Two decades ago, few heads of school had any formal coaching. At best, when heads had challenges, they spoke with their spouses or friends or heads of other schools they knew well. Those heads who had a good relationship with the board chair might also confide with the board chair.

But times change.

The job of leading a school has become significantly more complex. The expectations are greater. Parents, anxious about their children’s experiences in school, scrutinize every choice a head makes. The pressures to establish a vision for a school, create a healthy, productive culture, and keep the school financially strong are ever present. In this era of educational change, heads are expected to keep the program on the forefront of educational practices. Add to this that heads are thrust into new positions in new schools with high expectations to initiate significant change immediately. Schools no longer can take a laissez faire approach to head support — especially in the first year of headship, or in the first year leading a new school.

Recently, we at Carney, Sandoe & Associates surveyed both new heads and experienced heads new to a school, asking them questions about their first year of headship. The responses tell us much about anticipating the challenges newly hired heads will encounter — and what we can do to support these leaders as they adapt to a new community and school culture and establish dynamic leadership for the school. More generally, the responses tell us what schools can do to support all heads so that both they and their institutions thrive.

I examine here new heads’ responses to two particular survey questions. The first focused on the three biggest challenges during the first year of headship, the second on elements of school-provided support that either were helpful or would have been helpful.

Challenges

Regarding the question of the greatest challenges of the first year of headship, the leading responses emphasized four areas of school life:

• dealing with budget and finances,
• working with the board,
• implementing changes, and
• acclimating to the school culture.

Money always is an issue, of course. Many of the heads surveyed noted the difficulties of dealing with a budget deficit, increasing fundraising for their schools, and otherwise managing the intricacies of overall budgetary matters. But some also felt that the school community did not understand the depth of the school’s financial difficulty or, worse, that the hiring committee had concealed the school’s fiscal challenges in the hiring process. Sometimes a school hires a head with the expectation that the new head will solve the school’s fiscal issues, especially with fundraising, but our survey makes clear that schools can be more disclosing about the challenges, which in turn would enable heads to establish a strategy for success.

Those surveyed also noted that conflicts frequently arise from either a lack of communication with the board or from a lack of board support. In many cases, the heads said that the board did not speak with one voice and that board roles were poorly defined. Some heads said they had to deal with particularly toxic board members or encourage an unengaged board chair to participate fully. Others noted the difficulty of managing board perceptions and expectations, especially a demanding agenda for change. In some cases, anxious boards desired to initiate a capital and endowment campaign before the head was ready. Heads often felt they needed to clarify boundaries so the board would stop trying to micromanage the head. In general, there was a shared wish for improved board governance, better board knowledge of best practices, and stronger and more consistent board leadership.

Implementing change, not surprisingly, was seen as a large and looming challenge. Heads noted the challenge of changing the school culture to enable institutional change. In particular, they noted the difficulty to create a strong administrative team that worked well with the head. This work involved encouraging administrators to become a unified team, rather than working alone, and embracing both the plan and process for change. The work also involved dealing with, or sometimes replacing, staff members who highly resisted proposed change or who otherwise did not support the desired plan.

Finally, heads noted the difficulty to adjust to and integrate into the new work environment and new school culture, and the personal challenge for the head and the head’s family to feel at home in a new locale. This category often is the greatest challenge for new heads. In many cases, there is a pronounced difference between the stated culture — the language in all the school documents about itself — and the actual lived culture. In all cases, the head must figure out these differences and get to know and build trust with the various constituents, particularly the faculty.

The Need for Greater Support

All heads of school go into the job well aware of possible difficulties. Even if they do not know or cannot anticipate every challenge and pitfall, they know the work will be demanding and that the school community will hold high expectation for success.

As a former long-time head of school (1998-2014) and a current certified executive coach, I am deeply aware of these challenges and difficulties and of the high expectations for the head. I have known many heads who rise to the challenges and thrive in their schools, and others who were unable to meet the challenges. Serving as a head of school can be challenging. It also is a highly rewarding and fulfilling job. But success also can be elusive. Very few heads can do the work well without some coordinated support. This is particularly true today because of the complexity of the work and the accelerated pace of change occurring in independent schools.

When asked about the elements of school-provided support in their transition that either were or would have been most helpful, many of the surveyed heads noted the following four essential categories:

• Open, productive communication with the board;
• Clear action items and performance reviews;
• A formal transition committee and clear transition process; and
• Executive coaching.

As noted above, one of the greatest challenges of being a new head or an experienced head new to a school is establishing a good working relationship with the board, especially the board chair. Lack of such a relationship in the first year often can lead to serious obstacles to success.

Survey participants overwhelmingly cited that having support from the board and a strong open line of communication with board members were integral to a successful transition. Some heads were glad to report that they had the needed support from the board. Especially valued was a supportive, committed executive committee and regular access to the board chair for continuing informal conversation. For others, negative interactions and regular disagreements with board members often led to frustration and institutional inaction. In short, a strong line of communication and a healthy atmosphere can make for a smooth transition.

Some heads said that more coaching for the board on its role — especially its role during a leadership transition — would have helped considerably. My experience confirms this. Board members, generally speaking, bring their professional expertise and willingness to serve a school they care about deeply; however, many board members have little experience on a nonprofit board, and even less experience on an independent school board.

Regarding the actual work with the board, survey participants cited a need for a clear set of goals and a timeline to guide their work as a newly appointed head. They also noted, in retrospect, that feedback and performance-based evaluations throughout the year would have provided a clearer understanding of their performance and board expectations. In particular, they encourage boards to set forth objectives between the hiring and the starting date; set clear first-year performance expectations; and develop a prioritized list of the top three action steps or concerns to address.

Survey participants also said that they benefited from — or would have benefited from — an appointed Transition Committee to plan and guide the leadership transition process. The work of this committee includes:

• supporting the new head, and possibly a family, in the transition to a new school and a new home in a new city;
• helping to introduce the new head to the school community — students, faculty, parents, alumnae, past parents, grandparents — and to the leaders of the community in which the school is located;
• communicating with the school community about first-year transition goals;
• helping the head acclimate to the school culture;
• serving as a sounding board for the new head; and
• providing informal feedback to help the head in the transition process.

One head noted that while he had a transition committee, it disbanded shortly after he started the job. The head wished it had remained intact through the first year or the first semester.

Executive Coach

Finally, the surveyed heads noted that outside help from an executive coach — both in the months before officially beginning the position and in the first year of headship — was a substantial help. Those who had a coach value the dedicated time. Those without a coach wished they had had one for both open discussions and for managing the difficult aspects of transition.

In my work as an executive coach with heads, my goal is to help every head of school understand and manage their many challenges so they can thrive in their work. To this end, my objective is to help new heads develop greater self-awareness — know themselves and their leadership styles better, especially their strengths and blind spots. I help them in the process of adjusting to change in their own professional and personal lives while leading change in their schools. I help them understand and deal with difficulties of life under the community microscope, especially how to manage conflict and work with the various constituents. I also serve as a professional and personal sounding board to help them manage the inevitable physical and emotional aspects of the work.

This is the sort of support an increasing number of heads crave and need as they strive to balance the many roles and responsibilities of being the head of school. Indeed, as my colleague Bill Clarkson points out, more and more boards of trustees, following the lead of boards in higher education and the corporate sector, are investing in coaching for heads and seeing the benefits firsthand.

The goal is for everyone to be successful in leading schools and for each leader to feel fulfilled in the work. When the various constituencies coordinate well, a new head has great professional satisfaction. In the past, we may have simply wished the new head of school good luck and given a pat on the back. Today, boards of trustees, hiring committees, and school leadership teams would be wise to understand the specific challenges new heads face and work together to offer a network of support that will lead to everyone’s success.

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Ann Teaff is an Executive Coaching Consultant with Carney, Sandoe & Associates. She began her career in education at University School of Nashville, first as a Middle School teacher of history and English, and then as an Upper School teacher of history, economics and political science. From there, she went to Garrison Forest School in Maryland, serving as Chair of the History Department, Head of Upper School, and Assistant Head of School. From 1998 to 2014, Ann was Head of School at Harpeth Hall School in Nashville. During this time, she ran two successful capital campaigns, increased enrollment significantly, founded the Online School for Girls, and established the Center for STEM Education for Girls. Ann currently serves as a board member of the Baltimore Leadership School for Young Women and St. Paul’s School for Girls.