Telling someone their idea won’t work, kindly and early, is braver than letting them find out at launch.

Saying nothing feels like kindness and is mostly self-protection. You avoid an awkward ten minutes, and they spend three months and their own money finding out what you already suspected, which is a much worse conversation when it arrives. Early doubt is a gift precisely because it is cheap to act on.

If you have a real concern about somebody’s plan, say it once, specifically, while they can still change course. Name the part you think breaks rather than the whole thing. Then back whatever they decide, since having said it honestly is the whole job.