The article I wrote at the end of last year, Table Stakes Aren't Strategy, generated quite a bit of interest and I appreciate all of those that reached out with such positive words. But you can never appeal to everyone and one reader wrote you can't tell a school serving 400 current families to go make a bold strategic pivot the way you'd tell a company to exit a product line. It’s a good point. And yet, embedded in the critique is the assumption that what I meant was that strategy requires discontinuity. It doesn't. What it requires is specificity.
My critic was responding to Roger Martin's strategy diagnostic — a strategic choice is one where the opposite isn't stupid on its face. It’s a good filter for catching table stakes dressed up as strategy. But Martin himself has pointed out a gap in it. A statement can pass the test and still not be strategic if it's pitched at a high enough altitude that almost any reasonable alternative would also sound absurd.
One example that Martin has used to illustrate his point is luxury hotels, and though I understand that schools are not hotels – even if they are the best of boarding schools – give me a moment to make the comparison.
Take a hotel chain that says its choice is to deliver a great guest experience. Flip it: choose a terrible guest experience? Obviously not. Martin’s test says this is strategic. But it isn't. Every credible luxury hotel chain would say the same thing. No choice has actually been made.
Now get specific. Say the same chain defines luxury not as grand architecture and lavish appointments but as restrained elegance where they anticipate and quietly compensate for whatever the guest left behind at home or the office — the charger, the pillow, the routine. Flip that, and the opposite isn't stupid at all. Two legitimate ways to win in the same category, pointed in different directions. That's a strategic choice, because a thoughtful, well-resourced competitor could look at the same market and reasonably choose the other one.
The lesson: vague choices always survive the opposite-isn't-stupid test, because vagueness has no real opposite. Specific choices are the ones that actually risk failing it and passing at that level of specificity is what makes something strategy rather than aspiration.
The reader who pushed back on the original piece heard "make strategic choices" as "consider abandoning what you currently do for the students you currently serve." That's a fair thing to react against and it's also not what the specificity test asks for. Nothing about it requires discontinuity, shrinking your mission, or turning away the families in front of you. It requires precision about how you serve them.
Most school strategic statements fail not because they're too bold, but because they're pitched at a Four-Seasons-says-great-guest-experience altitude. "Prepare students to thrive in a changing world." Flip it. Deliberately fail to prepare them? Nobody would choose that, so by the original test it reads as strategic. But it's just as empty as "great guest experience," for the same reason: every competitor school would sign the identical sentence, and nothing about how the school actually operates would need to change to be consistent with it. (And when I say “fail”, what I mean is that because the statement is not constrained, it does not provide the focus needed to take action in a way in which the entire community can align.)
Get specific, and the picture changes. A high school could define its version of preparation as depth over breadth. For example, two years of sustained, mentored independent research in a chosen discipline and an internship tied to the research area. Flip that, and the opposite isn't stupid: broad exposure across many disciplines, kept open as long as possible. Now you have two defensible bets in the same category, pointed in different directions. That's the moment a school has actually made a strategic choice not by pivoting away from its students, but by getting concrete about what it will emphasize, at their expense of what it won't.
The specificity test doesn't ask a school to become a different institution. It asks a school to stop describing itself in language so general that a hundred other schools could paste it into their own strategic plan without changing a word. You can make that kind of choice while keeping every student currently enrolled because it's a choice about emphasis and trade-off, not about who you serve.
There's a second concern that might emerge from the specificity test and it comes from a different direction than the first. Some readers might hear "get more specific" and assume it means the strategic plan itself needs to get longer — more initiatives and more five-year task lists, all specified in advance.
But that sprawl is not what the specificity test is asking for. It's actually the same failure as vagueness. A plan can be enormously detailed and still contain no strategic choice, if the detail is all tactical — a long list of things to do rather than a clear answer to what the school is choosing to be, at the expense of what it is choosing not to be. Length and specificity aren't the same thing. You can write four sentences that pin down a genuine strategic choice or forty pages that never do.
Go back to the hotel choosing to define luxury as compensating for what a guest left at home. That's one specific, durable sentence and it can hold steady for years. What flows from it — the turndown program, the concierge training, the amenities restocked in a room before a guest realizes they're missing — is tactical, and all of that should iterate constantly. Staff try things, keep what works, drop what doesn't, adjust to new guest expectations. None of that iteration requires touching the strategic choice, because the choice was never a list of programs. It was a specific bet about what luxury means, and the programs are just today's best guesses at delivering on it.
Applied to a school: the strategic choice might be a specific, durable statement — depth over breadth, two years of mentored independent research + internship as the school's defining academic experience. That sentence shouldn't change often, and it shouldn't need a hundred pages to say. What should change constantly, year over year, is the tactical work of delivering on it: which research mentors to recruit, how to schedule the time, what assessment looks like, how to communicate it to prospective families. A faculty committee should be free to try an approach, revise it, or scrap it entirely without anyone mistaking that as a strategic reversal because it isn't one. It's iteration in service of a choice that hasn't moved.