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A pair of superintendents share self-reflections about decision-making support for neophytes and experienced school system leaders alike

鈥淵ou don鈥檛 have to swing at every pitch.鈥�

This was the advice given to Andrew by his superintendent nearly three decades ago when he was a young, green and apparently brash high school principal. The superintendent had asked him to stop by his office at the conclusion of a school district leadership team meeting, where he provided Andrew with some constructive feedback that would result in better relationships with school leaders at other levels of the organization.

鈥淓xcuse me?鈥� Andrew replied.

鈥淵ou need to let some of their suggestions go by without sharing why it would be such a bad idea for the high school,鈥� the superintendent said. 鈥淵ou just crush their ideas, and you don鈥檛 really endear yourself to them, so when you need their support on something down the road, you鈥檙e less likely to get it.鈥�

Thirty years later, Andrew still admits he鈥檚 probably not the most reserved of colleagues, but that lesson has remained with him, and it pops into his head every now and then when he hears a suggestion or comment that causes a visceral reaction. It reminds him to step back, demonstrate restraint and allow the conversation to flow without his added criticism.

Typically, the group moves beyond any bad ideas without his input and, therefore, without harming any relationships that are at the heart of effective school improvement efforts. At other times, those ideas evolve and become projects he can support or contribute to positively, which also fosters collegiality and shared decision making.

Informal Support

Unbeknownst to Andrew at the time, he was receiving a bit of informal coaching that was meaningful and memorable. It increased his self-awareness and ability to reflect, leading to better relationships with colleagues and serving as a turning point in his approach to collaboration.

While informal coaching has been beneficial for school leaders in a variety of settings over the past few decades, 鈥渃oaching in education remains a relatively underexplored phenomenon,鈥� according to J.A. Moynihan, writing in 2025 in the journal Irish Educational Studies. This is likely true for several reasons:

Many school leaders aren鈥檛 convinced of the need for coaching;

School budgets have not typically included support for coaching contracts;

The pool of effective coaches for school leaders is shallow; and

The field of education is historically reticent to spend money on services not deemed 鈥渆ssential鈥� because funds are always scarce.

While executive coaching would clearly benefit the neophyte school leader, we argue that all leaders can benefit from skilled coaching, regardless of how long they鈥檝e been on the job. We have yet to meet a school leader, including ourselves, who has it all figured out. Working with a trusted coach who can point out those moments when we should 鈥渓et a few go by鈥� or when we should step courageously into the breach can transform our work and bump our leadership to the next level.

A Difficult Call

Deep into Maria鈥檚 tenure as superintendent, she was struggling over a personnel issue and needed an objective thought partner. She was losing sleep, avoiding the colleague and working double time to do half of his work. She was trying to figure out whether to retain a director-level employee or let him go, and it was eating her up.

The person had been in a difficult-to-fill role for two years and demonstrated competence at times, but was untrustworthy, unable to meet critical deadlines and was a difficult colleague for many in the organization.

Maria was torn 鈥� there were a lot of red flags, but the risks of change were high. Maria鈥檚 frustrations and fears were paralyzing her. She called her coach.

鈥淲hat is holding you back from cutting your losses?鈥� her coach asked.

鈥淚鈥檓 afraid of what happens in the interim and if I can鈥檛 fill the position,鈥� Maria admitted.

鈥淎nd what鈥檚 happening now, with things as they are?鈥�

Maria paused. 鈥淚鈥檓 spending 10 hours a week managing the fallout from missed deadlines and not getting what I need.鈥�

After two sessions with the coach, Maria made the difficult call to let the director go. Because she鈥檇 mapped out the ripple effects with her coach, she was prepared. She had a transition plan ready, had identified interim coverage and communicated the change with confidence rather than apology.

Within weeks, Maria noticed she鈥檇 reclaimed the time and energy she鈥檇 been spending managing the fallout from this situation. Six months later, with a stronger hire in place, the entire department was functioning more smoothly. More importantly, Maria now had a framework she returned to whenever paralysis crept in: What鈥檚 this costing me? Is that cost worth it? The coaching hadn鈥檛 just solved one problem 鈥� it had given her a tool she still uses today.

Lending Sustenance

The main role of a coach is leadership development. In an increasingly polarized and shifting environment, education leadership has become a nearly impossible job. To succeed, education leaders need to realize what leaders in the private sector, professional athletes and others have known for a long time: Having an objective sounding board, an accountability partner and structured, rigorous reflection supports leadership development.

Due to the constantly expanding workload, the role of an education leader, whether principal or superintendent, has become less appealing and less tenable, leading to serious issues not only with recruitment and retention, but also with school quality and improvement. If school and district leaders come and go like revolving doors, there is a lack of a consistent vision, stalled change implementation and increased staff despondency. A coach can help sustain the leadership work that is essential to successful schools.

Coaching sustains leadership by building capacity to manage stress, think systemically, enhance self-awareness and refine communication skills. With coaches by their sides, both of us became more confident, capable leaders. Maria gained skills to think through complex issues, while Andrew learned how to strategically temper his voice. Both served their districts for over a decade, more than twice the average tenure, making a lasting difference in their school communities.

Superintendents and principals face unique isolation. Their most complex work is confidential, leaving few insiders to consult. They work in a deeply human-centered profession where stakeholders bring considerable personal investment and emotion. Lawyers handle legal questions but can鈥檛 offer strategic guidance. A seasoned leader who has been in the trenches 鈥� but isn鈥檛 mired in community emotions 鈥� provides invaluable support for the loneliness and complexity of the role.

Coaches help leaders anticipate stakeholder reactions to cutting programs, teams or positions. They clarify the values underlying decisions about employee retention, budgets and new initiatives. The cost of missteps is enormous. The benefits of supporting the top leader are immense.

Identifying Benefits

Researchers are paying greater attention to the benefits of coaching for school leaders in an effort to provide support for the impactful work being done.

In an article about executive coaching for K12 Digest, Toby Travis, a school headmaster in Buffalo, N.Y., says outside consultants can assist school leaders in many ways: 鈥済reater self-awareness, skill enhancement, personal and professional goal setting and action planning, feedback and reflection, insights to manage conflicts within the school, strategic decision-making, reduction of stress, professional accountability, and the list goes on.鈥�

Educational leadership coaches also engage school leaders 鈥渋n purposeful growth conversations that will positively impact collaborative decision making, teacher leadership behaviors and classroom practice,鈥� says Beth Ray, writing in 2017 for School Leadership Review.

Targeted support can be especially effective when it is context-informed and human-centered, according to Ciaran Collins, Regina Murphy and Martin Brown of the Institute of Education at Dublin City University, writing in 2025 for Frontiers.

Forward Movement

Conventional coaching wisdom says industry experience doesn鈥檛 matter. We disagree. Given the unique challenges education leaders face, we believe field experience significantly strengthens the coaching relationship. This is especially true at times when a client needs a thought partner.

The superintendency, in particular, is a lonely, isolated job, and few others understand the complexity of factors involved in decision-making. A coach鈥檚 experience in the trenches can add insight to reflection questions that can illuminate the path for a client.

In education, as in life, change is the one constant. Leaders who seek school improvement and want their schools to stay relevant inevitably will negotiate challenging situations when trying to bring about that change. Having a coach not only models vulnerability, self-reflection and a willingness to grow but also can instill the confidence and courage to continue moving forward on behalf of students.

Coaching offers an excellent and proven solution to help propel education forward in these complex and challenging times. 

Maria Libby, who retired as superintendent in July, is founder of Libby Education Partners in Camden, Maine. Andrew Dolloff, who retired as superintendent in July, is assistant professor of educational leadership at University of Southern Maine in Portland, Maine, and author of Leading with Intent (Bloomsbury, 2026).