Learning from Difficult Conversations

Fall 2013

By Michael Riera

Editor’s Note: The following is an excerpt from Making the Most of Difficult Conversations, by Michael Riera, published by NAIS, 2013. The book is available through the NAIS website.

William Deresiewicz said it well, especially for school heads, in “On Solitude and Leadership,” in Independent School magazine (Winter 2011): “It seems to me that solitude is the very essence of leadership. The position of the leader is ultimately an intensely solitary, even intensely lonely one. However many people you may consult, you are the one who has to make the hard decisions. And at such moments, all you really have is yourself.”

Being a leader is a lonely business and requires the ability to make tough decisions. And with this responsibility comes the requirement that we each continue to grow as learners, and not just so that we model this attitude and practice for colleagues, students, and families. It is so that we can handle, as well as possible, the important decisions we must make on a regular basis involving the health of our schools. In this sense, for many school heads, professional and personal development are one and the same.

Indeed, the actual decisions and how we carry them out are equally important. That is, a good decision implemented poorly does little for the institution in the long run, and we have all been there. Whether it was changing an academic program, the dismissal or promotion of a faculty member, or a discipline decision that was either too public or too private. Granted, never will we, or should we, strive to please 100 percent of our constituencies 100 percent of the time. (One of my former board chairs, Joe Di Prisco, told me early in my career: “If you’re doing your job, you are going to periodically piss off a bunch of people. Just make sure it is a different group each time.”) Our challenge is to consistently make the best decisions for our schools and to carry them out in the best possible ways.

Independent school leadership requires us to both stay in the loop of the constant email and chatter inherent to all of our schools and to simultaneously cultivate the practice of silence that Deresiewicz alludes to at the beginning of this chapter. That practice of silence will in specifics be different for each of us, but in essence pretty much the same. It requires creating a regular opportunity for reflection, whether it is through prayer, exercise, music, meditation, or an art. We need to make this a priority. Or as Paul Chapman, the former head of school at Head-Royce School (California), said at a new heads conference: “My one piece of advice is to exercise first thing in the morning. Otherwise, your day will get booked, and you’ll never get to it. Make your health a priority.” Rob Evans offers a variation of this when he urges school heads to create a Friday evening ritual. He suggests an expensive bottle of cognac from which you pour a single drink and reflect upon your week. He likes it to be expensive so that the experience is special. And obviously, it does not have to be cognac or even alcoholic.

The popular spiritual leader Deepak Chopra speaks eloquently on the need for a practice of silence: “I place so much importance on this idea of silence. I’m not saying everybody should do it, but even if you took five or 10 minutes of quiet time every day or every other day or once a week….” he commented in the Los Angeles Times (December 26, 2010). ”Ask yourself simple questions like, who am I? What do I want? What is my life’s purpose? Is there a contribution I can make to my community or to society? What kind of relationships do I want to have? What is my idea of well-being, and how can I achieve it?”

Whatever your practice, make sure it is a time when you can hold anxious ideas in your mind and heart. Let them bounce around and make you uncomfortable. Explore the discomfort. Is it your natural empathy? Is it part of your idealism that every student can be made whole again within your school? Is it doubt about what you are planning to do? Is it an insight into a pattern of your leadership that is important and painful to recognize?

My experience is that, if we are willing to see patterns in how we handle difficult conversations and decisions, we are then able, with courage, to make changes to those patterns when they are ineffective or there are better ways. Say you have a tendency to take something personally and get defensive when having a conversation with a parent, colleague, or student. Changing this pattern requires time, patience, and persistence –– and this happens in three distinct stages:

  • In the first stage, we notice we have gotten defensive and taken comments personally after we have made a tough decision or had a difficult conversation. At times, this happens days later upon reflection; at other times, it occurs just moments afterwards. But in both cases, it is too late to do anything about it.
  • In the second stage, we recognize our patterned behavior as it happens, but we are unable to change our responses. (This happens to most of us as parents interacting with our children, especially when they are teenagers.) We know what to do, but we are unable to stop ourselves and do it.
  • In the final stage, we liberate ourselves by recognizing the emergence of the pattern. We notice it before acting out and are therefore able to make a conscious decision to behave in a different, more productive way. We know we have a choice, and we exercise it.

Just as we need to continue to grow and develop intellectually through our careers, we need to do the same emotionally in our roles as school leaders. And this only happens if we make this kind of growth intentional.

One of the richest sources of your professional development in this regard are your colleagues in the independent school world. But again, it takes intention and initiative to tap those resources. For example, at conferences, it is typical for school leaders to gather informally –– often over a few drinks –– to connect and engage with one another. That opportunity is often wasted, however, as many of us do no more than swap stories. Instead, the next time you are in one of these situations, consider the words of the poet e.e. cummings: “Always the beautiful answer who asks a more beautiful question.”

Be as bold with your colleagues in the topics you raise and questions you ask: How do you manage your anxiety in your more difficult conversations with the people at your school? How do you give negative feedback such that the other person has the best chance of hearing what you are saying and improving? How do you evaluate your performance in some of these tough situations –– what are your criteria? Clearly, none of these questions have easy or pat answers. In fact, each is a conversation unto itself. And when we can do this with ourselves and other school leaders, we will automatically have more of these same kinds of conversations back at our schools.

Finally, we have all read about –– and in many cases, experienced –– how the job of head of school has gotten too large for any one person to manage, let alone learn how to be in two places at once. CEO…lead teacher…lead fund-raiser…one-person public relations department…top human relations professional…chief story teller…visionary….it all seems like too much for any one person. And it is, and it isn’t. Quite simply, what distinguishes effective leaders is their presence at any given moment. No head of school can be everywhere. What really counts is being truly present wherever you are.

So, in the end, the key to leadership is not just showing up, it is showing up and being present. Ultimately, it is about learning to be present during some of the toughest moments, conversations, and decisions we face as leaders in independent schools. The better we are able to do that, the better we are able to lead our schools.

Michael Riera

Michael Riera, head of school at the Brentwood School (California), is also a best-selling author, award-winning columnist, educator, television commentator, and national speaker on issues of children, adolescents, families, and parenting. He is co-author with Joe Di Prisco, of Right From Wrong: Instilling a Sense of Integrity in Our Children (2002), Field Guide to the American Teenager (2000), Uncommon Sense For Parents With Teenagers (1995), and Surviving High School (1997). His most recent book, Staying Connected To Your Teenager, was launched with three appearances on Oprah!