What not to ask your head of school
Boards often wonder what their head of school is thinking. “What keeps you awake at night?” is a question I hear boards asking their heads. At the center of that question is genuine curiosity and, with well-functioning boards, a genuine desire to be helpful.
How that question lands, and how the head responds, depends greatly on the health of the board-head relationship.
Just under the surface, the head might be pondering:
I am worried that we won’t hit our enrollment targets for next year.
What if our health insurance rates will increase more than the 15% we budgeted for?
I fear we miscalculated our ability to pay that balloon payment.
Dig a bit deeper, and the head is thinking:
Parents aren’t giving my new kindergarten teacher enough of a chance to be as good as I know he can be.
We made changes in our math program – teachers love it and parents hate it. What if in a few years we realize we shouldn’t have made the change?
Our annual fund is doing worse than last year. I know why, but that comes across as defensive.
If they could say what they hold more deeply, you’d hear:
I made a mistake in hiring our CFO.
I feel so much pressure and am working all the time. I not sure I can sustain this.
I am not sure I can tell you what I am really thinking.
Am I going to get fired?
Here’s the catch. In reality, the board may only want to know what the head is thinking just below the surface. These thoughts are uncomfortable and complicated, but they are also manageable.
Dig deeper, and thoughts become complex, without easy answers.
Deeper yet, and the thoughts bring into question the level of trust and quality of communication among the head, the board chair, the executive committee, and the board.
Creating the conditions for high-trust between the board and the head requires a shared commitment. It requires a practice of leaning into difficult conversations. It requires time.
Don’t lead with, “What keeps you awake at night?
Begin with creating a space, a culture, in which all members share a commitment to learning and honest dialogue. Consider asking:
How do we set the tone for our meetings? How are all participants “invited to the table” in ways that establish boundaries, emotional safety, and confidentiality?
What are our boundaries or norms that, when crossed, tend to shut down trust and dialogue?
How do we invite perspective-taking and manage disagreement?
What are our strategies for reflection?
It takes time for mutual trust to grow. Only then can you say, “I would sincerely like to understand what is on your mind.”