A Question Called 'Is It Possible?'

“It should work”

There’s a question you hear a lot at work: “Is X possible?” And an answer you hear just as often: “It should work.” “That seems hard.”

On the surface it’s a perfectly normal exchange — a question asked, an answer given. But I’d say nothing actually happened there. The person who asked got no grounds for a decision, and the person who answered just voiced a hunch. Yet the meeting moves on to the next item on the strength of that one remark, and a few weeks later someone ends up saying “but you said it would work.”

Half of it is down to asking that way. “Is it possible?” carries an assumption that everything in the world falls neatly into possible or impossible, and in reality the answer is almost always somewhere in between.

Possibility is not an opinion

For some X to be possible, several conditions usually have to hold at once. Call them A, B, C, D, and E. Take them apart one by one and they tend to split three ways: things that work today, things that work if you spend money and time, and things there’s simply no way to do.

A and B work today. C and D cost something, but nothing rules them out. E, though, has no path with current technology. Then the answer about X falls out on its own: “not possible right now, because of E.”

There’s quite a gap between that answer and “that seems hard.” An answer that came out of working through the conditions is one other people can retrace and check — is anything missing from the list, is E really a dead end, they can go through it point by point. An answer that came out of a hunch has nothing to check. The only thing that can stand up to a hunch is another hunch, so all you get back is “well, I think it’ll work.”

So possibility is less something you settle by opinion than something you work out by going through conditions one at a time. Which means you shouldn’t be carrying the answer around memorized; you should be able to work it out each time.

A duel of hunches

Everyone has seen how a meeting goes when only conclusions get exchanged, with no conditions attached.

The moment “it should work” collides with “that seems hard,” the meeting stops trading reasons and starts arm-wrestling with hunches. Hunches can’t check each other, so the contest gets decided by all the wrong things: whose voice is louder, who has more seniority, who looks more confident. And a conclusion settled that way starts wobbling as soon as people walk out of the room.

Lay the conditions out and talk about those, and the same argument plays out differently. “I’m negative on this because C looks hard” against “couldn’t we solve C this way?” is a healthy collision — it’s a dispute you can settle by checking. What’s left at the end of the meeting isn’t “who won” but a piece of work: “let’s find out what C actually costs.” Clashes of opinion turning into work like that is the biggest thing laying out the conditions changes about a meeting.

Sooner or later it starts working

Taking it apart gives you one more thing, and I’d say this one matters more: you learn when the answer changes.

“Not possible right now, because of E” has the words “right now” sitting in it. Once E comes unstuck, X stops being a question of whether it can be done and becomes a question of how much you’re willing to spend. And looking back at the history of technology, E comes unstuck more often than you’d think. When GPS and mobile internet landed on smartphones, “hail a passing car with an app” went from fantasy to business. When LLM inference costs dropped by orders of magnitude, products that had been impossible to build on top of them poured out. The people who had memorized only the conclusion walked right past the moment the condition gave way.

So I like to compress all of this into one line: cache the conditions, not the conclusion.

Store only the conclusion “X is impossible,” and that cache never expires, no matter how much the world changes. Years later, whenever X comes up, “that won’t work” fires off reflexively. But if you’re holding it with the condition attached — “X doesn’t work because of E” — a news item skimmed in passing catches your eye. A price cut, a newly opened API, a regulation change, and you notice on your own: “huh, E just got unblocked. Time to look at X again.” That’s where the difference comes from, between the person who lets the same news slide past and the person who reads an opportunity in it.

The weight of saying yes or no

None of this means the question “is X possible?” is itself bad. Someone who doesn’t know asking someone who does is only natural, and for a junior, asking it is part of learning. But when a senior passes that question along to the next person without breaking it down, that’s a different matter. Splitting a question into conditions is precisely the work expected of a senior. The same sentence is a question from one person and, from another, an act of handing off their own job.

And the more you sit in a seat where judgments get made, the more of this weight you carry. Saying yes or no is, in itself, deciding where other people’s time goes. A leader who says “impossible” without breaking it down erases options the team could have had; a leader who says “possible” without breaking it down makes promises the team will have to keep. Either way the price is paid not by the one who ruled, but by the ones who execute.

In the end what people keep trusting are the judgments you can check. Put the conditions out alongside it and others can go through them one by one, and when it still holds up after that, trust starts to form. A title gets people to listen, at least at first, but that’s a bit different from trust. Trust only piles up after it has come through that checking a few times.

Even so

That said, taking it apart doesn’t produce the right answer either.

The condition list itself can be wrong. You might lay out A through E, work through all of them, and find there was a hidden condition F all along. The E you declared impossible might turn out to have a workaround. You don’t always have time to take every judgment apart, and some decisions are rightly made fast, on gut feel.

But a judgment you took apart, even when it’s wrong, lets you trace where it went wrong. A condition list can be fixed, and the fixed list gets reused in the next judgment. A hunch leaves nothing behind when it misses. With no material to review beyond “that’s what I thought at the time,” you can repeat the same mistake without ever noticing.

So decomposition is less a technique for being right than a technique for leaving your judgment in a form you can learn from when you’re wrong. The more people speak that way, the more meetings shift from duels of hunches toward working through the conditions. And I believe it’s the conclusions from those meetings that survive outside the room.