10/23/2018 by Bill Clarkson |

Executive Coaching for Independent School Leaders

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A Case Study

Jeff, a first-time Head of School, was several months into his third year as Head at St. Arden’s Day School (SADS) in a suburb of a large city. This established, co-ed, K-12, day school (founded in 1955) enrolls 950 students, employs 150 FTE faculty, and has 28 members of the board of trustees. It sits on a bucolic 130 acres with a stream running through it.

SADS has some history connecting it to Anglican traditions, but over time has become more identified as a school committed to the spiritual and character development of students, but without a denominational identity. While most enrolled students are from self-identified Christian families, the chapel program is interdenominational and interfaith in focus.

The Chair of the Board in place when Jeff was hired (also the chair of the search committee that resulted in Jeff’s selection) has retired, and Jeff is now working with the new Chair, a 45-year-old real estate CEO and graduate of the school, who is serving in his eighth year on the Board but first time as Chair.

Jeff’s first year was mostly a honeymoon period in which he did a lot of listening, getting to know people and the culture of the school. The Board had been excited about his appointment, but had not done much planning by way of transition and onboarding. It only provided him with the general charge of getting to know the school, identifying the major issues that he and the Board thought necessary to address, determining changes that could be made to propel SADS into a more successful and stable school, and constructing a 360-degree Head-of-School performance evaluation in order to model a much-needed performance evaluation instrument for faculty and staff.

That first year was a steep learning curve for Jeff, and while he identified several issues that needed addressing and ultimately required significant change initiatives, he made no big moves and kept his focus on forming relationships. In his second year, several of these issues began to scream out for solution, and Jeff’s end-of-the-year evaluation indicated frustration on the part of parents, faculty, and the Board. They felt that Jeff was not being proactive enough.

Among the immediate and complicated issues Jeff faced were the following:

1. He had inherited an administrative team that had a history of not working particularly well together. The Assistant Head had actually applied for the headship position, but had been rejected in the final round of the search. Jeff felt no degree of loyalty or support from this individual. In addition, the other leadership team members were in the habit of working independently in their own siloes.

2. The faculty included 7 to 10 veterans, each with 30-plus years of experience, who clearly had slowed down and were considered by many colleagues and parents as dead weight. Even so, they were deeply connected to the SADS community and, for the most part, liked by everyone.

3. The school had a successful sports program over the years, though recently, several teams in the major sports were underperforming. Many parents of players in those sports, a group that included some trustees, either wanted the coaches replaced or the athletic director fired.

4. Student drug and alcohol abuse had become a problem. Most parents of students who breach school rules were more defensive and protective of their children than positively cooperative with the school in holding students accountable. Indeed, the whole issue of student discipline had become a battleground. At the same time, the school had not yet developed a program to address the students’ overall health and wellness.

At the end of Jeff’s second year, he and the Board were in clear agreement that these issues needed immediate and thoughtful attention, and that changes should come soon. However, not all Board members were on the same page with respect to the solutions. Jeff’s energized, gung-ho Board Chair was most energized about the potential initiatives to resolve these matters.

Then Jeff’s third year began. The opening Chapel service to welcome new students and faculty into the community featured readings from the Hebrew Scriptures, the Christian New Testament, and the Koran. The music was magnificent, and the whole tone of the service was celebratory and inclusive of the rich religious diversity of the community. Yet a very vocal host of Christian parents exploded with anger and demanded an explanation for how a “traditional Christian school” could allow readings from “apostate faiths” in this beloved chapel. Letters, emails, Twitter posts, and phone calls of protest began pouring in to the Head’s office and to trustees.

Challenging Times

Not all independent school leaders face this particular set of challenges. But these challenges are, in many ways, typical for Heads leading independent schools today.  Simply put, independent schools are far more complicated than they once were. At the same time, the expectations of all constituencies have risen considerably. These expectations, combined with broader cultural changes, the changing nature of education, and the overall rising pressure for schools to compete for families and students, have put immense pressure on Heads of School to lead their school communities through what amounts to a process of constant change and growth.

The issues at SADS — both the collection of issues identified by the Head and Board as those needing thoughtful solutions and the sudden new challenge about the religious identity of the school — touch on particularly tough contemporary questions. In the push for greater diversity in the school — a move that most educators believe is important for moral, academic, and societal reasons — how does a school appeal to and work with its traditional base, especially when that tradition arises from a single religion and represents a strong donor base? In an era when parents feel more like consumers buying a product and hope their children can have the strongest transcripts possible for admission into elite universities, how does a school institute a discipline policy that is fair and keeping with the school’s values? In a school that prides itself on being a close-knit community that supports its faculty, how does one deal with aging teachers who can’t carry their weight or, for that matter, ask longtime independent teachers to agree to evaluations after years of working without them? In the area of athletics, how intensely should one focus on winning? Does a school really need to dedicate itself to dominant teams every year? When institutional change is clearly needed, how does one work with a leadership team that is used to working independently and that doesn’t share a sense of urgency?

These and many other issues and responsibilities are part and parcel of what independent school leaders face today. Other topical leadership challenges that I see include:

  • Implementing best practices in governance at both the Board and administrative level.
  • Improving HR operations and meeting the growing number of legal requirements for nonprofit schools.
  • Managing and relating to multiple constituencies.
  • Creating financial stability and affordability while retaining or improving quality in all dimensions of school life.
  • Leading the process for campus master planning and strategic planning — especially regarding optimal educational space configuration, educational programs, and program delivery with financial projections.
  • Overseeing fundraising and capital campaigns, and balancing this out with the growing need for financial assistance among families.
  • Improving communication across all sectors of the school, but especially from the Head of School to all constituents (verbal, written, and time sequencing).

The bottom line is that, taken together, these kinds of pressures are too much for a Head of School, no matter how talented, to handle alone. They are particularly hard when the pressures for change mount and come in waves — which is often the case with newly appointed Heads these days.

Given all this, it’s not surprising that more Heads of School — as with college presidents and other organizational leaders — are turning to executive coaches, not to solve problems for them, but to help them see situations from numerous perspectives, develop confidence in decision-making, improve one’s self-awareness and identify leadership strengths, and move their institutions forward.

The Case for Coaching

A year ago, my colleague, Stephen Kennedy, retired Head of School, wrote an article for Independent School entitled, “Lonely at the Top.” In it, he argued that, with the aforementioned challenges and opportunities, the Head of School often finds him or herself in the loneliest of positions — having to make large institutional decisions under a searing spotlight. Given what is at stake and the isolation of the Head in making these decisions, there is a real need for objective, totally confidential, trusted coaching, mentoring, and counseling support, whether that individual be in the first, second, third, or whatever year.

In my own work, I am hearing from clients (Heads of Schools — some in their first year, some experienced and newly appointed) that the demands and challenges are increasingly perplexing and sometimes overwhelming. Even with experience, many Heads admit having little to no control over developing situations. They also say how wonderful it is to have a professional sounding board such as an executive coach.

For their part, the healthiest Boards of Trustees, and especially Board chairs, recognize the realities facing the leaders of their schools, and willingly invest in executive coaching. This is increasingly the case for all Heads, regardless of the stage of their career, but it is particularly true for new Heads, whether experienced or not. From the beginning of a Head’s new start, there are so many perils lurking that can cause one to stumble. An effective coaching experience not only can help the Head navigate these challenges to a successful conclusion, but also possibly extend the average tenure of an individual’s leadership of a school. No thoughtful Board wants to see metastasizing dysfunction and a truncated tenure.

As Kennedy points out in his article, when a Head of School finds an executive coach who is a good match, the results are rewarding for both the Head and the school. About his own experiences working with a coach, Kennedy writes, “… the payoff was exceptional. I benefited personally and professionally, as did those who worked with me.”

Kennedy goes on to outline the essential value of an executive coach for Heads — helping Heads develop stronger and more fulfilling relationships with constituents, greater personal and professional effectiveness, a better work-life balance, enhanced emotional intelligence, and awareness of one’s blind spots.

You’ll notice that he does not say anything about finding solutions to specific problems. In my experience, Heads aren’t looking to others to find solutions. Rather, they need someone outside their respective institutions, someone objective, to help them figure out how to solve the problem. In this regard, just having a sounding board can help tremendously. When that sounding board is someone deeply familiar with the challenges of school leadership, it’s even better.

But a good executive coach serves as more than just a sounding board. When I talk about the value of executive coaching, I focus on how coaching can help Heads learn and develop skills and greater self-awareness — and how, with these improved skills, Heads can help transform their institutions for the better.

Among the skills coaching can help Heads improve are:

  • Their SELF-AWARENESS and understanding of strengths;
  • Their effective and inspirational LEADERSHIP;
  • Their ability to manage transformational CHANGE;
  • Their ability to successfully manage CONFLICT;
  • Their ability to establish a top-functioning TEAM; and
  • Their ability to find BALANCE in their lives.

When one has honed these skills, one can offer exceptional institutional leadership, especially when it comes to institutional change.

The Higher Education Model

Leaders at the corporate level are turning to executive coaches in greater numbers — and by all reports are seeing positive results. The same is true at the collegiate level. An article in Trusteeship Magazine, “Meeting the Leadership Challenges: Why the Most Effective Presidents and Chairs Seek Coaches,” makes it clear that college presidents are increasingly turning to coaches and finding the experience valuable. In fact, an executive coach is now often included in the onboarding process for many new college presidents — even those who come with experience at other colleges and universities.

I suppose it helps to know that CEOs are turning to coaches in greater numbers, but because schools Heads have more in common with college presidents than with corporate CEOs, or for that matter with public school principals, this is a good place to turn for lessons.

While coaching can be valuable at any stage in one’s career, it’s particularly valuable at the start of one’s tenure at a school or university. In my experience, new Heads, as with new college presidents, are in a precarious situation — no matter how enthusiastic the school community is about the new appointment. It’s not just that expectations are high, and thus difficult to meet. For the Head, it’s also about getting to know the school culture quickly, developing new professional relationships, connecting with key constituents, and even helping one’s family and self adjust to a new location — all before one can tackle major issues.

But the first year isn’t the only time when coaching is valuable. In the Trusteeship article, Terrence MacTaggart, former chancellor at the Minnesota State University System and the University of Maine System, points out that there are four key periods in one’s tenure in which coaching can help:

  • when the president gets the job and before starting;
  • the first 100 days of the presidency;
  • the broad middle period, which could extend for years, where the major dynamics are periodic problems or challenges that come up with the board, faculty, staff, enrollment, or team building; and
  • the exit phase, when the president is thinking of departure, or others are thinking of it for him or her.

I would add to the list the times when one is tackling new challenges for a school — say, a first major capital campaign or dealing with a difficult faculty situation or addressing the need for a paradigm shift in a school’s focus (adding a new division or even altering the school’s mission). Because it is critical to meet these leadership challenges well, it is crucial to get the clearest perspective on the challenges and have a sounding board for ideas on how to move forward.

In another higher education article, “Can Deans Fix Higher Education Dysfunction?” the authors included executive coaching as one of the successful strategies for universities needing to deal with a host of challenges, including budgeting woes and faculty upheaval. “Perhaps the most effective component of the program,” the authors note, “was the regular one-on-one coaching that the deans received to aid them in managing particular problems.”

An executive-coaching pilot study by the National Association of Independent Schools (NAIS) supports the value of coaching. The most positive outcome of the study was, on the one hand, the encouragement and validation Heads received from their coaches and, on the other hand, the outside perspective the coaches could offer. In particular, Heads in the study reported that this outside perspective was most useful in thinking through crisis situations in the first year. In turn, Heads reported that the combination of affirmation and the outside perspective gained from the coach gave them courage to make and implement difficult decisions.

In short, most of the Heads reported that the coaching experience was very positive — especially in helping them develop greater self-awareness and perspective. Perhaps equally as valuable, the Heads in the study reported better relationships with the Boards and Board chairs.

Coaching is not a panacea. If a school is clearly heading in the wrong direction or if a Head of School wants to use a coach to force through an agenda that is not supported by the community, a coach cannot help. But in my experience, in the vast majority of cases, a coach can help a Head of School — and Board chairs and other school leaders — be both more effective in their work and happier about their work.  Stephen Kennedy’s article, “Lonely at the Top?” hits the proverbial nail on the head. Coaching not only helps Heads feel less isolated in the decision-making process, it helps them build closer connections with their school communities. In doing so, they become more effective leaders.

The Case Study Redux

Many, if not most, Heads of School can identify with one or more of the leadership challenges Jeff faces at St. Arden’s Day School.

What’s important to know is that Jeff is a strong, thoughtful, and personable leader who understands the complicated dynamics in leading a school. He is capable of making difficult management and operational decisions. He has some skills in addressing “change dynamics” and is deeply committed to the concepts of best governing practice in his partnership with the Board. He is, in other words, the right person for the job. Nevertheless, he does feel isolated and recognizes the exhaustion with the work as he experiences the roller coaster ride of discouragement and encouragement. And now he has to make major decisions in a timely and thoughtful manner.

I will leave it up to Heads of School and Board chairs reading this to decide whether Jeff would be better off pushing forward on his own or if an executive coach with experience in independent education would be the better option for both Jeff and the school.


Bill Clarkson, a former Head of School with more than 30 years of experience, is an Executive Coaching Practice Leader with Carney, Sandoe & Associates. An Episcopal priest, Bill has also worked in parish ministry and pastoral counseling.

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