School Assignments Cannot Teach Critical Thinking

One time while I was at Microsoft I got assigned a newbie engineer to mentor. Let’s call him Sean. Nice Chinese guy. Quiet. Decent programmer. Just out of school.

I was reviewing some code that Sean had written and I noticed that in his code he had computed an average (arithmetic mean) composed of three different, heterogenous measures of quality for [complicated thing that’s outside the scope of this essay.]

This number he had generated— let’s be clear— was entirely, necessarily meaningless, as meaningless as the sum of “five kilograms plus three dollars”, and he had added a column in our database to track it. I gently pointed this out to him and asked what the deal was.

He shrugged. “I dunno. The project manager asked for it.”

“…why did he want the number?“

He shifted uncomfortably. “I dunno.”

“But it’s clear to you the number is meaningless, right?”

“I guess so? The project manager did say he wanted it.”

And thus, I had to explain to him the thing that I had to have explained to me when I was an intern, and which I feel like a lot of interns have to have explained to them: that work is different from school.

School, see, has a very interesting property compared to the real world, a property that almost nothing in the real world shares: assignments cannot be wrong. That is to say, if you are given an assignment in school, your job as a student is to do the assignment as written, ideally without question. If you’re in the more forward-thinking sort of school you might be able to ask without rebuke “why are we being given this assignment” but make no mistake: the assignment and its rubric won’t change because you asked this.

That’s because assignments in school are devised for one of precisely two reasons: “so that you learn the relevant material” and “so that it can be graded, to rank you against the other students.” There is no other reason for any school assignment to exist.

And that means the specific form of the assignment is very nearly irrelevant. “Learn how addition works” is achievable by any series of addition problems; one addition problem isn’t really “better” than another. And for the purpose of grading, the specific assignment given matters still less: anything with a rubric will do.

That’s why even naturally-curious students lose the impulse to ask “why are we being given this assignment.” From their perspective, and from the perspective of the school, the question is pointless: one assignment is as good as another and a student asking “why this one” sucks up class time while never producing useful information.

Now enter the working world.

Suddenly, assignments aren’t arbitrary. Frequently they’re underspecified; occasionally they’re entirely incorrect. That’s because the goal of the work assignment isn’t “turn this in for a grade at which point you the work product is hurled into a dumpster;” it’s “make money for the business” or “ensure we are in compliance for xyz regulation” or “ensure we are secure against cyberattacks.“

If your manager asks you to create a database and the thing he actually wants is to be able to stop losing track of inventory for unclear reasons, then the assignment he gave you— “create a database”— is correct precisely insofar as it lets him achieve his actual goals, and “checking the explicit spec against your manager’s actual goals” is one of the things differentiating senior engineers from interns.

That’s one of the most important things, in fact.

Any time you are doing work that is for a distinct and non-interchangeable ultimate goal, you are not doing schoolwork. You are doing work. Alternatively, you might be doing a very complex hobby.

For that reason, I think people who mourn that students aren’t getting taught critical thinking in school are making a category error: to the extent that critical thinking is about “understanding the relationship between means and ends and what the right thing to do is in a given situation” as opposed to just “identify the logical fallacies present in this one-page opinion piece,” we’ve officially left the realm of school and entered the realm of every non-school domain in life.

We have 25-year-olds who can’t do basic forms of means-end reasoning because we suck up so much of their time in school-shaped learning that the first time kids ever have to do means-end reasoning is after graduation, well into adulthood.

I have no specific policy prescription here, beyond that “make schools teach critical thinking” is very nearly a category error.

Becuase school may be, in fact, the only institution that can’t teach critical thinking.

I think the operative question is always this:

“Can the worker be dinged (even implicitly) for doing precisely what the supervisor told him, and not inferring that something different was needed?”

If the answer is “yes,” then sure: you have a genuine situation where you’re able to teach the meta-skill of evaluating the spec you’ve been given and checking it against whether it’s what is actually needed. I’ll note that the real world does give you a “yes” answer to this question: in the above anecdote, the intern did in fact get (very gently) told off for doing what he had been told, because the job spec of software engineer is not “do what you are told.” It is “satisfy the business objective.”

If the answer is “no,” then you’re just doing a very gussied-up version of the prototypical school-shaped job: “you did good if and only if you did precisely what you were told to do.”

Not generally, no.

Consider: students can appeal grades. They can do this because grades are meant to be “fair”, and “fair” means “consistent with what was announced in advance as the grading criteria”.

What you are doing, structurally, in work-shaped environments is that you are disregarding fairness in evaluating work outputs. “Good” is defined as “the job got done in a way consistent with the meta-goals of the job regardless of what the supervisor told you directly.”

Now compare this with school.

Each step follows directly: grades have to be fair → fairness requires criteria you’ve announced in advance, which applies to each student individually → therefore the evaluation has to be according to these criteria → therefore the criteria cannot be wrong.

And why does school have to be fair? Because schools are institutions where a primary purpose is evaluation, and anything with that primary purpose will end up school-shaped in this way.

You can see this operate from the other direction in the workplace: all the megacorporations I’ve worked at— Microsoft, Amazon, Expedia— have crafted elaborate pseudo-objective grading rubrics for precisely one part of their work environment: promotions and performance evaluation. This is, not coincidentally, the part of the job that is the most obviously farcical: almost none of what engineers do can be objectively evaluated, so these rubrics mostly serve to launder a huge variety of subjective judgments made by the engineers and managers on the promotion panel. But large companies sense that the appearance of fairness is deeply necessary in evaluative environments, which is how these rubrics get devised in the first place.

(Notably, the reason this is allowed to be clearly a farcical veneer over subjective judgment is because at work there is no appeal. You can’t drag your promo panel in front of an adjudicator and be like “PER CRITERION 3B I DEMONSTRABLY HAVE MET THE BAR FOR SENIOR ENGINEER.” The rubric structures the conversation but it doesn’t bind anyone. Which is good because I think basically everyone at these megacorporations knows that objective promotion criteria can and do get gamed: anyone remember that brief period where giant companies were rewarding employees directly for ai-tokens-consumed? Extremely funny, very predictable results, no notes.)

Of course, that just means the thing that everyone already knew: promotions are, always and everywhere, popularity contests. The primary difference between healthy and toxic work environments is whether popularity is meaningfully connected with how well you helped achieve the organization’s objectives.

Okay, yeah, you got me. Those are exempt and can be work-shaped.

(Good luck getting the students to do them.)