Story Number One
Early in my administrative career, the school was struggling with a weak French program. We decided to bring in a foreign language expert to spend several days examining the program, sitting in on classes, and talking to students. At the end of the last day, she gave me several action items and I, in turn, gave her a check. On her way out, she said, “You can take those actions I just gave you, or you can hire someone who knows what she’s doing.” 

Story Number Two

I once asked one of the most prominent executives in the insurance industry why he was so successful. His response: “I know the business.” 

Story Number Three

I was on a lengthy phone call with a board chair whose school was a client. At one point I talked about the enrollment decline and the failure of the school to successfully address this issue. The chair assured me that the board talks about enrollment at every meeting, but “I don’t know that I or any other trustee is qualified to talk intelligently about how to fix the school’s enrollment problem.“ I responded, “Yes, given my ignorance about the business you run, it would be ridiculous for me to tell you how to solve your company’s problems.” 

So, what do these stories have to do with my skepticism (not dismissal) of boards operating in the generative mode—a concept that encourages boards to focus on framing strategic issues that lead to greater insight and better decisions?

When I heard a presentation on the concept of generative boards years ago, I could not help but be excited. “Of course, let’s have lively discussions about big strategic issues. Let’s involve trustees in framing the major issues and figure out the right questions to ask. Besides, who wants to sit through the typical boring trustee meeting with committee reports?” Moreover, the concept of a generative board fit well with my vision of what a great classroom looks like—lots of participation and engagement. Shared leadership that encompasses a diversity of opinions and provides a meaningful experience for trustees sounded appealing. I was smitten.  

As it turned out, I never suggested it to any of my board chairs, not then or later. I’m glad I didn’t. Here’s why:

1. For the most part trustees don’t understand the school business, and there is no reason that they should. I know the “generative mode” apologists argue that deep knowledge of context is often unnecessary for many “big picture” discussions, and I realize that framing an issue is not the same as establishing a strategic direction. But initiating the framing exercise is best left to the head of school because of her deep understanding of the complexity of the operation, the school’s capabilities, and the political landscape. Not all of this knowledge can efficiently be revealed to trustees whose very different experiences may prevent them from comprehending the nuances of leading a school. For example, many trustees fail to grasp that teachers are not merely employees; they are stakeholders, and they can have power. How much time does a head want to spend at a trustee meeting explaining this reality to a set of trustees who manage their companies in a different way? In short, the generative mode strikes me as naïve, inefficient, and incredibly difficult to execute. 

2. I know trustees are supposed to be objective and not let their other roles (can you say parent?) interfere with their judgment about what is best for the school. But often this is not the case. Trustees are human beings, subject to bias just as we all are. It’s fanciful to think that given a blank tablet, and in the absence of a deep knowledge about schools or any kind of research, that these trustees (often parents or alumni) will not quickly gravitate to their own preconceptions and biases once unleashed with the freedom of generative thinking. “How competitive should our athletic program be?” can quickly turn into “Why don’t we have a better lacrosse program?”

3. Generative board meetings diminish the power of the head of school; even the advocates for generative boards admit this. When Ms. Major Donor advocates strongly for a particular strategic direction, and she has support from a few other major donors, how is the head supposed to react, no matter how dumb the idea is? Even the ardent supporters of generative boards have to admit there is an imbalance of power between administration and board. And what about trustee dynamics outside the board room—the business and social relationships—how do they influence decision-making in a generative board discussion? The above considerations suggest little room for the head to navigate, sell her ideas, develop tactical plans with the board chair, neutralize naysayers and most importantly put together a vision and strategy that is the product of research and deep thinking about where the school is and where it can be. Best idea wins, but only if the head and board chair can set up structures and practices that encourage this result. Generating vision and broad strategy is the responsibility of the head with help from the senior leadership team—in other words, people who are thinking about these big questions all the time: Where is the school now? Where can it go? How do we get there? Any structure that reduces the role of the head as chief strategist is suspect.

Pray tell then, if the board should avoid generative thinking in its purest form, what is the role of trustees when it comes to strategy? In the best boards I have seen, the trustees act as guardrails, stress testers, and alternate scenario generators. They use their expertise in their respective fields to either 1) help the head and her team reframe the strategic issues or 2) help the school achieve its strategic goals. The dynamic “give and take” among trustees is best reserved in committee meetings in which people with real expertise that may be transferrable to the issue at hand, feel comfortable speaking up and can help the head and senior leadership team refine their thinking or if necessary, go back to the drawing board. If heads can put trustees in a position to connect dots between their expertise and the school’s needs, then they are potentially adding value to the school. Steve Jobs’ quote on creativity is particularly relevant to boards: 

"Creativity is just connecting things. When you ask creative people how they did something, they feel a little guilty because they didn't really do it, they just saw something. It seemed obvious to them after a while."

Trustees can add value to decision-making when they draw on their own expertise and look for relevancy. (For a more detailed explanation of the value generated when ways of thinking are applied in new domains, check out David Epstein’s Range.) Increasing the odds of this happening derives from heads clearly and objectively framing issues so that trustees are more likely to see the relevancies and as a result, properly vet the strategic alternatives. Trustees can be generative, but it’s best when their contributions are in response to the head’s initial generative thinking. For this dynamic to work, the head has to 1) work closely with the Committee on Trustees to attract highly capable trustees and 2) possess enough humility to seek feedback on her initial framing. 

Building a talented board should be front and center for the head of school and the committee on trustees. But equally important is the deployment of that talent. That talent is best deployed when trustees are not doing the head’s work but rather vetting with expertise and humility and looking for relevant dot-connecting in order to add value to the school. Rod Snelling, the founder of Independent School Management, often said, “Sixty percent of what business executives know can be useful to independent schools; the other forty percent can do irreparable damage to them.” The teacher in me wants to embrace boards operating in the generative mode, but my instinct won’t let me.