know the calendar cycle and ritual events. You get to know the board and colleagues and slowly understand what each person contributes and how to work together. Listening to faculty, staff, and families, you begin to hear themes and understand where to put their energy. You can begin to build your leadership team and culture, one conversation or one hire at a time. The glass-mostly-empty trustee rolls off the board, and the challenging family’s youngest child eventually graduates. The colleagues who really loved the other finalist decide that you probably won’t wreck the school after all. Your spouse and children settle in. You survive your first crisis and gain the community’s trust in the process. This all takes enormous effort, but you begin to see the institutional return on investment.

Years 6–10: Return on Investment

You’ve done the work and are starting to enjoy the majority of planned and impromptu interactions with your community. On the tough days, you know how restorative 15 minutes reading in a kindergarten classroom can be.

The board becomes a source of support, and, in turn, you are increasingly comfortable sharing what really keeps you up at night.

From experience, you understand the difference between a crisis and a manageable problem. And for the crisis, you have trusted advisers and legal counsel on your contact list. Insecurity and uncertainty about how to do the job have greatly subsided.

As an experienced and proven leader, you are likely fielding an increasing number of calls from search consultants. While some of these opportunities might sound tempting, you should be thinking about the exciting capital campaign you still want to complete or the transformative program or vision you want to make a reality at your current school. Remember that newness has its costs everywhere, and time remains on your side.

The Second Decade: What Kind of Headship Do You Really Want?

Over the past decade, Volatility, Uncertainty, Complexity, and Ambiguity (VUCA) has become a favorite phrase of educational thinkers. VUCA creates churn and churn kills progress. So shouldn’t leaders be living examples that VUCA isn’t inevitable? And as a long-term leader, don’t you want and deserve a little less VUCA in your life?

In the second decade of headship, you will have had time to fix or replace the broken or toxic cultural elements (or occasionally just wait them out), and the community won’t waste nearly as much time and energy debating and overreacting to the “small stuff.” Heads with longevity are a known quantity—with strengths and challenges, priorities and preferences, and, most of all, supportiveness, trustworthiness, and vision. You’ve accumulated deep relational capital, perspective, and far more freedom to choose how to lead your school. Under a longer headship tenure, schools begin to feel a sense of security and confidence that attracts deeper talent and support. Aspirations unfold.

Board meetings now start to feel warm and generative. You can tell colleagues that you trust and support them completely, because you do. Donors make “stretch gifts” because they believe in your integrity, vision, and long-term love for the school. You can also counsel newer heads about their anxieties and dilemmas, reassuring them that “it will get better.” You can see their own initiatives through from start to finish. These are golden years of headship, filled with meaning and possibility.

The Third Decade: From Generation to Generation

According to NAIS research, fewer than 4% of NAIS heads make it to their 20th year in the same headship. This is unfortunate. By this point, you’ve left a visible imprint on the school—a more broadly diverse student body and faculty, distinctive signature programs, multiple capital campaigns, new buildings or other expansion, a heightened institutional pride and public profile, and a distinctive and appealing culture of trust and aspiration. You have a genuine fondness for faculty, staff, and board members and consider many as more than just “work friends.” You’ve hired or invited onto the board several former students who hold the school’s history and recent progress equally dear. You stay connected to many other alumni through shared institutional love and stories.

When you speak of the school’s history and future, your own story is intrinsically intertwined. In this stage of headship, the next phase of leadership for the school and its larger educational community will be the primary motivator. In an era of increasing turnover and centripetal forces, how can you help your school plan for succession and attract and retain the next, more diverse great generation of faculty, staff, and trustees? As institutional trust declines in the nation as a whole, how can schools be a countercultural web of connection and vocation? How can you help your school thrive long after you leave and contribute to educational thinking beyond your own campus?

This pitch for long-term headship might not appeal to everyone, and many head-school matches are made far from heaven. But we hope more leaders will consider this generational opportunity in a world that too often equates career advancement and satisfaction with restless movement. If you want to build something lasting, look down at the grass where you are. How green could it become?

Read More

There’s much to be said for staying at one school, and we’ve published articles about it before. Check out these and other articles at nais.org.
"Valuing the Profound Power of Continuity in Headship,” by Dan Glass, Independent School magazine, Summer 2022
Looking at Lengthy Head of School Tenure,” by Danny O’Brien, Independent School magazine, Summer 2022
Teacher Perspective: Recognizing the Value of Staying at Your School,” by Kirsten Lindberg, Independent Ideas blog, November 2022

Robert Kosasky

Robert Kosasky is head of school at St. Andrew’s Episcopal School in Potomac, Maryland.

Amy McNamer

Amy McNamer is executive director of the Association of Independent Schools of Greater Washington.