Why Getting Comfortable in the Unknown is Key to Leadership

Spring 2018

By Terry Macaluso

On a surface level, leadership can be seen as the activity of causing something to happen through exertion of influence that provokes others to take action. In this line of reasoning, we might say that we know what leadership is. Based on experience, however, I’d define leadership a little differently: It’s less about knowing than it is about being comfortable not knowing.
To lead is to live with ambiguity, to embrace complexity. With all due respect to mission, vision, and values, we lead people. Simultaneously, we coexist in a state of future anticipation that cannot be predicted but for which we claim (or are expected) to be preparing our students. I suggest that leading for today—without trying to anticipate what might be—is enough. Such anticipation is driving us to search for the next, new “it” thing that will launch the next, new “it” acronym, thus driving our budgets and our boards to the breaking point. In this way, we continue to fuel the race toward . . . what?
To be comfortable not knowing—to embrace complexity and live with ambiguity in the present—is a gift a leader can give his or her community. Steady presence, confident guidance, constant and prudent improvement in an atmosphere in which children grow up and faculty and staff continue to develop professionally—as well as personally: This is leadership in a school.

The Cultural Aspect of Leadership

Every day, thousands of children and adolescents arrive on our campuses, and, for the most part, they find their way into classrooms, laboratories, studios, and other learning spaces without prompting. Hundreds of adults arrive on those same campuses ready to interact with students and with each other, again, without direction.
There is a structure in place that guides everyone on a daily basis. No active leadership is required for this process. Routines have already been established. (This is not to suggest that leadership was unnecessary in the creation of those routines, but once set, the logistics tend to take care of themselves.)
But the manner in which those activities are carried out, the attitude with which individuals approach their projects, the ways in which individuals interact indicates leadership—and all of that is indicative of a school’s culture. The culture is the evidence of leadership in an organization.
The cultures we build and sustain in independent schools are complexity incarnate. Culture is the result of leadership the way bread is the result of flour, yeast, and water; the right ingredients combined in the right proportions. Scores of ingredients compose independent school leadership. We’ve all seen the lists, which so often include integrity, authenticity, humor, empathy, fairness, and compassion. The culture of the school reflects the degree to which those ingredients are “mixed” by the school’s leaders. What’s interesting is that different people can include all the same ingredients, with varying results. Too much empathy and the hard conversations don’t happen. Too much fairness and decisions can’t be made.

The Complexity of Our Schools

To be a leader—in any organization—is to embrace complexity. In an independent school, there are multiple
complexities to embrace.
  • „First, our schools serve many constituencies, each of whom sees the school from a slightly different perspective, and each has different expectations.
  • „Second, individuals within constituencies differ in their individual perspectives and expectations.
  • „Third, our communities extend to multiple generations; as time and distance separate us, recollections vary and reality shifts.
  • „Fourth, populations change, while missions try not to.
  • „Fifth, cognitive science continues to teach us how learning happens—and it’s not the same for everyone; a good teacher for this student might not be for that one.
  • „Finally, our schools are designed for children and adolescents, but they are inhabited by an adult population who goes to work—not to school—every day.
Leadership in an independent school is the ability to shape this complex community—a workplace—made up of children, adolescents, and adults. Ages 5 to 75 all work together; this is unique to schools.
And in a school, or any mission-driven organization, the workplace is the objective. More so than in many typical American workplaces—a grocery store, a consulting firm, a law office, a health club, or a car dealership—in which there are specific task-driven targets. In schools, we are influencing the thinking and the social and emotional development of young people. Our behavior, attitudes, and habits of mind, and the degree to which we are prepared to do what we do, create the culture in which children and adolescents either do or do not flourish. It’s on display every day. It’s slightly different every day. It’s influenced by variables that are completely unpredictable, and it’s the leader’s job to sustain a consistently positive, supportive, engaging, intellectually stimulating, emotionally caring, and socially inclusive community every day.
That has to be done by working with any number of people who arrive on campus from private lives in which any number of things may be going on. Trust must be established. High, though achievable, expectations must be expressed. People between the ages of 5 and 75 have to figure out how to spend meaningful time together in an intermittent conversation that goes on over the course of months and years. Teaching is never finished. It’s the most exhilarating work there is, but teachers don’t get to turn it off. The way teachers feel about one another and about the work they do matters as much as any skill or ability they bring to their work.
Sometimes when leaders try to get someone else to do something, they have to enable, coax, guide, inspire, induce, inveigle, or influence the other to do it. But motivating a car salesman or inspiring a paralegal to do a better job than last time involves interactions, task execution, results, and feedback that all take place within a community of adults—a community in which it is presumed that each is responsible for oneself.

In a school, it’s different. Our students are watching us interact. Our students are benefiting—or not—from the quality of the relationships shared among colleagues. The leader’s job is to expect and sustain a culture that
demands positive, constructive relationships among adults.

Recognizing Leadership

Occasionally, I have a chance to work with faculty members from institutions other than my own, usually as part of a leadership search. One question I often ask when I meet with other groups of faculty is: How would you know if you were well led? We might all consider that question regarding many domains of our lives; it’s tough to answer.
Leadership is ineffable. We think we know what it is, but we struggle to recognize it in all its forms. It’s present in the way it feels to walk onto a campus. It’s present in the conversations you hear among students and faculty. It lies in the ability of a leader—maybe it’s the head or the board chair or the academic dean or the middle school head—to live with ambiguity.
Leadership occurs when somebody has learned when to take a stand and when to let it go. When somebody knows how to explain to a teacher why “it’s not working.” When somebody is aware of the network of relationships from which every individual arrives at school every day and in which each participates as well. When somebody understands human development well enough to allow students and adults the space they need to become their best selves. And when somebody knows when boundaries have been transgressed. Those recognitions are leadership in action.
Leadership in a school involves the community of adults agreeing to perpetuate a community of trust among themselves. Everyone—faculty, school leadership, staff, and parents—must agree to live as colleagues in a way that demands much more than competence; it requires a willingness to transcend petty politics, to ignore the demands of ego, and to trust that the intentions of colleagues are positive.
The leader in a school must demand that this adult culture be perpetuated if a school is to do its best for students; and the adult culture must insist that its leader be prepared to accept such a responsibility.
Terry Macaluso

Terry Macaluso is head of school at Eastside Preparatory School in Kirkland, Washington.