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“A society grows great when old people plant trees in whose shade they shall never sit.” — Greek Proverb
Here are some leadership questions worth asking with regularity, even when (and especially when) the problems of the moment are eating up all of your attention:
Which of your current decisions will make things easier for your school in the future?
Which of your current decisions are creating future optionality for your school?
These questions deliberately prompt you to switch frames — short-term to long-term and long-term back to short-term — as a regular habit of mind. They also serve as a gentler form of Chekov’s hammer, which essentially advises that the good times are often the most dangerous times for an individual or an institution. Not to get too gloomy, but a hungry competitor is always scheming and an unknown unknown is always developing on the far horizon.
Acting accordingly need not be stressful, and one of the best ways to do so is to draw attention, if not new funds, to your school’s endowment. An endowment is like a purposeful tree — no amount of engineering, money, or magic can make it grow instantly into the future provider (of fruit, of flower, of shade, of oxygen) that the planter aims it to be. It is also a beacon for inclusivity — anyone who cares about the school, whether currently or formerly connected, can contribute at any at level they are able to.
Of course there is a problem of perception baked into any such ask. Though independent school endowments are likely their best long-term planning/strategic levers, most schools’ current community members will not benefit at all in the short term from giving them attention (or funding). Seeing the impact of one’s gift to an endowment requires some imagination.
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