Leadership, ego, talent, learn, headship, identifying, management, team, collective, characteristics, confidence, quality, initiative, dumbest, guy, room, in


“My goal is to be the dumbest guy in this room, and I’m pretty smart,” said a successful C.E.O. to his senior administrative team. This C.E.O., a good friend of mine who started and sold two successful businesses, was recounting this story to me recently. At first it seemed an odd statement. Shouldn’t the C.E.O. be the smartest person in the room? Shouldn’t the leader have all the answers, know what to do, and when to do it?

I couldn’t stop thinking about his statement and how it relates to other leadership positions – like a Head of School. It illuminates our preconceptions of leadership that are outdated and dangerous, and yet, they persist and their pernicious impact prevents schools from tapping the latent talent and wisdom within the community.

So what’s behind this successful C.E.O.’s statement? What are the assumptions about leadership and what lessons might a Head of School learn?

The first assumption is an unwavering commitment to talent. The Head of School might be the smartest person in the room, but with the absence of talent around her, the school will flounder or, at the very least, fail to reach its potential. Talent touches the quality of everything a school does. Without it, the fulfillment of a vision and the implementation of a strategic plan are doomed. Identifying, cultivating and most importantly, utilizing talent are hallmarks of any successful headship.

The second assumption is a belief in the collective wisdom of a group. Good management is, in part, about using conversation and collaboration to frame the right questions to find the best answers. One Head of School often told his senior administrative team, “The best idea wins.” It makes no difference where great ideas come from; what matters is that they are great. True great idealeaders know this, and they create the conditions that encourage talented players to have a strong voice in the team’s deliberations. Research is very clear that “teams consistently outperform individuals” when it comes to making accurate predictions (Walter Frick).

The third assumption is that learning never stops. When the C.E.O. makes it clear that she can learn from senior administrators, that in fact she expects to learn from them, she is unleashing the most powerful tool any organization has – the creativity of its employees. And yet rarely is this leadership quality talked about in search committee meetings. One consultant actually suggested to a search committee that “being a learner” should be close to the top of the characteristics of an ideal Head of School. Not one member of the committee voted to incorporate it in the criteria used to evaluate candidates. Learners do not care from whom they learn. They just want to gain deeper and deeper insights into the landscape of reality in order to optimize the school’s efforts. Introducing new information, challenging assumptions, reframing issues, analyzing data, recognizing biases – these are all critical in making good decisions. They are examples of real learning. And they lie dormant when Heads of School lack the self-confidence to be wrong. Being a “learner-leader” emanates from a sense of humility and curiosity, as well as a strong desire to win.

Humility is not just an inherently attractive human quality; in a leader it sets the stage for success. Humility incorporates the previous assumptions – the belief that the talent of others is critical to success, the power of the group, and the importance of listening and learning. In addition, the humility of the leader signals to followers to bring their most thoughtful and imaginative selves to the table. It encourages strong voice and initiative. It allows followers to “keep their eyes on the prize” instead of on the enhancement of the leader’s ego: “We’re not playing political games; we’re focused on winning.”

Independent schools are facing serious challenges today. Successfully facing these challenges will require great leadership, leadership that doesn’t focus the spotlight on the leader, but rather on helping the school do a better job of living its mission. Independent schools need Heads of School like my friend, Heads who see the critical importance of harnessing their egos and letting others take center stage in order to achieve something great. So, Heads of School, make it your goal to be the “dumbest guy in the room.”