In March, at the annual conference of the National Association of Independent Schools (NAIS) in Atlanta, I will join three other school heads on a panel that we have - only half jokingly - titled “Why the hell would you want this job?”  We’ll tell our very different, unvarnished stories about leadership to help attendees better understand the rewards and challenges of headship.

I’ve been thinking about this panel. What is hardest about my job and what’s most rewarding? My takeaway: the crucibles of leadership are the reward.

I’m as human as the next person, so when people tell me I’ve disappointed them, or when they criticize my decisions, actions or inaction, I feel the accelerated heart rate, stomach butterflies and sleepless nights that anyone feels when criticized. While it’s easy to feel and project confidence (and to sleep soundly) when others express support, it’s just as easy to feel unsettled, ungrounded and isolated when others criticize. 

In nearly sixteen years as Head of St. Luke’s, I can recall many times (some very recent), when people have been angry, frustrated, and/or disappointed with me. It’s terribly uncomfortable, but I’ve learned to reframe my discomfort as opportunity. If I can lean in, and invite those who disagree with me to do the same, the benefits—trust, relief, understanding, respect—overwhelm any differences we might have.

I’ve found that listening to the personal stories of people with strong opinions has often opened my eyes and brought me perspectives I had not fully considered.  Talking in person rather than engaging in email debates enables an emphasis on commonalities and shared goodwill. As a colleague said recently, “When we think of it as a debate, we already have our jerseys on.”  Leaving my jersey in the locker room has enabled me to listen with empathy and compassion rather than approaching conversations as contests to win.

Oliver Wendell Holmes famously wrote:  “Certitude leads to violence.”  I agree with Holmes.  The capacity to consider differing opinions, to hold conflicting views in each hand while evolving in understanding and judgment, separates leadership from dictatorship, constructive dialogue from angry, fruitless shouting matches.  

I want our students, who are emerging leaders, to see the opportunity in disagreement, and I try to model it for them.  That makes leadership, at its heart, a human endeavor, beset by ambiguity and contradictions while offering the most rewarding opportunities for learning and impact.






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