Six Truths About Leadership

The past few years have been cruel to schools. A lethal, unpredictable pandemic, accompanied by a racial reckoning, enmeshed in a toxic political climate, has challenged school leaders in ways they never anticipated or prepared for. But although the situation has been wholly new, in many ways brutally so, it has illustrated the importance of several timeless truths about leadership.
In our consulting work with schools, my colleague Michael Thompson and I have met with more than 350 groups of heads, administrators, teachers, trustees, and parents at dozens of schools since spring 2020. We’ve asked heads and administrators what lessons they’ve learned and worked to troubleshoot issues they were facing, and found the keys to coping have been simple. Simple not as in easy, but as in fundamental, basic. These six lessons, among others, will remain essential to school leadership in this year ahead.
1. Don’t mistake dilemmas for problems.
A problem has a solution; you fix it. A dilemma is built into a situation; you cope with it. I learned this distinction from Matthew King, former head of The Rashi School (MA), with whom I worked over the years. Dilemmas are not within your power to resolve. You’re not helpless; you cope. But you can’t bring the issue to full closure. The distinction here is about expectations. When we read something as a problem, we expect to solve it. If our solution doesn’t last, we assume we’ve failed. When we read something as a dilemma, we expect to take constructive action but are not surprised when we have to revisit it.
The pandemic posed multiple dilemmas. Particularly in the first year, heads of school, despite having no public health training, repeatedly had to make rapid decisions about matters with life-or-death implications while conflicting public health mandates proliferated. And no matter how careful a school’s COVID precautions, the virus spread in their communities, illustrating a dilemma schools have always faced: the limitations of their reach vis à vis that of parents.
Learning to read COVID’s challenges as dilemmas instead of problems proved helpful to heads. Making the distinction doesn’t make leadership easy, but it can reduce leaders’ guilt and self-recrimination and sustain their energy and perseverance.
2. Learn to live with leadership’s built-in dilemmas.
Many challenges for school leaders are external. Others are internal and chief among them is a set of tensions that are inherent in leadership. One is managing versus leading. “Managers do things right; leaders do the right thing,” as the well-known organizational development saying goes. Leadership is mission, vision, strategy, transformation. Management is details, minutiae, schedules, and supplies––and it has consumed school leaders’ these past few years. An elementary principal told me he spent the 2020–2021 school year “like a wedding planner. I was all details: ordering PPE, escorting students to the cafeteria in small groups, contact tracing. Zero instructional leadership.” Leadership is a higher-order activity than management, but no school can succeed if it is not well-managed, as this principal recognized when he added, “It’s not what I signed up for, but it was what my school needed.”
Another inherent tension is that leaders become a parental transference object. The term refers to the universal tendency to project onto authority figures dynamics that characterized childhood relationships with parents. A faculty member’s relationship with its leader is largely rational and professional, but never purely so. We all want someone we can look up to and trust. Depending on our history, we may be inclined to idolize a leader, fear him, or mistrust his intentions. A crisis kindles transference. When schools reopened for in-person instruction, some faculty members who were scared about the shift reacted to their heads of school as though they were a bad parent who didn’t care about their safety; others were readily comforted by their reassurance.
Closely related to the parental transference tension is another tension, which I call “isolation in a fishbowl”: The leader is at once very public but very alone. It truly is lonely at the top, but the person at the top is frequently in the public eye and always seen as “in role.” Heads are always the head of school; they must always be “on.” This can provide moments of pleasure and a sense of authority, but is a burden. As one head shared, “I’m widely known but not personally known. Even pre-COVID, I was rarely able to just be me. Ever since COVID, that’s been even more true.”
I can’t foresee any future in which school leaders will be free of these built-in dilemmas.
3. Bite off what you can chew.
“Man plans, and God laughs” is a Yiddish proverb that administrators should heed. School leaders chronically over-aspire. Leading a school, is, like life, marked by events that are unplanned and, often, unplannable. A pandemic is, of course, an extreme instance. But no leader survives a year without having important objectives intruded upon or displaced by the unexpected. Yet I’ve rarely seen a school head’s goal list that acknowledges this. The functions and outcomes expected of schools have mushroomed, reflected in bloated strategic plans and lengthy mission statements that pledge far more than any school can deliver. However well-intentioned, the more promises a school makes, the more goals for the head. And a given year’s goals routinely include tasks that will become permanent parts of the job. They won’t appear on the ensuing years’ lists but will still require effort. As these accumulate, the head’s job balloons.
If COVID has taught us nothing else, it should be that, once drafted, every leader’s list of goals should have at least a few of its targets replaced with blank spaces labeled “unplannable.”
4. Shape the meaning.
We imagine that we react directly to events, but we actually react to what they mean to us. To most educators and parents, COVID protocols primarily meant “safety.” To others, they meant “infringement on liberty.” Meaning depends on many factors, including the event itself, the context in which it occurs, our unique personalities and life histories, our culture, and so on. When leaders make a policy or announce a change, they can’t dictate its meaning, but they can help shape it––by spelling out its why, what, and how. Of these, the first is the most important, especially when the decision will be a challenge for people. Keith Shahan, former longtime head of the John Burroughs School (MO), once told me, “Good leaders develop a narrative for the school, so that people understand where they have been, where they are, what they need to do to get where they need to go. [They link] the school’s values to the narrative and communicate it well.”
Telling the school’s story is a key way heads shape meaning and inspire followership. During the pandemic, many faculty members complained about “toxic positivity,” which one teacher defined as, “administrators keep saying we’re doing great, but they don’t want to hear how exhausted and scared we are.” Rah-rah boosting, even if well-intended, rings hollow. Michael Thompson and I saw repeatedly that morale improved when heads acknowledged teachers’ distress (“I heard you loud and clear that you’re tired and that it’s so hard not to be able to connect with students the way you want to”). Doing this allowed heads to then thank teachers in a way that had a real impact and help them reframe their expectations in light not just of their wishes but of the realities they were facing.
The pandemic underscored that leaders are ideally placed to define what constitutes real achievement. Doing so can nourish people’s spirits and effort even in the face of unprecedented difficulty.
5. Be clear about focus and process.
When heads overpromise, they become harder for people to follow, and they themselves typically fail to follow through on their multiple initiatives. This saps faculty energy and breeds frustration and cynicism. A school is always a more engaged, purposeful place when the head is clear about focus and process. Focus means specifying which few goals matter most right now. COVID disrupted all sorts of plans and projects, but it demanded focus. To shepherd their schools, heads needed to clarify “this is where we need to concentrate now, and here’s what that means for each of us.”
The corollary to clarity of focus is clarity of process, spelling out which decisions are whose. Too many administrators, even when certain of the need for a particular course of action, fear seeming “top-down.” They broach their idea indirectly, hoping faculty will reach the same conclusion. This comes across as insincere and damages trust. Teachers want to know: Are they asking us or telling us?
In this regard, I think of a head who drew effusive faculty praise for, as one teacher said, “being calm and caring throughout—and for being straight with us all the way.” As it always has, being clear about focus and process earned him credibility and built followership, even during—especially during—the worst of the pandemic.
6. Get help.
A head of school is the ultimate source of support for faculty, staff, students, and parents. Directly or indirectly, all can turn to them. They, however, can only turn to the board chair, to fellow heads, or to a coach or consultant. The heavier the leadership burden, the greater the need for support. But many heads are reluctant to seem vulnerable or needy. These past two years, when trustees have asked, “How can we help you,” too often the reply has been, “I’m fine,” even when the head has definitely not been fine.
I recently talked with several groups of heads whose schools are located near each other and have long competed for students but who found tremendous support in being candid with one another about their COVID-related challenges.
These past two years have reminded us that “help” means not just “advice,” but “sharing the burden.” And that leaders do much better when they’re less lonely.
The pandemic’s impact may linger for a long time. But the “lessons” it has reemphasized have long been cornerstones of successful school leadership. I don’t mean to suggest that we should be grateful to COVID for reminding us of truths about leadership. But they bring a practical perspective to leading, combining opportunities leaders can seize with realities they must acknowledge. The outlook for schools remains full of unplannables they can’t control. More than ever, we will need leaders who can sustain high aspirations for themselves and their schools, but who can also accept—and help their schools accept—truths they must live with.
Rob Evans
Rob Evans

Rob Evans is a psychologist and consultant to schools. His most recent book, co-written with Michael Thompson and published by NAIS, is Hopes and Fears: Working with Today’s Independent School Parents.


Renee DuChainey-Farkes
8/10/2022 11:22:32 AM
Hi Rob, Great and timely. Yes Heads need to stop saying "I'm fine" and find mentors to "just provide support and a listening ear." I'm working with two schools in this capacity and the mentor role helps keep them on track as they've been pulled off track for two + years. Thanks for the article. I hope a lot of people take it to heart!

Michelle Morrison
8/10/2022 10:46:14 AM
Thank you for these wise words! Your book with Michael Thompson, 'Hopes and Fears: Working with today's independent school parents' was a lifeline during the tumultuous days of pandemic and cultural upheaval this past year.

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