The Art of Second Guessing

I spoke recently about the value and importance of trust in the relationship between the head of school and the board chair. One aspect of where trust breaks down is this idea that hard questions posed by members of the board of trustees are code for such members to adopt the demeanor of second-guessing anything that they simply don’t agree with. Second-guessing has become an art form among some trustees who believe they must be heard and who believe that they are doing their due diligence when asking what they think are legitimate questions.

To be sure, the need for dialogue is critical. The need for questions is not only legitimate but a factor that often demonstrates a healthy culture for the school’s board. But too often, a line is crossed when certain trustees exhibit behavior that suggests they no longer trust leadership and have moved into a pattern of questioning everything to be sure everyone knows they are the one asking the tough questions. It can become disrespectful to the process and demonstrates a lack of support for the head of school, the board chair, and even other board members. When calling out such behavior, the trustee claims to be asking the hard questions because someone has to play that role.

There is often a link between second-guessing and a personally biased agenda against some aspect of the school for which the trustee feels compelled to be the authority. What is the harm? It diminishes unity – the belief that we are all in this together, that we have a shared vision for the future of the school, and erodes the relationship between head and trustees. What is the answer? It’s found in the process of selecting, training, and providing continuing education for the board. There is never a substitute for enlightened leadership! Why does any of this matter? It is because the stakes are high as independent and faith-based schools are preparing leaders with knowledge, character, and a desire to impact the world in positive and meaningful ways.

My philosophy of the board’s role is one that is grounded in best practices. It means staying focused on the core responsibilities of the mission, strategic direction, fiscal oversight, and the hiring and supporting the head of school. Of course, such responsibilities can and should be more broadly interpreted to adjust to particular circumstances. The global pandemic is an unfortunate ideal example of where the trustees and head must clearly demonstrate a new level of trust, support, and encouragement of each other’s roles.

I occasionally hear from trustees at different schools who believe it is their responsibility to become “immersed” in the work of the board and therefore take their role so seriously that they have lost or compromised their perspective of where their focus should actually be. My response is to lighten up, understand your role, be willing to learn, accept the fact there is strength in unity, and that the future of the school does not necessarily depend on what you think! This sentiment is not meant to be critical but rather a recognition of what is genuinely important, meaningful, and strategic.

Uncertainty is the new normal. In an environment that is constantly changing, consistent, unwavering belief in best practices, shared vision, and support for leadership is the most welcome path forward. Let’s work together to get it right. The stakes are too high to do otherwise.

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