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The Smartest Person in the Room

I value humility in a leader. As an independent school search consultant, I associate humility with learning, and being a learner is one of the key qualities of effective leadership. Leaders are curious. Leaders probe, look for insights, and value the opinions of others. Thus, a candidate referred to as the “smartest person in the room” is not someone I normally pursue for a headship. That application usually goes in the “no way” pile.

But lately, under certain circumstances, I have seen the value of being the “smartest person in the room.” Let me explain by describing a composite of schools I have encountered over the last six years. 

XYZ Academy has just hired a new head who started four months ago. The school has been struggling with enrollment since the 2008 financial crisis and during that time has had two heads of school not including the new one. The school has lost 150 students in the last ten years. The loss of students has impacted many facets of the school’s operation, most notably teacher salaries, class size, and the athletic program. Trustees have a myriad of theories about why enrollment has not bounced back: 1) tuition is too high, 2) football team is weak, 3) school is not getting the “word” out, 4) admissions director is ineffective, and more. Many trustees are exasperated as they have been espousing their respective theories for years. Each one knows something is wrong, and each one supposedly knows how to fix it. They just need a head who “gets it.” Most of the trustees are parents. 

Enter the fictional Frank Smith, the new head of school, hired to solve the enrollment problem. Here is the reality behind the enrollment crisis Frank faces: 

     1. The balance of power is clearly with the board of trustees as is the case with many leadership transitions in independent schools.

     2. The board consists of mostly parents; thus, the trustees’ judgement about the long-term sustainability of the school is clouded by the experience of their children—both positive and negative.

     3. Trustee theories about the low enrollment are, at best, superficial and certainly not supported by data, much less a sophisticated interpretation of data.  

In essence, Frank has a board with too much power, shaky judgment, and little knowledge of how to effectively address the enrollment challenge—not a group of people that should engender confidence in developing an effective plan. Add to this scenario the real possibility that Frank is a first-time head who came up through the academic ranks with little knowledge of working with a board.  

Despite what you might think, Frank’s first task is not to come up with a plan to address the enrollment decline. Rather, it is to re-balance the power between administration and board while achieving some degree of consensus about the nature of the problem. In short, Frank needs to earn power by demonstrating to the trustees that he is the “smartest person in the room,” at least when it comes to understanding the real challenges the school is facing. This is a necessary prelude to getting the power brokers on the same page. Moving forward without a clear consensus about the nature of the real problem is a prescription for constant re-litigation. Quagmire wins. 

In order to be the convincing expert, Frank must study the school, its history, its competition, as well as current and recent data. He must understand parent perspectives, faculty perspectives, and the drivers and barriers associated with behavior in the market. Interviews with key stakeholders as well as interested parties outside the school community, analysis and interpretation of data, and frameworks for interpreting the meaning of these findings are all part of the “roll up your sleeves” work ethic of the new head. Frank needs to present his findings to the board, demonstrating that he has done his homework and speaks with a degree of authority. In doing so, he forces the board to think strategically, to ground decisions in data instead of the experiences of their children, and most importantly, to make the head a full partner, if not the leader, in devising strategies for addressing the enrollment challenges.  

New heads are often told that in the first year, they should develop relationships with key stakeholders, especially the trustees, administrators, and faculty. This is sage advice, but often new heads also need to systematically understand the school and its challenges at a deeper level. That knowledge needs to be shared with trustees and teachers in a clear and compelling presentation that stokes confidence in their leadership.  

Please note: I do not recommend that new heads constantly prove that they are the smartest people in the room, but on occasion, it’s necessary for them to demonstrate their expertise in order to establish a healthier balance of power with the board, create a foundation for real change and help schools get unstuck.  


1. As a new head, you need to quickly assess the balance of power between the board and the administration. If this balance is skewed toward the board, and it’s clear that there is little expertise supporting trustee perceptions, one of your early goals is to redress that imbalance.

2. The best way to redress the imbalance is to become an expert on the school, eventually making a compelling case for your understanding of the real challenges.

3. In order to become the expert, you must do your homework. Delve into the history and culture of the school; uncover the primary narratives that enhance or inhibit creative thinking; and study data and demonstrate a sophisticated understanding of what it means. In short, prove to the board you are the “smartest person in the room,” at least for that moment.

4. Achieve a consensus within the board and ideally, within the faculty and administration, about the true nature of the challenge. This consensus must be understood and accepted by these stakeholder groups in order to avoid the re-litigation trap.

5. Once consensus is achieved, articulate a vision that not only inspires stakeholders but if achieved, addresses the challenges you have articulated. This step is harder than you might think because it often touches the school’s identity in the marketplace and thus, raises yet again the personal interests of the trustees as well as parents. Be prepared to put on your bullet-proof vest. 

6. When you present your vision, suggest probable (but not set-in-stone) strategic initiatives that the board should begin to think about so that trustees can see the enormity and complexity of the challenge and the time it will take to achieve the vision. Trustees also need a glimpse into their roles in undertaking this monumental endeavor.

7. Throughout the process, identify opinion influencers and win them over.

8. As you move into implementation, relinquish power to those who clearly know more than you do. Amassing power is not the end game. In fact, you should always defer to those who know what they are talking about. In this way, expertise, not the mere fact that a person is a trustee or a head of school, becomes the determining factor in identifying the right power brokers for addressing the topic at hand. If those people are not on your board, then start recruiting them.

9. Finally, despite the inevitable setbacks along the way, do not look back. Yes, you may have to calibrate change, but you must “keep your eyes on the prize.”

10. Enjoy the journey!