management question

[Aliquid]

That would be the "CYOA" part. ;).

Regardless of whether something is dumb or not, for government work saying "that's dumb" outright probably isn't going to be the best approach.

Well yes, I suppose tact does matter. The message is the same, but the presentation matters. And you do need to judge the audience... is that the sort of person who will gossip? Is that the sort of person who will take this out of context. You really need to learn to read people.